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Um, hello Brooke. I'm working on my album. Um,  I just want to say hello and I hope I get to see   00:00
you soon. Just a brief message on video. Goodbye.  Michael Jackson once said Brook Shields was one of   00:08
the loves of his life. He told the world they were  dating, that they were in love. But according to   00:15
Brooke, that wasn't true. For years, the two  were photographed side by side. award shows,   00:21
red carpets, private dinners, creating the image  of a Hollywood couple at the height of Jackson's   00:27
fame. But their relationship never quite made  sense. They were always seen together. Yet,   00:33
no one could ever say for certain what they  actually were. They admitted to having feelings   00:39
for each other, but stopped short of defining  it. Two people shaped by fame from childhood   00:43
trying to navigate relationships, identity, and  normality in a world that never allowed it. Were   00:50
they genuine love interests, close friends,  or part of something much more calculated?   00:56
Because the truth is, their relationship  was never what it seemed. Here's the detail. 01:02
The very first time the two met was at the 1981  Academy Awards, an event that Michael Jackson   01:14
attended with Diana Ross as his date. Brooke saw  the superstar singer from across the room and   01:20
urged by her mother and manager Terry Shields, who  encouraged Brooke to socialize with celebrities at   01:26
such star-studded events, the 15-year-old boldly  went straight up to Michael and introduced herself   01:31
and asked him if he wanted to dance with her.  Michael Jackson later recalled the encounter.   01:37
Quote, "Before meeting her, her pictures were  all over my walls and mirrors. She just came up   01:43
to me and said, "Hi, I'm Brooke Shields. Are you  going to the afterparty?" I said, "Yeah." And I   01:48
just melted. I was about 23 during Off the Wall.  I thought, "Does she know that photographs of her   01:54
are all over my room?" And we went on the dance  floor. And man, we exchanged numbers and I was   02:01
up all night spinning around in my room just so  happy. From that first meeting, Michael Jackson   02:07
and Brook Shields formed an immediate connection.  What began as a chance encounter quickly turned   02:14
into a close, almost instinctive friendship.  By 1981, both were already global figures.   02:19
But their paths to fame had come at a cost.  Like Michael, Brook Shields had been working   02:26
for most of her life. Thrust into the spotlight as  a child, her early film roles, often provocative   02:32
and controversial, made her one of the most talked  about young stars in the world. At the same time,   02:38
her modeling career exploded. Her Calvin  Klein campaign didn't just make headlines,   02:44
it reshaped the brand entirely, reportedly driving  sales to unprecedented levels. By the early 80s,   02:49
she wasn't just famous. She was a cultural symbol,  even being labeled the face of the decade by Time   02:56
magazine. But behind that image was a reality  that mirrored Michael's in striking ways. Both   03:02
were products of intense parental control. Brook's  career was managed by her mother, Terry Shields,   03:09
a dominant, often overbearing presence whose  struggles with alcoholism added another layer   03:15
of instability. Their relationship was deeply  codependent, blurring the line between protection   03:20
and control. Michael's upbringing followed a  similarly complicated pattern. Driven relentlessly   03:26
by his father, Joe Jackson, he had been pushed  into stardom from a young age. While his mother,   03:32
Catherine, represented a quieter, more protective  force. Someone who wanted a sense of normality for   03:37
her children, even as their lives became anything  but normal. I was 13, I think, when I first met   03:43
him. and we were fans of each others and we just  immediately hit it off. We laughed so hard. I   03:50
didn't I wasn't trying to get a music career. I  wasn't trying to get anything from him and we just   03:59
started hanging out. She would often visit him  unannounced at his family's Havenhurst estate,   04:04
making both his sisters, Latoya and Janet, so  jealous that they tore down Michael's pictures   04:10
of the starlet and called her giraffe butt  behind her back. They found a common bond.   04:15
Michael always felt that unless someone  had sacrificed their childhood for stardom,   04:21
they could never really understand him. That is  why he was so drawn to people like Brooke as well   04:25
as later on with the likes of Elizabeth Taylor and  Macaulay Kulkin, choosing to surround himself with   04:31
former child stars old and new. I think because  we both grew up in this in the same business and   04:36
we had similar upbringings in the sense that we  were you know we we had to begin in this business   04:42
at a very young age. We learned a sense of uh we  had defense mechanisms that we had built up and I   04:48
think once we met each other we realized that we  didn't really have to be wary of one another and   04:54
that just that enabled us to build a friendship on  a very different level. Even though she was only   04:59
a teenager, Brook Shields already embodied the  presence of a classic movie star. She was elegant,   05:04
classy, pure, and well-mannered. All the qualities  that Michael Jackson valued and that he admired in   05:10
other women like his Mottown friend Diana Ross as  well as Princess Diana. In both cases, childhood   05:16
had been sacrificed for success. They weren't  just young stars. They were providers. Both   05:23
carried the weight of expectation, functioning  as the financial backbone of their families   05:30
while navigating an adult world long before  they were ready. And yet, despite everything,   05:34
there was a shared innocence between them. Away  from the cameras and public personas, both Michael   05:40
and Brooke retained a kind of childlike escapism.  They were playful, imaginative, and in many ways,   05:46
still searching for the childhood they never  fully had. With each other, they found a rare   05:52
sense of ease. a space where they could drop the  performance, step outside the pressures of fame,   05:58
and simply exist as themselves. As Michael's  fame reached unprecedented heights following   06:03
the release of Thriller in 1982, Terry  Shields, ever the calculating stage mother,   06:09
recognized the opportunity, aligning Brooke with  the world's biggest star, could only elevate her   06:15
daughter's already rising profile. Therefore,  she encouraged her daughter to make more public   06:20
appearances with the pop superstar, and the  pair became a headline grabbing duo at many   06:25
high-profile events, a carefully managed image  that blurred the line between genuine friendship   06:30
and strategic publicity. Speaking about their  relationship, Michael Jackson recalled that,   06:35
quote, "Broo Shields asked me out every time you  saw us out together. It was her idea to go out and   06:42
do it every time. I sincerely liked Brook Shields,  too. I liked her a lot. Brook Shields was one of   06:48
the loves of my life and we dated a lot. Although  Brooke helped instigate their public appearances,   06:54
the dynamic quickly worked in both their favor.  For Michael, the timing was crucial. After   07:00
Thriller, his fame reached another level. But  so did the scrutiny. Tabloid rumors about his   07:05
personal life, particularly around his sexuality,  were becoming harder to ignore. Being seen   07:11
alongside Brooke Shields, one of the most famous  and desired young women in the world, offered a   07:17
powerful counter image. It reframed how the public  saw him. Brooke, in many ways, was the perfect fit   07:23
for that role. She was already an established  star, but still carried that all-American   07:29
youthful innocence that made the pairing feel  natural and believable. Whether romantic or not,   07:34
it looked right. But beyond the optics, Michael  trusted her. Brooke understood fame. She knew how   07:40
to handle attention, how to protect her image,  and crucially, how to keep things private. For   07:47
someone as guarded as Michael was becoming, that  mattered. He could step out with her knowing she   07:53
wouldn't exploit the moment or get overwhelmed  by the media storm around them. It also gave   08:00
him a sense of support at a time when everything  around him was intensifying. She was a familiar,   08:05
steady presence in very public spaces. There was  also a broader cultural layer as Michael's music   08:11
crossed further into mainstream predominantly  white audiences. Being linked to Brooke subtly   08:18
helped ease that transition. It softened his image  for parts of the public and industry that hadn't   08:23
fully embraced him before. In the end, their  relationship sat in that gray area between genuine   08:28
