By Meredith Vieira
Dateline NBC
updated 9/25/2009 8:23:34 PM ET 2009-09-26T00:23:34
transcript

This aired on Dateline NBC on Friday, Sept. 25. The full hour will be not be available online, but you can watch web-exclusive related video here.

His voice is instantly familiar:

Michael Jackson: I wanted to become such a wonderful performer that I would get loved back.

... But his words are so haunting.

Michael Jackson: If it weren't for children, I would choose death.

Words of pain and torment.

Michael Jackson: Anybody else would probably be dead by now, or a junkie, with what I've been through.

Bitterness and rivalry.

Rabbi Shmuley:  What about jealousy from other stars and things like that? Is there a lot of jealousy?

Michael Jackson

:  Absolutely ... and "M" is one of em. Madonna. Hate to say that on tape. Video: Michael Jackson’s feelings toward women

And a legendary star's deepest fears.

Rabbi Shmuley: Do you want to have a long life?

Michael Jackson:  I think growing old is the ugliest, the most, the ugliest thing.

RabbiShmuley: I don't think that Michael Jackson will ever be looked at the same after this book. It's impossible. There's just too much rawness and honesty of Michael in this book for anyone to ever perceive him as the same.

Now, for the first time, spilling out across page, and on tape: Michael Jackson in his own words. Up until now, these recordings have never been released.

They're being played exclusively on NBC, along with the release of a new book:  The Michael Jackson Tapes: A Tragic Icon Reveals His Soul In Intimate Conversation.

Author Rabbi Shmuley Boteach -- a relationship expert who calls himself "America's Rabbi" -- calls it "The King Of Pop Raw," exposed like never before.

RabbiShmuley: You could see that there was a woundednessto him, he wasn't very trusting, he opened up very slowly.

Meredith Vieira, NBC News: But one of the first questions that people might ask is "did you betray his confidence in any way by releasing these tapes now, after his death?"

RabbiShmuley:  Not only have I not betrayed any confidences, Michael used to hold the tape recorders directly to his mouth. He would constantly talk to me about the book. “Make sure this is in the book." He desperately wanted this out.

He counted mega-celebrities like Diana Ross and Elizabeth Taylor among his closest friends. But this is Michael Jackson bluntly dissing Hollywood.

RabbiShmuley: Why don't you hang out with those celebrities, more Hollywood people?

Michael Jackson:  They love the limelight and I don't have anything in common with them. They want to go clubbing and afterwards they want to sit around and drink hard liquor and do marijuana and all kinds of crazy things that I wouldn't do.

And forget the mask, the chimp, the baby dangling, and any other eccentric behavior we already know about. Here, Jackson talks openly about his oddest -- and saddest -- habits. Video: Jackson’s ‘celebrity was so isolating’

Michael Jackson:  I needed someone. That's probably why I had, uh, the mannequins, I would say.  Because I felt I needed people, someone, and I didn't have, I was too shy to be around real people. I love them, it's like real babies, and kids, and people, but it makes me feel like I am in a room with people.

Rabbi Shmuley first met Michael Jackson in 1999, and began recording their conversations a year later, when Jackson was 42 years old. Theirs was an unlikely friendship -- but the Orthodox rabbi had became a confidant and spiritual advisor to the King Of Pop.

RabbiShmuley: As we got to know each other more, I think he began to believe that I got him.

MeredithVieira: Did he see in you then, Rabbi, the opportunity to be a regular guy?

RabbiShmuley: So many of us look at Michael as strange and weird, that's not what I experienced. He never wore a mask in my presence. The kids were never veiled in my presence. Michael wasn't a celebrity for me anymore.

MeredithVieira: What did you see?

RabbiShmuley: Indescribable pain. Tremendous remorse and regret.

Shmuley says Jackson, who was still reeling from 1993 sexual abuse allegations, wanted the public to hear his voice.

MeredithVieira: The plan was always to publish the conversations?

RabbiShmuley: Absolutely.

MeredithVieira: But why did he want that out there? Why did he want a book of the conversations?

RabbiShmuley: He knew that the public was deeply suspicious of him. I think he wanted be known as a man without a mask.

During the nine-month period when the tapes were made, the rabbi says he and Jackson were so close, he considered him part of the family.