connection and image making. But at that point  in their careers, it worked for both of them.   08:34
If you wanted to pick up the phone and and call  Michael Jackson, can you can you dial Pluto direct   08:42
or or what's what's the Could you reach him like  other Earthlings couldn't? Yes, I could. Now, let   08:47
me cuz you actually you have been out on several  dates with Mr. Jackson. Is that right? Michael and   08:53
I have been friends for years. And I was like the  the person that he would call because these other   08:57
famous people would sort of really like prey on  him and want to be like I'm going to sleep with   09:03
him because that's going to be a thing. However,  the lines between reality and tabloid fantasy   09:07
would begin to blur. After the 1984 Grammys,  where Michael won a record eight awards, he hosted   09:14
a private party at a downtown restaurant. But  despite the celebrations, he and Brooke slipped   09:21
away early, leaving around 11:30 p.m. Michael  drove Brooke and her mother back to their hotel,   09:26
then went home himself, leaving Brooke  disappointed that he wasn't going to stay the   09:32
night. At the time, they were widely described as  dating, but what actually existed between them was   09:37
far less defined. Over the years, both admitted  there was mutual attraction. Yet, neither ever   09:43
gave a clear answer on whether their relationship  became physical. Perhaps that ambiguity was   09:49
intentional, something that kept them in the  headlines, or maybe it simply reflected their   09:55
own uncertainty. As Brookke said at the time,  quote, "It's hard to say if it's platonic or not.   10:00
We've both had crushes on each other at times.  Despite her public image, Brooke was relatively   10:06
naive when it came to relationships. Her career  had projected a highly sexualized persona from a   10:13
young age. Yet, in reality, she remained cautious  and reserved. Like Michael, many of her closest   10:20
connections began as deep platonic bonds. She  has since explained that her Catholic upbringing,   10:27
combined with the pressures and overexposure  of fame, left her inhibited when it came to   10:32
exploring her sexuality. Michael, meanwhile,  seemed to view her very differently from how   10:37
the public did. While Brooke struggled privately  with body image and her own sense of identity,   10:43
Michael placed her on a pedestal. He reportedly  expressed that he wouldn't want to sleep with   10:49
someone unless he intended to marry them.  In his eyes, Brooke was almost untouchable.   10:54
something pure he didn't want to damage. And yet  there were moments where that boundary nearly   10:59
shifted. Brooke became increasingly curious about  sex. And by her own admission, more interested in   11:05
Michael than she publicly let on, perhaps because  he felt safe, someone who wouldn't push things too   11:12
far. In his autobiography, Moonwalk, Michael  described their relationship as romantically   11:17
serious for a while, later recalling an encounter  where things became more intimate. but he pulled   11:23
back. Quote, "We had one encounter when she got  real intimate and I chickenened out." He said,   11:29
"And I shouldn't have." In many ways, their  relationship remained suspended in that space.   11:35
Somewhere between friendship, attraction, and  something neither of them fully acted on. I mean,   11:41
he's just he's a very soft sort of voice, and he  always says, "Oh, Brooke, I'm so he's always so   11:47
happy to talk to you and he wants to know what  you know what you're doing." And but he's very   11:52
um actually there is no butt. There's just a  a a very genuine innocence that he has that he   11:56
has protected and sheltered himself from so much  that that's been maintained. He has an innocence   12:03
about him that just enables him to revel in in  flowers and children and animals and and he's   12:11
just I mean he talks about his work a little bit  but he really just talks about things that make   12:17
him happy. I mean we we have long discussions  just about everything. So he's quite a regular   12:21
person. He really is. And he's well regular in the  sense that not regular in the sense that he's not   12:25
jaded. Yeah. And I I find that many people in this  business have a tendency it's it's easy to become   12:30
jaded. I mean, people talked about his genius,  but I don't think they talked they didn't really   12:35
know how polarized his sort of life was in so far  as he was extraordinarily a genius and talented   12:40
and he was there was an arrested development I  believe and he was sort of truncated emotionally   12:49
as a little kid and he was a child. He was he  was childlike but but in many ways and we were   12:57
kids together. I think that there was an arrested  development to a certain extent with him in in   13:05
that way but we we act like we acted like little  kids together and I don't think either one of us   13:11
in our lives really had the environment to do that  safely. After the thriller era and the height of   13:16
their public association, both Michael Jackson and  Brook Shields entered a period of transformation,   13:24
each in their own way was trying to take back  control of their life and identity. But the paths   13:30
they chose couldn't have been more different. For  Brooke, it meant stepping away from the industry   13:36
entirely. She enrolled at Princeton University, a  deliberate move to break free from the world she'd   13:42
grown up in and from her mother's control. College  gave her something she'd never really had. Space.   13:48
Space to grow. To form real relationships outside  of Hollywood and to figure out who she was beyond   13:55
the image that had been built around her. For  Michael, independence didn't mean entering the   14:01
real world. It meant creating one of his own. He  began asserting control over every aspect of his   14:09
career, taking charge of his management, building  business ventures, surrounding himself with   14:15
lawyers and trusted collaborators. His ambition  was clear, not just to succeed, but to become   14:20
the biggest star in the world. Where Brooke sought  normality, Michael doubled down on exceptionalism.   14:27
Brooke later recalled how fascinated he was by  her decision to go to college almost in disbelief   14:34
that such a life existed as she began experiencing  relationships and intimacy. She would confide in   14:40
him and his reactions revealed just how sheltered  he'd been. Quote, "He was like a little kid,"   14:46
she said, talking about what first base was, what  second base was. It was a world he simply couldn't   14:53
relate to. as she later reflected, quote, I went  to high school and college and forced that into my   15:00
life. He didn't have that luxury, I think it just  always felt too unattainable for him. By the time   15:07
Brooke graduated in 1987, she had changed. She was  more confident, more grounded, no longer just the   15:14
image the world had projected onto her. She had  experienced real relationships, even losing her   15:21
virginity to her college boyfriend, Dean Kaine.  Michael, however, seemed to remain emotionally   15:27
in the same place. He would occasionally talk  about the idea of them marrying and raising   15:32
children together. But by that point, Brooke saw  things differently. Having experienced genuine   15:37
romantic love, she knew what she wanted and what  this wasn't. She later admitted that marrying   15:43
Michael would have divided her life too much.  She still believed in the idea of a fairy tale,   15:49
but one rooted in real love. And deep down, she  knew Michael wasn't truly in love with her. Quote,   15:54
"There were times when he would ask me to marry  him," she said. "And I'd tell him, "You have me   16:01
for the rest of your life. You don't need to  marry me. I'm going to have my own marriage,   16:07
my own kids, and you'll always have me." In  many ways, their dynamic had shifted. Brooke had   16:11
grown up. Michael hadn't. She moved forward into  adulthood, relationships, independence, reality.   16:18
While Michael remained suspended in a world of  his own making, still chasing something just out   16:25
of reach. Like Wendy leaving Neverland while Peter  Pan stayed behind. I mean, I remember saying this   16:30
to him. He He couldn't believe I was going to go  to schools. He couldn't believe I was going to go   16:37
to regular schools, that I was going to go away  to college by myself, that I was going to then   16:42
when I told him I was getting married, he was he  just didn't get it. He was like, "You what? You   16:47
can't do that." And I said, "I've got a chance."  I said, "I've been going out in the world. I'm not   16:52
so isolated, and I want I want this chance.  I want a chance to be quote unquote normal,   16:57
you know, and it and he never really could trust  a lot of people around him." Despite the shift   17:03
in their dynamic, Michael and Brooke remained  close in the years that followed. In 1991, Brooke   17:10
attended Elizabeth Taylor's seventh wedding as  Michael's date held at his Neverland Ranch estate.   17:16
Around the same time, Slash recalled being  introduced to Brooke by Michael as his girlfriend   17:23
before Jackson left them in the studio to take her  out to dinner. Their outings became something of a   17:29
spectacle. As Brooke later put it, quote, "We used  to go out to restaurants. It was madness. Getting   17:35
in and out was chaos, but once we were inside,  we could just sit and be normal for a moment."   17:42
That balance between chaos and normality defined  their public relationship, but there was also   17:48
a growing sense that the attention wasn't  entirely accidental. In later interviews,   17:54
Brooke suggested that Michael may have tipped  off photographers, aware of the publicity their   17:59
appearances together would generate, and at  that stage in her career, that visibility   18:04
wasn't unwelcome. After graduating, Brooke had  struggled to reestablish herself in Hollywood.   18:09
Casting opportunities were limited and the  industry didn't quite know where to place   18:15
her anymore. Being seen alongside Michael, still  one of the most photographed people in the world,   18:19
kept her in the headlines and crucially kept her  relevant. Together, they leaned back into the   18:25
image they had once created, playing their roles  in front of the cameras, even as the nature of   18:31
their relationship had changed. But as the years  went on, the tone around Michael began to shift.   18:36
Media scrutiny intensified, becoming more invasive  and at times openly critical. And increasingly,   18:43
Brooke found herself being asked to speak on his  behalf. Put in a position where she felt she had   18:50
to defend him not just as a public figure, but  as a friend. When you're in his presence, and I   18:55
don't mean this tongue and cheek at all, is there  something eerie about him? No, it's not eerie in   19:01
the sense of uh scary or weird. He's so creative.  I mean he's he borders on genius. And I think that   19:07
when you are you have that much talent and you  are at the same time that sensitive of a person,   19:16
you your conversation is going to be different  with him. And I think that that's where one   19:23
might interpret it as eerie. It's not. It's not  though. and all it takes is a joke or laughing   19:28
or talking to him or you know saying look I'm I'm  here too and you're hearing do the uh unfortunate   19:34
nasty comments and criticisms about him do they  upset you make you they upset me constantly I'm   19:40
constantly upset by what people say I mean first  of all people so many people really don't know   19:46
him and they don't give him a chance and they're  so ready to criticize and I think what happens is   19:52
when you see genius and when you see a talent that  is just unstoppable and untouchable. The first   19:57
reaction people have is to criticize it because it  scares them. It threatens them and it sort of it   20:04
um in order to augment their own selfworth, they  feel that they have to belittle him. And you know,   20:09
he's a sensitive human being who this this all  of the negativity really it does affect him and   20:14
it hurts him. How how do you recognize him between  dates? How do you know it's him coming up? because   20:20
he does look very different now, don't he? He He  does look different. We We don't ever discuss any   20:29
of that actually. We talk a lot on the phone, so  it's usually his voice that gives him away. But do   20:35
you do you find yourself biting your lips saying,  "The man has a completely different nose." And   20:40
then you go, "What a terrific weather we've been  having, Michael." How do you avoid the issue? We   20:45
It's It's not something that you just really want  to ever talk about or dwell on. But we actually   20:51
for the wedding we were um I mean it was really  interesting because I was there from the Oh,   20:56
so we're back to the wedding now. So yeah, light  segue. Yeah. Um yeah, the wedding. How big is   21:00
Michael Jackson's willing? I think you should ask  Michael Jackson. That's my thing I'll never find   21:07
out. However, while Brooke had always been careful  to keep their relationship private, Michael   21:14
appeared to cross that line himself during his  1993 sit-down interview with Oprah Winfrey. When   21:20
asked about his personal life, Michael claimed  he was dating and in love with Brooke Shields,   21:26
adding that they kept things out of the public eye  to maintain privacy. Do you go out? Do you date?   21:33
Yes. Who do you date? Well, right now it's Brooks  Shields. Mhm. That's I don't Well, we try not to   21:39
just be everywhere and go every It's mostly at  home. She'll come over. I'll go to her house cuz I   21:48
don't like going out in the public. Have you ever  been in love? Yeah. Mhm. With Brook Shields? Yes.   21:53
And another girl. And another girl. The problem  was Brooke was in no way dating him at the time.   22:00
She was in a relationship with her future husband,  Andre Agassi. According to later accounts,   22:08
after watching the interview, she called Michael  and demanded to know what he was doing. From   22:13
her perspective, the line between suggestion and  reality had been pushed too far. On the surface,   22:18
it looked like a clear fabrication, a calculated  move to soften Michael's image and steer attention   22:25
away from growing scrutiny. But the situation  wasn't entirely one-sided. Earlier that same day,   22:30
Brooke had appeared on Oprah's show herself and  notably didn't shut down any romance speculation.   22:37
Instead, she hovered in that familiar gray  area, neither confirming nor denying anything,   22:44
allowing the idea of them as a couple to linger  in the public imagination. I want to know what   22:50
the real deal is, Brooke, between the two of you.  Was there was there romance going on? Were you all   22:56
kind of romantically involved? Was there like ever  an exchange of, you know, rings or anything or   23:02
um Well, actually, I think right now, let me say  that I believe that we're closer now than we ever   23:11
were. I think we love each other more now than we  even knew we did when we were younger. Really? We   23:16
We used to Well, because we had fun when we  were younger. I mean, it was And we were sort   23:22
of a source of relief. This is a question. Did you  have a crush on him or did he have a crush on you?   23:26
I think we both had a crush and still do have  a crush on each other. I mean, I think part of   23:32
having a crush on someone is admiring them almost.  I mean, you have we have a lot of fun together. I   23:36
mean, it's almost unfortunate cuz we know each  other so well. But, I mean, he just he amazes   23:43
me every time I sit down and talk to him about  something really. Does he feel does he feel more   23:48
like a brother to you though than say a boyfriend  though? It's hard to say. I mean, I I find it's a   23:53
love on a different level. I mean, I feel closer  to him than the some of the boyfriends that   24:00
I've had. It was a pattern they had fallen into  before. Whether it was a quiet favor to Michael,   24:08
helping reinforce a more conventional  image, or something that also served Brooke,   24:14
who at the time was struggling to regain momentum  in her acting career. Brooke had always preferred   24:18
to keep things deliberately vague. So when Michael  suddenly went public claiming they were dating and   24:23
in love on one of the most watched interviews  ever, it crossed a line she hadn't agreed to.   24:29
Therefore, she firmly denied the claim in the  press. The confession didn't appear to damage   24:35
their relationship as just weeks later, Brooke  accompanied Michael to the 1993 Grammys where he   24:41
received the Grammy Legend Award from his sister  Janet Jackson. It felt almost nostalgic, echoing   24:48
their appearance together nearly a decade earlier.  Around this time, Michael also gave Brooke a ring.   24:54
She later recalled how he casually threw the  box towards her. Inside was a large diamond   25:00
encrusted ring. Unsure how to interpret it, she  asked what it meant. Michael simply told her,   25:06
"I just want to show that I love you and that  I care for you." For him, it was a gesture of   25:12
affection. For Brooke, it was something harder  to define, much like their relationship itself. 25:19
However, just months later, Michael Jackson  found himself at the center of a media storm   25:28
following allegations made by a 13-year-old  boy. Jackson faced intense public scrutiny. The   25:33