Shmuley's children still have Marshmallow, the dog Jackson gave them, along with fond memories of the many Friday nights when the King Of Pop joined them in Englewood, New Jersey for Sabbath dinner.

RabbiShmuley: He used to tell me they were the most special evenings of his life.  He would arrive with Prince and Paris, very often his-- security detail would join us. And we would just sit around and Michael would just laugh and giggle.

Prince and Paris, who were toddlers at the time, were often in tow when the tape recorders were rolling too -- sometimes jumping right into the conversation.

Rabbi Shmuley: How old were you now?

Prince (in background):  We're three!   (laughter)

If the world sees him as the strange father who cloaked his children in masks, the tapes reveal the tender dad we didn't see.

Michael Jackson: Like I say to Prince and Paris, "You know why I bought you this?"  They say "because you love me." I say "yes, that's why I bought it."  They need to know that.

The rabbi says family bonding was such a central part of his friendship with Jackson that they began working on a national campaign to promote Friday nights as family night.

Rabbi Shmuley: A national family dinner time. Because families who eat with their children, it minimizes drug use, early sexuality, there are so many benefits.

It's a dream rooted in Jackson's own childhood scars.

Michael Jackson: If I had, if there were a children's day when I was little, and I looked at my father and say "OK, Daddy, Joseph,-what are we going to do today?", you know what that would've meant to me? He go "Well, want to go to the movies?" That would've meant so much to me, Shmuley.  (tearing up)

With his tears sometimes audible, the Michael Jackson you'll hear now comes out from behind his mask, unveiling a man few people knew –or could ever comprehend.

Michael Jackson: And I'm -- I'm going to say something I've never said it before, uh, um, and this is the truth, Shmuley.  I-- I have no reason to lie to you. God knows I'm telling the truth. I think all my success and fame --and I've wanted it. I've wanted it. Because I wanted to be loved. That's all.

As the lead singer of the Jackson 5, Michael Jackson was a childhood sensation. But behind his beaming smile, there was searing pain.

Michael Jackson: It's true, Shmuley. I suffered a lot in that way.

Rabbi Shmuley: Michael had a broken childhood. There were always two Michael Jacksons. There was Michael Jackson, African-American boy from Gary, Indiana, who grew up in abject poverty. And then, there was the King Of Pop.

Jackson, the King Of Pop, has talked about Michael, the boy, before ... But never like this.  In unsettling detail, he opens up about his fear of his father and manager, Joe Jackson.

Michael Jackson: You'd look in the audience, and he'd make a face like this. You'd go,"I can't mess up, he's gonna kill us.” It would scare the bejesus out of you and you'd be like, everybody's clapping and he'd be like, like looking at you hard, like "Don't you mess up" and you know, I'm like, "Oh God, I'm in trouble after the show." 

RabbiShmuley: There was no one on Michael's mind more than his father Joseph, no one. His father came up constantly, usually in painful, negative stories.

Jackson told Shmuley that growing up, he and his siblings would dread the moment their father came home.

Michael Jackson: We'd hear his car comin' the driveway. He always drove a big Mercedes and he drives real slow.  "Joseph's home, Joseph's home, quick!"  Doors slam, everybody runs to their room.

Like there's sometimes I'd be in bed at night sleeping, it's 12 at night. The door is locked.  He said, "I'm giving you five seconds, you don't open, I'm going to kick it down."  And he starts kicking it, boom!  Like breaking the door down. Why didn't you sign that contract today?  I go, "I don't know."  He goes, "Well, sign it.  If you don't sign it, you are in trouble."

Rabbi Shmuley: So you would sign?

Michael Jackson:  I had to!  He would, he was very physical.  He'd throw you and hit you as hard as he can.

And as Michael describes to the rabbi, they were beatings that sometimes got brutal.

Michael Jackson: He was rough. The way he would beat you, you know, was hard, you know. Sometime he take, um, he would make you strip nude first. He would oil you down. It would be a whole ritual. He would oil you down so when the flip of the ironing cord hit you, you know. And it would just like be dying and you had whips all over your face, your back, everywhere. And I always hear my mother, "No, Joe! You're gonna kill 'em. You're gonna kill 'em, no!" I would just give up, like there was nothing I could do, you know? And I, and I hated him for it, hated him.