press coverage was relentless. Sponsors began to  distance themselves, and his commercial momentum   25:39
started to falter. Behind the scenes, there was  growing pressure to repair his image and fast. One   25:44
widely discussed strategy was simple marriage. The  thinking was that presenting a more conventional   25:51
heterosexual image could help counter the  narrative forming around him. During this period,   25:58
Michael reportedly made a serious proposal  to Brooke, the woman he'd been most closely   26:04
linked to for over a decade, a familiar figure  who had helped steady his image during periods   26:08
of speculation. But by then that dynamic was gone.  Brooke was in her late 20s in a relationship with   26:13
Andre Agassi, someone she was genuinely in love  with. And she had begun to distance herself from   26:21
the Hollywood world she'd grown up in. She wanted  something more grounded, more private, and she   26:26
understood the weight of what Michael was facing.  Even before the allegations, his life came with   26:33
a level of scrutiny she no longer wanted to be  part of. So she said no. It was a turning point.   26:38
Shortly after, Michael turned his attention  elsewhere, proposing instead to Lisa Marie   26:45
Presley, who accepted. Their marriage, announced  in 1994, would become one of the most talked   26:50
about and scrutinized relationships of the  decade. When asked about Michael Jackson's   26:56
marriage to Lisa Marie, Brooks stated, quote,  I think we're not dealing with convention. So,   27:01
somebody like Michael, he's not going to just  fall in love with somebody and get married.   27:07
I think there were a few people that he could  identify with. And what I know about Lisa Marie,   27:12
she was very sweet. She could identify with him.  They could talk about things that I'm sure she   27:16
understood with regards to her father. Brook's  rejection of Michael's proposal effectively ended   27:21
the public dynamic they had built together.  From that point on, the two gradually lost   27:29
touch. Life moved on. Brooke remarried in 2001 and  started a family. But behind the scenes, she was   27:34
struggling. After the birth of her first child,  she experienced severe postpartum depression. When   27:42
she spoke publicly about it, Michael reached  out, sending flowers. Despite the distance,   27:47
there was still a thread connecting them. Quote,  "At every major event in my life, he reached out."   27:53
She later said, "When my dad died, when I had  my first daughter, we'd speak. But over time,   27:59
it became harder to reach him. the people around  him changed and in the last few years it was   28:06
difficult to even get through to him. Her concern  for him never really went away. Quote, "I was   28:12
worried about him financially. I was worried about  the kids. I was worried about his health. I always   28:19
worried about his health because I thought he was  just too skinny." Even as their lives diverged,   28:25
there was still a sense of care, a quiet,  lingering connection that never fully disappeared.   28:31
Did you remain friends throughout? Throughout. He  was the first person to call me when my dad got   28:38
sick. Wow. He, you know, when I had postpartum,  he, you know, he sent me flowers and, you know,   28:44
all of these things even though we sort of  hadn't had our regular dinners that we used   28:51
to have on a more regular basis. Um, but he was  the he was consistent. By the time of Michael   28:57
Jackson's death in 2009, the two hadn't been seen  together publicly for over 16 years. And yet,   29:04
the connection clearly remained. At the request  of Michael's mother, Catherine Jackson, Brooke   29:11
was asked to speak at his public memorial at the  Staples Center in Los Angeles. What followed was   29:16
one of the most emotional and memorable moments  of the service. Reflecting on their relationship,   29:22
she said, quote, "Whenever we were out together,  the caption usually said something like, "An odd   29:28
couple or an unlikely pair." But to us, it was the  most natural and easiest of friendships. Michael   29:34
always knew he could count on me to support him or  be his date, and that we would have fun no matter   29:41
where we were. We had a bond. Both of us needed to  be adults very early, but when we were together,   29:46
we were two little kids having fun. To the outside  world, Michael was a genius with unchallenged   29:53
ability. To the people who were lucky enough to  know him personally, he was caring and funny,   30:02
honest, pure, non-jaded, and he was a lover of  life. Today, although our hearts are aching,   30:13
we need to look up where he is undoubtedly  perched in a crescent moon, and we need to smile. 30:27
Her words cut through the spectacle of the moment.  While the world mourned a global icon, Brook spoke   30:43
about something far more personal. A friendship  rooted in shared experience. Two people shaped by   30:49
the same kind of childhood, navigating fame far  too young, finding brief moments of normality in   30:54
each other. It humanized Michael in a way rarely  seen, not as the superstar, but as the person she   31:00
knew. And when it came time to his memorial, I had  been really out of the public eye with him for a   31:06
dec, you know, decade at least. And it was his mom  who called me and said, "I want you to to speak."   31:15
Because I really thought, "Oh, there, you know,  this is going to be a cartoon. I'm not going to   31:22
I'm not going to be invited. That I never liked  the dad. The dad never liked me." And he's a not   31:27
a human being. He's he's the devil. And you just  look in his eyes and it's just it's a just listen,   31:33
you know, maybe, you know, you kind of look back  and you think, you know, regrets, regrets. I mean,   31:40
his mom is was so lovely and he loved her,  but I do feel like it was unnecessary, unkind,   31:45
and you know, not he wasn't kind. Did you speak  to him at the funeral or No, I did. I had a couple   31:51
cocktails and I went over to him. I don't know  what possessed me. I went over to him and I said,   31:56
"You know what? You never liked me. You never  even pretended to like me. I never liked you.   32:02
You always were mean." And I said, "You know  what? You know what I'm going to tell you?   32:08
I'm going to thank you for your son. I said,  because your son changed the world and was   32:12
my friend. He was just like and he just he tried  to he was gross. He had these young women around   32:18
him. And did Michael hate him? I don't think  you can truly deeply hate your parent because   32:25
you get one of them. I think he was so hurt by  him and I think he just couldn't believe it. He   32:31
couldn't believe how mean he it was to him.  In her 2018 memoir, There Was a Little Girl,   32:38
Brooke would later describe their relationship as  a kind of safe escape. Quote, "Of course, we loved   32:46
each other, but nothing happened romantically.  He was terrified and sort of juvenile. I think   32:52
there was an arrested development." She  wrote, "We just felt safe with each other.   32:58
We watched movies and ate candy and laughed at  the craziness around us. We loved each other,   33:03
but it was not at all romantic. Even years later,  that's how she chose to define it. I like to think   33:09
I was a good friend to him. Our friendship  never altered. It just stayed the course.   33:16
No matter what was happening, whenever we got on  the phone, he would just giggle or laugh and say,   33:21
"Oh, Brooke, I was consistent." And I  think that was important for both of us.   33:27
I've always maintained what a pure soul he was  in the end beyond the headlines, the speculation,   33:31
and the image making. That's what remained. A  friendship, you know, he just he just always   33:38
wanted to be the absolute best best most superior  performer that ever lived. And to my mind, I mean,   33:44
he was the best I ever saw. You know, I don't  think anybody came close. And I think so much was   33:53
imitation. I think he was a one-off for sure. So,  I recently met Paris at the Calvin Klein show. We   33:58
were both reworking with Calvin Kleinhu and she  turned to me and she said, "So, you're my dad's   34:06
friend." And I was so cuz I'd only seen her when  she was a baby and she didn't remember me. And so,   34:13
I said, "Yes, I am." And then I waited a while and  I looked at her and I said, "I really miss your   34:20
dad." And she looked at me and she held me and she  goes, "Me, too." And it was just a pure moment.   34:26
And then we just had a now we have our own kind  of communication together. But she was a she was   34:31
a baby at I mean she was young at the funeral. The  detail is dedicated to uncovering the real stories   34:37
behind Michael Jackson's life and career. If you  enjoy these deep dives, consider subscribing. 34:43

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[English]
Um, hello Brooke. I'm working on my album. Um,  I just want to say hello and I hope I get to see  
you soon. Just a brief message on video. Goodbye.  Michael Jackson once said Brook Shields was one of  
the loves of his life. He told the world they were  dating, that they were in love. But according to  
Brooke, that wasn't true. For years, the two  were photographed side by side. award shows,  
red carpets, private dinners, creating the image  of a Hollywood couple at the height of Jackson's  
fame. But their relationship never quite made  sense. They were always seen together. Yet,  
no one could ever say for certain what they  actually were. They admitted to having feelings  
for each other, but stopped short of defining  it. Two people shaped by fame from childhood  
trying to navigate relationships, identity, and  normality in a world that never allowed it. Were  
they genuine love interests, close friends,  or part of something much more calculated?  
Because the truth is, their relationship  was never what it seemed. Here's the detail.
The very first time the two met was at the 1981  Academy Awards, an event that Michael Jackson  
attended with Diana Ross as his date. Brooke saw  the superstar singer from across the room and  
urged by her mother and manager Terry Shields, who  encouraged Brooke to socialize with celebrities at  
such star-studded events, the 15-year-old boldly  went straight up to Michael and introduced herself  
and asked him if he wanted to dance with her.  Michael Jackson later recalled the encounter.  
Quote, "Before meeting her, her pictures were  all over my walls and mirrors. She just came up  
to me and said, "Hi, I'm Brooke Shields. Are you  going to the afterparty?" I said, "Yeah." And I  
just melted. I was about 23 during Off the Wall.  I thought, "Does she know that photographs of her  
are all over my room?" And we went on the dance  floor. And man, we exchanged numbers and I was  
up all night spinning around in my room just so  happy. From that first meeting, Michael Jackson  
and Brook Shields formed an immediate connection.  What began as a chance encounter quickly turned  
into a close, almost instinctive friendship.  By 1981, both were already global figures.  
But their paths to fame had come at a cost.  Like Michael, Brook Shields had been working  
for most of her life. Thrust into the spotlight as  a child, her early film roles, often provocative  
and controversial, made her one of the most talked  about young stars in the world. At the same time,  
her modeling career exploded. Her Calvin  Klein campaign didn't just make headlines,  
it reshaped the brand entirely, reportedly driving  sales to unprecedented levels. By the early 80s,  
she wasn't just famous. She was a cultural symbol,  even being labeled the face of the decade by Time  
magazine. But behind that image was a reality  that mirrored Michael's in striking ways. Both  
were products of intense parental control. Brook's  career was managed by her mother, Terry Shields,  
a dominant, often overbearing presence whose  struggles with alcoholism added another layer  
of instability. Their relationship was deeply  codependent, blurring the line between protection  
and control. Michael's upbringing followed a  similarly complicated pattern. Driven relentlessly  
by his father, Joe Jackson, he had been pushed  into stardom from a young age. While his mother,  
Catherine, represented a quieter, more protective  force. Someone who wanted a sense of normality for  
her children, even as their lives became anything  but normal. I was 13, I think, when I first met  
him. and we were fans of each others and we just  immediately hit it off. We laughed so hard. I  
didn't I wasn't trying to get a music career. I  wasn't trying to get anything from him and we just  
started hanging out. She would often visit him  unannounced at his family's Havenhurst estate,  
making both his sisters, Latoya and Janet, so  jealous that they tore down Michael's pictures  
of the starlet and called her giraffe butt  behind her back. They found a common bond.  
Michael always felt that unless someone  had sacrificed their childhood for stardom,  
they could never really understand him. That is  why he was so drawn to people like Brooke as well  
as later on with the likes of Elizabeth Taylor and  Macaulay Kulkin, choosing to surround himself with  
former child stars old and new. I think because  we both grew up in this in the same business and  
we had similar upbringings in the sense that we  were you know we we had to begin in this business  
at a very young age. We learned a sense of uh we  had defense mechanisms that we had built up and I  
think once we met each other we realized that we  didn't really have to be wary of one another and  
that just that enabled us to build a friendship on  a very different level. Even though she was only  
a teenager, Brook Shields already embodied the  presence of a classic movie star. She was elegant,  
classy, pure, and well-mannered. All the qualities  that Michael Jackson valued and that he admired in  
other women like his Mottown friend Diana Ross as  well as Princess Diana. In both cases, childhood  
had been sacrificed for success. They weren't  just young stars. They were providers. Both  
carried the weight of expectation, functioning  as the financial backbone of their families  
while navigating an adult world long before  they were ready. And yet, despite everything,  
there was a shared innocence between them. Away  from the cameras and public personas, both Michael  
and Brooke retained a kind of childlike escapism.  They were playful, imaginative, and in many ways,  
still searching for the childhood they never  fully had. With each other, they found a rare  
sense of ease. a space where they could drop the  performance, step outside the pressures of fame,  
and simply exist as themselves. As Michael's  fame reached unprecedented heights following  
the release of Thriller in 1982, Terry  Shields, ever the calculating stage mother,  
recognized the opportunity, aligning Brooke with  the world's biggest star, could only elevate her  
daughter's already rising profile. Therefore,  she encouraged her daughter to make more public  
appearances with the pop superstar, and the  pair became a headline grabbing duo at many  
high-profile events, a carefully managed image  that blurred the line between genuine friendship  
and strategic publicity. Speaking about their  relationship, Michael Jackson recalled that,  
quote, "Broo Shields asked me out every time you  saw us out together. It was her idea to go out and  
do it every time. I sincerely liked Brook Shields,  too. I liked her a lot. Brook Shields was one of  
the loves of my life and we dated a lot. Although  Brooke helped instigate their public appearances,  
the dynamic quickly worked in both their favor.  For Michael, the timing was crucial. After  
Thriller, his fame reached another level. But  so did the scrutiny. Tabloid rumors about his  
personal life, particularly around his sexuality,  were becoming harder to ignore. Being seen  
alongside Brooke Shields, one of the most famous  and desired young women in the world, offered a  
powerful counter image. It reframed how the public  saw him. Brooke, in many ways, was the perfect fit  
for that role. She was already an established  star, but still carried that all-American  
youthful innocence that made the pairing feel  natural and believable. Whether romantic or not,  
it looked right. But beyond the optics, Michael  trusted her. Brooke understood fame. She knew how  
to handle attention, how to protect her image,  and crucially, how to keep things private. For  
someone as guarded as Michael was becoming, that  mattered. He could step out with her knowing she  
wouldn't exploit the moment or get overwhelmed  by the media storm around them. It also gave  
him a sense of support at a time when everything  around him was intensifying. She was a familiar,  
steady presence in very public spaces. There was  also a broader cultural layer as Michael's music  
crossed further into mainstream predominantly  white audiences. Being linked to Brooke subtly  
helped ease that transition. It softened his image  for parts of the public and industry that hadn't  
fully embraced him before. In the end, their  relationship sat in that gray area between genuine  
connection and image making. But at that point  in their careers, it worked for both of them.  
If you wanted to pick up the phone and and call  Michael Jackson, can you can you dial Pluto direct  
or or what's what's the Could you reach him like  other Earthlings couldn't? Yes, I could. Now, let  
me cuz you actually you have been out on several  dates with Mr. Jackson. Is that right? Michael and  
I have been friends for years. And I was like the  the person that he would call because these other  
famous people would sort of really like prey on  him and want to be like I'm going to sleep with  
him because that's going to be a thing. However,  the lines between reality and tabloid fantasy  
would begin to blur. After the 1984 Grammys,  where Michael won a record eight awards, he hosted  
a private party at a downtown restaurant. But  despite the celebrations, he and Brooke slipped  
away early, leaving around 11:30 p.m. Michael  drove Brooke and her mother back to their hotel,  
then went home himself, leaving Brooke  disappointed that he wasn't going to stay the  
night. At the time, they were widely described as  dating, but what actually existed between them was  
far less defined. Over the years, both admitted  there was mutual attraction. Yet, neither ever  
gave a clear answer on whether their relationship  became physical. Perhaps that ambiguity was  
intentional, something that kept them in the  headlines, or maybe it simply reflected their  
own uncertainty. As Brookke said at the time,  quote, "It's hard to say if it's platonic or not.  
We've both had crushes on each other at times.  Despite her public image, Brooke was relatively  
naive when it came to relationships. Her career  had projected a highly sexualized persona from a  
young age. Yet, in reality, she remained cautious  and reserved. Like Michael, many of her closest  
connections began as deep platonic bonds. She  has since explained that her Catholic upbringing,  
combined with the pressures and overexposure  of fame, left her inhibited when it came to  
exploring her sexuality. Michael, meanwhile,  seemed to view her very differently from how  
the public did. While Brooke struggled privately  with body image and her own sense of identity,  
Michael placed her on a pedestal. He reportedly  expressed that he wouldn't want to sleep with  
someone unless he intended to marry them.  In his eyes, Brooke was almost untouchable.  
something pure he didn't want to damage. And yet  there were moments where that boundary nearly  
shifted. Brooke became increasingly curious about  sex. And by her own admission, more interested in  
Michael than she publicly let on, perhaps because  he felt safe, someone who wouldn't push things too  