Rabbi Shmuley:  Michael was terrified of his father.

Terrified, and also resentful.

Rabbi Shmuley:  Did you begin to feel that you were like a moneymaking machine for him?

Michael Jackson: Yes. I'll never forget it, one day he said, "If you guys ever stop singing, I'll drop you like a hot potato."  That's what he said. It hurt me. You don't say that to children and I never forgot it.

It was a shunning of affection that colored almost all Jackson's childhood memories of his father.

Michael Jackson: I never felt love from him. And he would never hold me or touch me.

Rabbi Shmuley:  He only has one memory of his father ever doing anything loving for him as a child. He was about 5 years old. He was at a carnival. And his father picked him up and put him on a horse. And he said he has relived that moment almost every day of his life. Michael learned the devastating effects of neglecting a child.

Jackson told Shmuley his sadness created a torment so wrenching that he and his siblings even fantasized about their father being dead.

Michael Jackson: We used to say to our mother, we used to say to each other, and I'll never forget this. Janet and myself, we say, I would say, "Janet, shut your eyes." She'd go, "Okay, they're shut." I'd say, "Picture Joseph in a coffin. He's dead. Did you feel sorry?" She'd go, "No." That's what we used to do to each other as kids. We'd like play games like that. She'd go, she'd go, "Nope." Just like that. And that's how hateful we were.

Jackson's siblings have said in the past that Joe Jackson was hard on them, but their descriptions are inconsistent. And Joe Jackson has said he whipped his son, but never beat him. A spokesman for the Jackson family told us "The family will not dignify this with a comment."

Meredith Vieira: You've met Joe Jackson.

Rabbi Shmuley: I have.

Meredith Vieira: Does this ring true to you, does it make sense to you?

Rabbi Shmuley: What's not important, as far as Michael is concerned, is whether or not these allegations are true, they may not be true, but Michael certainly perceived them to be true.

And like most things in Jackson's life, nothing was black and white. At times, he spoke fondly of his father -- crediting him with much of his own success.

Michael Jackson: And God bless my father because he did some wonderful things, and he was brilliant, he was a genius.

Meredith Vieira: He always talks about how brilliant his dad was.

Rabbi Shmuley: Michael was wrestling with his anger and his disappointment.

Rabbi Shmuley:  And how do you view him today?

Michael Jackson: I'm scared of my father to this day. My father walk in the room -- and God knows I'm telling the truth. I've fainted in his presence many times. I'll say once, to be honest. I fainted once.  I've thrown up in his presence because just when he comes in the room, ugh, this aura comes and my stomach start hurting and I know like I'm in trouble.  And now, he's so different now. And he wants to be a better father. I just wished he had of learned that earlier.

Rabbi Shmuley: Why are you still scared then?

Michael Jackson:  Because the scar is still there. I'm like an angel in front of him, I'm scared.  One day he said "Why are you scared of me?"  And I couldn't answer.  I thought, I said, “Joseph, do you know what you've done?  Do you know what you've done to me?"

Rabbi Shmuley: I think that it was Michael's inability to be reconciled with his father that ultimately, more than anything else, consumed him.

Meredith Vieira: Because?

Rabbi Shmuley: Because he wanted his father's validation and love more than anything else.

Meredith Vieira: And when he didn't get it?

Rabbi Shmuley: He couldn't heal.  Millions of fans couldn't heal him.

He may well have been the most famous celebrity of all time -- imitated, adored, and revered by fans around the world. But Michael Jackson's conversations with Rabbi Shmuley reveal a man that almost no-one knew, so wounded by his father's neglect that all he ached for was love.

Michael Jackson: I wanted to become such a wonderful performer that I would get loved back.

Rabbi Shmuley: You thought if you became a great star, very successful and loved by the world, your father would love you too?

Michael Jackson: Mmhmm.

Rabbi Shmuley: So you could change him that way.

Michael Jackson: Mmhmm.  I was hoping I could, I was hoping I could get love from other people.  I needed it, real bad, you know?

Rabbi Shmuley: A guy whose career was world famous and now he's saying "It wasn't ‘cause I love music, it wasn't because I love dancing." It was because I'm so lonely.

Meredith Vieira: Rabbi, how did you come to the conclusion that he wasn't sort of, you know, making up excuses for you too?  "Oh, I'm this way because my father was mean to me"?

Rabbi Shmuley: You can't fake sincerity. He cried through much of these tapes. He was just gasping for breath at times. I mean, this was a confessional that he had never really undergone.

With surprising honesty -- as you've never heard him before -- Michael Jackson talks candidly about race. He believes his broad appeal to white fans made him suffer more than any famous black star before him.

Michael Jackson: You had Belafonte, you had Sammy, you had Nat King Cole. People loved their music, but they didn't get adulation, they didn't get crying. I was the first one to break the ice, break the mold, where white girls, Scottish girls, Irish girls screaming, "I'm in love with you, I want to -" And that gave a lot of the white press, they didn't like that, and that's why they started the stories.  "He's weird."  "He's gay."  "He sleeps in a hyperbaric chamber."  "He wants to buy the Elephant Man bones" -- anything that turn people against me. They tried their hardest.

In addition to accusing the press of racism, Jackson divulges painful stories about the ugly overtones of race that hovered over his family, long after he became a superstar.

Michael Jackson: My mother - she was pulling out of the market, right, it was a block from my house in Encino and she was in her Mercedes. And this white guy in a car screams out to her, "Go back to Africa, you n***ger."  Just like that.  It hurt me so much that that happened to be mother. Or stories of my brothers in their Rolls-Royces, you know, get out of the car, lock the door, when they come back to the car they would find a key, some guy walked by and scrape off all the paint.

Shmuley Boteach: 'Cause it was a black man driving it?

Michael Jackson: A black man driving a Rolls Royce, you know. I just hate anything to do with because the color of a person's skin had nothing to do with the content of their character.

And despite being one of the most influential entertainers of all time, Jackson says he never understood why he still couldn't catch a break from the press, even when he wrote ballads like "earth song" and focused on making the world a better place.

Michael Jackson: I've been an ambassador of goodwill all over the world, spreading this message, did we do heal the world, treaty of all nations, circling this huge globe? What I don't understand is just singing about sex and "I want to get in a hot tub with you baby and rub you all over" and, but I get battered in the press as the weirdo.

Michael Jackson: And the press, they wait--wait with knives, really...

Shmuley Boteach: For you to fail?

Michael Jackson: Absolutely.  They try and shred me apart. Because when you are the top-selling artist of all time, the records that are broken, they wait. You're the target now.  Get him down, get him, you know what I mean?

As he opened up to the rabbi, Jackson could sound narcissistic.

Michael Jackson: Going to my shows, it's like a religious experience, because you come out, you go in one person, you come out a different person.

But more often, he sounds anguished and sad. The star who spent his adult life morphing from one look to another, actually admits his own face repulses him.

Michael Jackson: I saw it on the computer, it made me sick when I saw it.

Rabbi Shmuley: Why?

Michael Jackson: I look like a lizard, I look like, it's horrible. I don't like it, I never like it.  That's why I wish I could never be photographed or seen and I push myself to go to the things that we go to. 

Michael Jackson: I just don't want to look old. I hate to see people grow old, Shmuley.

Meredith Vieira: He didn't want to see himself in the mirror with wrinkles. He had a whole thing about getting older. Did he ever talk to you about plastic surgery?

Rabbi Shmuley: I used to always tell him that he had to stop. He swore to me he did. But he didn't.

Jackson also shared with the rabbi some disturbing details about his eating habits --  confessing that on his dangerous tour, his friend Elizabeth Taylor literally had to force him to eat.

Michael Jackson: I wouldn't eat. She took the spoon and would put it into my mouth.

Rabbi Shmuley: Really?

Michael Jackson: When I get really upset or hurt, I don't eat. I go on a food, I just get - until I'm unconscious. Then they started doing it intravenously, you know, because I just, my body breaks down, I won't eat.

And then there were the drugs.  Although Shmuley says he never saw Jackson actually taking them, he did tell the star he was concerned -- especially after one doctor complained that Jackson had asked for a dose of drugs that could kill a horse.