far. In his autobiography, Moonwalk, Michael  described their relationship as romantically  
serious for a while, later recalling an encounter  where things became more intimate. but he pulled  
back. Quote, "We had one encounter when she got  real intimate and I chickenened out." He said,  
"And I shouldn't have." In many ways, their  relationship remained suspended in that space.  
Somewhere between friendship, attraction, and  something neither of them fully acted on. I mean,  
he's just he's a very soft sort of voice, and he  always says, "Oh, Brooke, I'm so he's always so  
happy to talk to you and he wants to know what  you know what you're doing." And but he's very  
um actually there is no butt. There's just a  a a very genuine innocence that he has that he  
has protected and sheltered himself from so much  that that's been maintained. He has an innocence  
about him that just enables him to revel in in  flowers and children and animals and and he's  
just I mean he talks about his work a little bit  but he really just talks about things that make  
him happy. I mean we we have long discussions  just about everything. So he's quite a regular  
person. He really is. And he's well regular in the  sense that not regular in the sense that he's not  
jaded. Yeah. And I I find that many people in this  business have a tendency it's it's easy to become  
jaded. I mean, people talked about his genius,  but I don't think they talked they didn't really  
know how polarized his sort of life was in so far  as he was extraordinarily a genius and talented  
and he was there was an arrested development I  believe and he was sort of truncated emotionally  
as a little kid and he was a child. He was he  was childlike but but in many ways and we were  
kids together. I think that there was an arrested  development to a certain extent with him in in  
that way but we we act like we acted like little  kids together and I don't think either one of us  
in our lives really had the environment to do that  safely. After the thriller era and the height of  
their public association, both Michael Jackson and  Brook Shields entered a period of transformation,  
each in their own way was trying to take back  control of their life and identity. But the paths  
they chose couldn't have been more different. For  Brooke, it meant stepping away from the industry  
entirely. She enrolled at Princeton University, a  deliberate move to break free from the world she'd  
grown up in and from her mother's control. College  gave her something she'd never really had. Space.  
Space to grow. To form real relationships outside  of Hollywood and to figure out who she was beyond  
the image that had been built around her. For  Michael, independence didn't mean entering the  
real world. It meant creating one of his own. He  began asserting control over every aspect of his  
career, taking charge of his management, building  business ventures, surrounding himself with  
lawyers and trusted collaborators. His ambition  was clear, not just to succeed, but to become  
the biggest star in the world. Where Brooke sought  normality, Michael doubled down on exceptionalism.  
Brooke later recalled how fascinated he was by  her decision to go to college almost in disbelief  
that such a life existed as she began experiencing  relationships and intimacy. She would confide in  
him and his reactions revealed just how sheltered  he'd been. Quote, "He was like a little kid,"  
she said, talking about what first base was, what  second base was. It was a world he simply couldn't  
relate to. as she later reflected, quote, I went  to high school and college and forced that into my  
life. He didn't have that luxury, I think it just  always felt too unattainable for him. By the time  
Brooke graduated in 1987, she had changed. She was  more confident, more grounded, no longer just the  
image the world had projected onto her. She had  experienced real relationships, even losing her  
virginity to her college boyfriend, Dean Kaine.  Michael, however, seemed to remain emotionally  
in the same place. He would occasionally talk  about the idea of them marrying and raising  
children together. But by that point, Brooke saw  things differently. Having experienced genuine  
romantic love, she knew what she wanted and what  this wasn't. She later admitted that marrying  
Michael would have divided her life too much.  She still believed in the idea of a fairy tale,  
but one rooted in real love. And deep down, she  knew Michael wasn't truly in love with her. Quote,  
"There were times when he would ask me to marry  him," she said. "And I'd tell him, "You have me  
for the rest of your life. You don't need to  marry me. I'm going to have my own marriage,  
my own kids, and you'll always have me." In  many ways, their dynamic had shifted. Brooke had  
grown up. Michael hadn't. She moved forward into  adulthood, relationships, independence, reality.  
While Michael remained suspended in a world of  his own making, still chasing something just out  
of reach. Like Wendy leaving Neverland while Peter  Pan stayed behind. I mean, I remember saying this  
to him. He He couldn't believe I was going to go  to schools. He couldn't believe I was going to go  
to regular schools, that I was going to go away  to college by myself, that I was going to then  
when I told him I was getting married, he was he  just didn't get it. He was like, "You what? You  
can't do that." And I said, "I've got a chance."  I said, "I've been going out in the world. I'm not  
so isolated, and I want I want this chance.  I want a chance to be quote unquote normal,  
you know, and it and he never really could trust  a lot of people around him." Despite the shift  
in their dynamic, Michael and Brooke remained  close in the years that followed. In 1991, Brooke  
attended Elizabeth Taylor's seventh wedding as  Michael's date held at his Neverland Ranch estate.  
Around the same time, Slash recalled being  introduced to Brooke by Michael as his girlfriend  
before Jackson left them in the studio to take her  out to dinner. Their outings became something of a  
spectacle. As Brooke later put it, quote, "We used  to go out to restaurants. It was madness. Getting  
in and out was chaos, but once we were inside,  we could just sit and be normal for a moment."  
That balance between chaos and normality defined  their public relationship, but there was also  
a growing sense that the attention wasn't  entirely accidental. In later interviews,  
Brooke suggested that Michael may have tipped  off photographers, aware of the publicity their  
appearances together would generate, and at  that stage in her career, that visibility  
wasn't unwelcome. After graduating, Brooke had  struggled to reestablish herself in Hollywood.  
Casting opportunities were limited and the  industry didn't quite know where to place  
her anymore. Being seen alongside Michael, still  one of the most photographed people in the world,  
kept her in the headlines and crucially kept her  relevant. Together, they leaned back into the  
image they had once created, playing their roles  in front of the cameras, even as the nature of  
their relationship had changed. But as the years  went on, the tone around Michael began to shift.  
Media scrutiny intensified, becoming more invasive  and at times openly critical. And increasingly,  
Brooke found herself being asked to speak on his  behalf. Put in a position where she felt she had  
to defend him not just as a public figure, but  as a friend. When you're in his presence, and I  
don't mean this tongue and cheek at all, is there  something eerie about him? No, it's not eerie in  
the sense of uh scary or weird. He's so creative.  I mean he's he borders on genius. And I think that  
when you are you have that much talent and you  are at the same time that sensitive of a person,  
you your conversation is going to be different  with him. And I think that that's where one  
might interpret it as eerie. It's not. It's not  though. and all it takes is a joke or laughing  
or talking to him or you know saying look I'm I'm  here too and you're hearing do the uh unfortunate  
nasty comments and criticisms about him do they  upset you make you they upset me constantly I'm  
constantly upset by what people say I mean first  of all people so many people really don't know  
him and they don't give him a chance and they're  so ready to criticize and I think what happens is  
when you see genius and when you see a talent that  is just unstoppable and untouchable. The first  
reaction people have is to criticize it because it  scares them. It threatens them and it sort of it  
um in order to augment their own selfworth, they  feel that they have to belittle him. And you know,  
he's a sensitive human being who this this all  of the negativity really it does affect him and  
it hurts him. How how do you recognize him between  dates? How do you know it's him coming up? because  
he does look very different now, don't he? He He  does look different. We We don't ever discuss any  
of that actually. We talk a lot on the phone, so  it's usually his voice that gives him away. But do  
you do you find yourself biting your lips saying,  "The man has a completely different nose." And  
then you go, "What a terrific weather we've been  having, Michael." How do you avoid the issue? We  
It's It's not something that you just really want  to ever talk about or dwell on. But we actually  
for the wedding we were um I mean it was really  interesting because I was there from the Oh,  
so we're back to the wedding now. So yeah, light  segue. Yeah. Um yeah, the wedding. How big is  
Michael Jackson's willing? I think you should ask  Michael Jackson. That's my thing I'll never find  
out. However, while Brooke had always been careful  to keep their relationship private, Michael  
appeared to cross that line himself during his  1993 sit-down interview with Oprah Winfrey. When  
asked about his personal life, Michael claimed  he was dating and in love with Brooke Shields,  
adding that they kept things out of the public eye  to maintain privacy. Do you go out? Do you date?  
Yes. Who do you date? Well, right now it's Brooks  Shields. Mhm. That's I don't Well, we try not to  
just be everywhere and go every It's mostly at  home. She'll come over. I'll go to her house cuz I  
don't like going out in the public. Have you ever  been in love? Yeah. Mhm. With Brook Shields? Yes.  
And another girl. And another girl. The problem  was Brooke was in no way dating him at the time.  
She was in a relationship with her future husband,  Andre Agassi. According to later accounts,  
after watching the interview, she called Michael  and demanded to know what he was doing. From  
her perspective, the line between suggestion and  reality had been pushed too far. On the surface,  
it looked like a clear fabrication, a calculated  move to soften Michael's image and steer attention  
away from growing scrutiny. But the situation  wasn't entirely one-sided. Earlier that same day,  
Brooke had appeared on Oprah's show herself and  notably didn't shut down any romance speculation.  
Instead, she hovered in that familiar gray  area, neither confirming nor denying anything,  
allowing the idea of them as a couple to linger  in the public imagination. I want to know what  
the real deal is, Brooke, between the two of you.  Was there was there romance going on? Were you all  
kind of romantically involved? Was there like ever  an exchange of, you know, rings or anything or  
um Well, actually, I think right now, let me say  that I believe that we're closer now than we ever  
were. I think we love each other more now than we  even knew we did when we were younger. Really? We  
We used to Well, because we had fun when we  were younger. I mean, it was And we were sort  
of a source of relief. This is a question. Did you  have a crush on him or did he have a crush on you?  
I think we both had a crush and still do have  a crush on each other. I mean, I think part of  
having a crush on someone is admiring them almost.  I mean, you have we have a lot of fun together. I  
mean, it's almost unfortunate cuz we know each  other so well. But, I mean, he just he amazes  
me every time I sit down and talk to him about  something really. Does he feel does he feel more  
like a brother to you though than say a boyfriend  though? It's hard to say. I mean, I I find it's a  
love on a different level. I mean, I feel closer  to him than the some of the boyfriends that  
I've had. It was a pattern they had fallen into  before. Whether it was a quiet favor to Michael,  
helping reinforce a more conventional  image, or something that also served Brooke,  
who at the time was struggling to regain momentum  in her acting career. Brooke had always preferred  
to keep things deliberately vague. So when Michael  suddenly went public claiming they were dating and  
in love on one of the most watched interviews  ever, it crossed a line she hadn't agreed to.  
Therefore, she firmly denied the claim in the  press. The confession didn't appear to damage  
their relationship as just weeks later, Brooke  accompanied Michael to the 1993 Grammys where he  
received the Grammy Legend Award from his sister  Janet Jackson. It felt almost nostalgic, echoing  
their appearance together nearly a decade earlier.  Around this time, Michael also gave Brooke a ring.  
She later recalled how he casually threw the  box towards her. Inside was a large diamond  
encrusted ring. Unsure how to interpret it, she  asked what it meant. Michael simply told her,  
"I just want to show that I love you and that  I care for you." For him, it was a gesture of  
affection. For Brooke, it was something harder  to define, much like their relationship itself.
However, just months later, Michael Jackson  found himself at the center of a media storm  
following allegations made by a 13-year-old  boy. Jackson faced intense public scrutiny. The  
press coverage was relentless. Sponsors began to  distance themselves, and his commercial momentum  
started to falter. Behind the scenes, there was  growing pressure to repair his image and fast. One  
widely discussed strategy was simple marriage. The  thinking was that presenting a more conventional  
heterosexual image could help counter the  narrative forming around him. During this period,  
Michael reportedly made a serious proposal  to Brooke, the woman he'd been most closely  
linked to for over a decade, a familiar figure  who had helped steady his image during periods  
of speculation. But by then that dynamic was gone.  Brooke was in her late 20s in a relationship with  
Andre Agassi, someone she was genuinely in love  with. And she had begun to distance herself from  
the Hollywood world she'd grown up in. She wanted  something more grounded, more private, and she  
understood the weight of what Michael was facing.  Even before the allegations, his life came with  
a level of scrutiny she no longer wanted to be  part of. So she said no. It was a turning point.  
Shortly after, Michael turned his attention  elsewhere, proposing instead to Lisa Marie  
Presley, who accepted. Their marriage, announced  in 1994, would become one of the most talked  
about and scrutinized relationships of the  decade. When asked about Michael Jackson's  
marriage to Lisa Marie, Brooks stated, quote,  I think we're not dealing with convention. So,  
somebody like Michael, he's not going to just  fall in love with somebody and get married.  
I think there were a few people that he could  identify with. And what I know about Lisa Marie,  
she was very sweet. She could identify with him.  They could talk about things that I'm sure she  
understood with regards to her father. Brook's  rejection of Michael's proposal effectively ended  
the public dynamic they had built together.  From that point on, the two gradually lost  
touch. Life moved on. Brooke remarried in 2001 and  started a family. But behind the scenes, she was  
struggling. After the birth of her first child,  she experienced severe postpartum depression. When  
she spoke publicly about it, Michael reached  out, sending flowers. Despite the distance,  
there was still a thread connecting them. Quote,  "At every major event in my life, he reached out."  
She later said, "When my dad died, when I had  my first daughter, we'd speak. But over time,  
it became harder to reach him. the people around  him changed and in the last few years it was  
difficult to even get through to him. Her concern  for him never really went away. Quote, "I was  
worried about him financially. I was worried about  the kids. I was worried about his health. I always  
worried about his health because I thought he was  just too skinny." Even as their lives diverged,  
there was still a sense of care, a quiet,  lingering connection that never fully disappeared.  
Did you remain friends throughout? Throughout. He  was the first person to call me when my dad got  
sick. Wow. He, you know, when I had postpartum,  he, you know, he sent me flowers and, you know,  
all of these things even though we sort of  hadn't had our regular dinners that we used  
to have on a more regular basis. Um, but he was  the he was consistent. By the time of Michael  
Jackson's death in 2009, the two hadn't been seen  together publicly for over 16 years. And yet,  
the connection clearly remained. At the request  of Michael's mother, Catherine Jackson, Brooke  
was asked to speak at his public memorial at the  Staples Center in Los Angeles. What followed was  
one of the most emotional and memorable moments  of the service. Reflecting on their relationship,  
she said, quote, "Whenever we were out together,  the caption usually said something like, "An odd  
couple or an unlikely pair." But to us, it was the  most natural and easiest of friendships. Michael  
always knew he could count on me to support him or  be his date, and that we would have fun no matter  
where we were. We had a bond. Both of us needed to  be adults very early, but when we were together,  
we were two little kids having fun. To the outside  world, Michael was a genius with unchallenged  
ability. To the people who were lucky enough to  know him personally, he was caring and funny,  
honest, pure, non-jaded, and he was a lover of  life. Today, although our hearts are aching,  
we need to look up where he is undoubtedly  perched in a crescent moon, and we need to smile.
Her words cut through the spectacle of the moment.  While the world mourned a global icon, Brook spoke  
about something far more personal. A friendship  rooted in shared experience. Two people shaped by  
the same kind of childhood, navigating fame far  too young, finding brief moments of normality in  
each other. It humanized Michael in a way rarely  seen, not as the superstar, but as the person she  
knew. And when it came time to his memorial, I had  been really out of the public eye with him for a  
dec, you know, decade at least. And it was his mom  who called me and said, "I want you to to speak."  
Because I really thought, "Oh, there, you know,  this is going to be a cartoon. I'm not going to  
I'm not going to be invited. That I never liked  the dad. The dad never liked me." And he's a not  
a human being. He's he's the devil. And you just  look in his eyes and it's just it's a just listen,  
you know, maybe, you know, you kind of look back  and you think, you know, regrets, regrets. I mean,  
his mom is was so lovely and he loved her,  but I do feel like it was unnecessary, unkind,  
and you know, not he wasn't kind. Did you speak  to him at the funeral or No, I did. I had a couple  
cocktails and I went over to him. I don't know  what possessed me. I went over to him and I said,  
"You know what? You never liked me. You never  even pretended to like me. I never liked you.  
You always were mean." And I said, "You know  what? You know what I'm going to tell you?  
I'm going to thank you for your son. I said,  because your son changed the world and was  
my friend. He was just like and he just he tried  to he was gross. He had these young women around  
him. And did Michael hate him? I don't think  you can truly deeply hate your parent because  
you get one of them. I think he was so hurt by  him and I think he just couldn't believe it. He  
couldn't believe how mean he it was to him.  In her 2018 memoir, There Was a Little Girl,  
Brooke would later describe their relationship as  a kind of safe escape. Quote, "Of course, we loved  
each other, but nothing happened romantically.  He was terrified and sort of juvenile. I think  
there was an arrested development." She  wrote, "We just felt safe with each other.  
We watched movies and ate candy and laughed at  the craziness around us. We loved each other,  
but it was not at all romantic. Even years later,  that's how she chose to define it. I like to think  
I was a good friend to him. Our friendship  never altered. It just stayed the course.  
No matter what was happening, whenever we got on  the phone, he would just giggle or laugh and say,  
"Oh, Brooke, I was consistent." And I  think that was important for both of us.  
I've always maintained what a pure soul he was  in the end beyond the headlines, the speculation,  
and the image making. That's what remained. A  friendship, you know, he just he just always  
wanted to be the absolute best best most superior  performer that ever lived. And to my mind, I mean,  
he was the best I ever saw. You know, I don't  think anybody came close. And I think so much was  
imitation. I think he was a one-off for sure. So,  I recently met Paris at the Calvin Klein show. We  
were both reworking with Calvin Kleinhu and she  turned to me and she said, "So, you're my dad's  
friend." And I was so cuz I'd only seen her when  she was a baby and she didn't remember me. And so,  
I said, "Yes, I am." And then I waited a while and  I looked at her and I said, "I really miss your  
dad." And she looked at me and she held me and she  goes, "Me, too." And it was just a pure moment.  
And then we just had a now we have our own kind  of communication together. But she was a she was  
a baby at I mean she was young at the funeral. The  detail is dedicated to uncovering the real stories  
behind Michael Jackson's life and career. If you  enjoy these deep dives, consider subscribing.