Rabbi Shmuley: He medicated away all his problems. When a man is slowly making his body into a walking pharmacy, it was so obvious: Michael's drugs were primarily an escape from loneliness

Even back in 2001, Michael Jackson seemed to be drowning in an ocean of despair. In fact, the only thing that seemed to keep him going was his love for children.

Rabbi Shmuley: So what gave you the strength to persevere?

Michael Jackson:  Believing in children.  Believing in young people. Believing that God gave me this for a reason, to help my babies.

Little did he know how soon that belief -- and one child in particular -- would lead to accusations that this time  would forever tarnish his career.

If Michael Jackson was a man who never had a childhood, he seemed to spend most of his adulthood chasing it. If he could, he told the rabbi, he would stay a child forever.

Michael Jackson: I would love to come back as as a child that never grows old, like Peter Pan.

In fact, even at age 27, when “Thriller” was topping the charts, the King Of Pop was still living at home with Mom and Dad.

Michael Jackson: I thought I was still this little kid.  It's not time for me to go yet.  I said I'm still a boy.  I'm not supposed to leave home yet.  I really felt that in my heart.

And when he did finally move out, Michael Jackson remained as childlike as ever -- famously naming his ranch "Neverland"  -- a place where he surrounded himself with laughing children, and relished playing games like hide-and-go seek.

Michael Jackson: I see beauty in all children. They all beautiful to me.  They're so beautiful and I love them all -- equally.

Rabbi Shmuley: He wanted to have an ordinary life. But for him, ordinary meant reversing to his childhood.  That if he could just build Neverland and have rides, which he didn't have when he was a kid.  If he could just have monkey bars and merry-go-rounds, which he didn't have when he was a kid, that he would heal.

But Neverland was a place where innocence and darkness would collide as the real motives behind the King Of Pop's connection to children raised unsettling questions.

Rabbi Shmuley: He didn't like talking about that. That was very painful for him. To the extent that he talked about it, he would say that it was a lie-- it was a lie.

What Jackson does talk openly about on tape -- at great length - is his deep empathy for children, telling the rabbi he can't bear to see them suffer.

Michael Jackson: It can be in a movie or I could be in a department store and I'll hear someone arguing at their child, I break down and cry.  Because it reflects how I was treated when I was little.  I cry -- I break down at that moment and I shake and I cry.  I can't take it.  It's hard.

Jackson didn't just love children, he told the rabbi. He needed them -- they were his refuge, his saviors.

Michael Jackson: The happiness and the joy that I see in the eyes of the children.  They give me-- they saved my life so I want to, give it back [starts crying]. They saved me, Shmuley.  I'm not joking.

Meredith Vieira: He says children have literally saved his life.  What did he mean?

Rabbi Shmuley: That it's the only thing left he has to live for.  He had achieved all his dreams.  He'd become a billionaire, but that didn't make him happy.  He had become the most recognizable face on earth, arguably, but that didn't make him happy.  The only thing that did was to learn from the pain of his absent childhood, to teach others that children are precious.  And that gave him purpose. 

But it was a mission Jackson seemed to take to an extreme -- even telling the rabbi he sees himself as a universal father who has the power to heal sick children.

Rabbi Shmuley:  Do you feel that God gave you a certain healing power?

Michael Jackson: Yes. And I've seen children just shower all over me with love.  They want to just touch me and hug me and completely just hold on and cry and not let go. And mothers pick their babies and put them into my arms.  "Touch my baby, and hold them, touch my baby, touch my baby." 

Meredith Vieira: He did see himself as somewhat of a Messiah, with healing powers

RabbiShmuley: He would say to me, "I want to devote my whole life to helping kids, that's the only thing that's important to me." And I would say, "You can help kids. But you're not their parent. Stop believing you're the child's Messiah."

In august of 2000, Jackson invited Rabbi Shmuley and his family to Neverland. At the very same time, a young boy, a 13-year-old cancer patient, was also visiting.

Michael Jackson: Every time I talk to him, he is in a better spirit.

Rabbi Shmuley: You're healing him, not just speaking to him?