Key Vocabulary

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Vocabulary Meanings

celebrity

/səˈlɛbrɪti/

B2
  • noun
  • - a famous person

provocative

/prəˈvɒkətɪv/

C1
  • adjective
  • - causing annoyance, anger, or another strong reaction

controversial

/ˌkɒntrəˈvɜːʃl/

B2
  • adjective
  • - giving rise or likely to give rise to public disagreement

instability

/ˌɪnstəˈbɪləti/

C1
  • noun
  • - the state of being unstable

codependent

/ˌkəʊdɪˈpendənt/

C2
  • adjective
  • - excessively dependent on a partner

navigate

/ˈnævɪɡeɪt/

B2
  • verb
  • - to find one's way through a situation

scrutiny

/ˈskruːtəni/

C1
  • noun
  • - critical observation or examination

innocence

/ˈɪnəsns/

B2
  • noun
  • - lack of guilt or worldly experience

tabloid

/ˈtæblɔɪd/

B2
  • noun
  • - a newspaper with small pages and popular style

ambiguity

/ˌæmbɪˈɡjuːəti/

C1
  • noun
  • - the quality of being open to more than one interpretation

platonic

/pləˈtɒnɪk/

C1
  • adjective
  • - intimate and affectionate but not sexual

pedestal

/ˈpedɪstl/

C1
  • noun
  • - a base or support on which something stands

jaded

/ˈdʒeɪdɪd/

C2
  • adjective
  • - tired, bored, or lacking enthusiasm

polarized

/ˈpəʊləraɪzd/

C1
  • adjective
  • - divided into two sharply contrasting groups

unattainable

/ˌʌnəˈteɪnəbl/

C1
  • adjective
  • - not able to be reached or achieved

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Key Grammar Structures

  • Michael Jackson once said Brooke Shields was one of the loves of his life.

    ➔ Past Perfect (implied) / Reported Speech

    ➔ The speaker uses 'said' followed by a clause to report past statements.

  • For years, the two were photographed side by side.

    ➔ Passive Voice

    ➔ The focus is on the subjects ('the two') receiving the action of being photographed.

  • Like Michael, Brooke Shields had been working for most of her life.

    ➔ Past Perfect Continuous

    ➔ Used to describe an action that started in the past and continued up until another point in the past.

  • I wasn't trying to get a music career.

    ➔ Past Continuous (Negative)

    ➔ Expresses an ongoing action in the past that was not happening.

  • He's just he's a very soft sort of voice.

    ➔ Determiner / Quantifier (sort of)

    ➔ 'Sort of' is used here to hedge or soften the description.

  • If you wanted to pick up the phone, could you reach him?

    ➔ Second Conditional

    ➔ Used to talk about hypothetical or imaginary situations in the present/future.

  • I would chicken out.

    ➔ Modal Verb (would + phrasal verb)

    ➔ 'Would' indicates a habitual past action or a result of a condition.

  • I've been going out in the world.

    ➔ Present Perfect Continuous

    ➔ Describes an action that started in the past and is still continuing or just finished with a focus on the activity.

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