Michael Jackson: I KNOW I'm healing him. He says, "I need you Michael."  Then he calls me "Dad."  I go, "You better ask your Dad if it is OK for you to call me that."  He goes, "Dad, is it OK if I call Michael 'Dad?'" [laughs] And he says, "Yeah, no problem, whatever you want." [laughs]. Kids always do that and I always feel that I don't want the parents to get jealous that it happens sometimes and it rubs fathers in a strange way. And the kids end up just falling in love with my personality.  Sometimes it gets me into trouble, you know, but I'm just there to help.

Three years later, that boy would accuse Michael Jackson of molesting him during that sleepover visit to Neverland. And though Jackson was ultimately vindicated after a 14-week trial, the charges would forever tarnish Jackson's name.

Meredith Vieira: You went to Neverland. You were there when that boy was there.

Rabbi Shmuley: Correct.

Meredith Vieira: Did you ever see anything untoward?  Did you get the feeling there's something odd here?

Rabbi Shmuley: No, I never saw anything.

And, Shmuley says, the singer had repeatedly -- and emphatically -- denied similar allegations lodged against him in 1993, when another 13-year-old boy who had traveled around the world with Jackson filed a civil suit against him.

Meredith Vieira: All of the attraction that he had to children, and the attention that he paid to children, you believe all of it was innocent?

Rabbi Shmuley: I don't know. What was certainly true is that he wasn't a monster. He may have done something that was unforgiveable even, but that didn't make him a monster.

If the King Of Pop was drawn to children, he was often shy and awkward with women, as you'll hear in candid revelations about his celebrity dates, and crushes, from Madonna to Brooke Shields to Princess Diana.

On Tape, Michael Jackson is a man full of contradictions.

Michael Jackson: I pray when I see something totally magnificent. How could you not see that and go "Wow, what a good God"?

Reflective and grateful at times, so self-absorbed and brazen at others, that he sounds almost delusional about his power.

Rabbi Shmuley: You believe if you were face to face with Hitler you could have...

Michael Jackson: Absolutely.

Rabbi Shmuley: You really think you could have gotten through to Hitler?

Michael Jackson:  Yes.  Mm hmm.

Rabbi Shmuley: By finding the good in him somehow?

Michael Jackson: Yes, I think I could have.  I really do.  I think nobody really talked to him. I hate to say -- brownnosers.  But that's what they were.  That's what he wanted.  That's what they did.

Meredith Vieira: On the one side, he seems to be very self-loathing, hates what he sees in the mirror, insecure. On the other hand, he paints himself to be somebody who could heal sick children, who could turn Hitler around.

Rabbi Shmuley: Unbelievable statements. He was either showing me an incredibly wholesome side that made you fall in love with the kind of person he was, or a strange, bizarre dimension messiah complex. Insatiable for attention.

When it comes to women, the King Of Pop sounds especially conflicted.  He describes his mom Katherine as nothing short of saintly.

Michael Jackson: I don't know anybody like her, she's like a Mother Teresa.  There's very few people like that.

Rabbi Shmuley: He adored his mother and cherished her.

Meredith Vieira: And yet, when he talks about other women, you got the sense that he didn't trust women.

Rabbi Shmuley:  Michael exhibited tendencies of misogyny. That women are materialistic, that women want things from you.

Michael Jackson: Women can do some things that make guys very unhappy. I've seen it with my brothers. I've seen my brothers crying, in tears and pulling the grass out of the lawn out of frustration because of their wives.

Jackson describes women as manipulative, disappointing. Here, he talks about how badly Lisa Marie Presley let him down when she didn't want children.

Michael Jackson: She promised me that before we married, that would be the first thing we'd do is have children.  So I was broken-hearted and I walked around all the time holding these little baby dolls and I'd be crying, that's how badly I wanted it, you know.

For a 42-year-old man, the immaturity that comes across on Michael Jackson's tapes is startling. Sometimes, he sounds just like a teenager.

Michael Jackson: I've never asked a girl out in my life, they have to ask me.

Rabbi Shmuley: Really?

Michael Jackson: Yeah. I can't ask a girl out.

Had he been able to muster up the courage, Jackson told Rabbi Shmuley there was a certain princess who would have been at the top of his list.

Michael Jackson: I liked the way Lady Diana would make her kids wait in line, you know, at amusement parks and things. Like everybody. I thought that was so beautiful. She was good.

Rabbi Shmuley: You felt an immediate connection with her?

Michael Jackson:  Yeah, I loved her very much. Yeah, she was my type, she was my type for sure.

There was no date with Lady Di. But romance was definitely in the air when the King Of Pop stepped out with other high profile celebs. Tatum O'Neal was his first girlfriend.

Michael Jackson: When I held Tatum's hand, I was, like, in heaven. It was the most magical thing. It was better than kissing her, it was better than anything. I remember we went to this club, and I don't go to clubs, which was called the Roxy. And I watching the band, I was sitting there, and underneath the table, she was holding my hand, and I was, like. melting.

Rabbi Shmuley: She held your hand and you felt love?

Michael Jackson: Fireworks going off.

The song “Pretty Young Thing” could easily have been inspired by his affection for Brooke Shields.

Michael Jackson: That was one of the loves of my life. I think she loved me as much as I loved her, you know? We dated a lot.  We, we went out a lot. Her pictures were all over my wall, my mirror, everything.  And I went to the Academy Awards with Diana Ross and this girl walks up to me and says "Hi, I'm Brooke Shields." Then she goes "Are you going to the after-party?" I go, "Yeah." "Good, I'll see you at the party." I'm going "Oh my God, does she know she's all over my room?" So we go the after-party. She comes up to me she goes, "Will you dance with me?" I went, "Yes. I will dance with you." Man, we exchanged numbers and I was up all night, singing, spinning around my room, just so happy.  It was great.

At Jackson's memorial service, Shields would reflect tearfully on their tender bond.

Brooke Shields: When we were together, we were two little kids having fun.

Meredith Vieira: Did you get the feeling talking to him that he ever got beyond that sort of that adolescent approach to romance, the kind of giggly, almost kid-like?

Rabbi Shmuley: For me, it was actually something, you know, it was a blessing to see such a famous man saying that holding hands was suddenly so special. But if you asked me in general, do I think that there was an adolescent quality to Michael? Of course.

It's a quality that made for an odd match with one star who wasn't the least bit shy about doing the asking out:

Madonna (at the MTV music awards): I asked him out to dinner: I said, “My treat, I'll drive, just you and me.”

Jackson was all smiles in the car. But on these tapes, he reveals that the material girl's saucy ways felt more than a little dangerous.

Michael Jackson: You know, at the time I was with Madonna, she was into books, all over, a whole collec--like a library of books of women who were tied to walls, different things.  She said, "I love spanky books." Why would I want to see that? I think she likes shock value.

Madonna laid down the law to me before we went out. "I am not going to Disneyland, okay? That's out."  I said "I didn't ask you to go Disneyland."  She said, “We are going to the restaurant and afterwards we are going to a strip bar." I am not going to a strip bar, where they cross dress. Guys who are, are girls. Said "I am not going to go there,” and I think afterwards she wrote some mean things about me in the press and I said that she's a nasty witch.

Rabbi Shmuley: Michael's tough on Madonna in the book. And he seems to be saying that the reason is that Madonna tried to drag him into a world of prurience. And maybe there was somewhat of a rivalry between them.

Whether it was a true rivalry or not, Jackson does paint Madonna as envious when he talks about jealousy in Hollywood.

Michael Jackson: They admire you and know you're wonderful and great but just they're jealous 'cause they wish they were in your place, wish they were in your shoes.  And "M" is one of 'em.  Madonna. She's not a nice, she hasn't been kind -

Rabbi Shmuley: She's jealous?

Michael Jackson: Absolutely. She's a woman and I think that's what bothers her. Women don't scream for other women. men are too cool to scream for women and i get that. I get the fainting and the adulation and the notoriety but she doesn't. She can't get that.

But like Brooke Shields, Madonna had only fond memories of her time with Jackson when she hailed him in a moving speech at the MTV video music awards.

Madonna: We sat on the couch like two kids, and somewhere in the middle of the film, his hand snuck over and held mine. It felt like he was looking for a friend more than a romance and I was happy to oblige him.

And Shmuley suspects that now, Jackson would be far less harsh on his friend Madge than he was in the tapes recorded 9 years ago.

Rabbi Shmuley: At the time, you know, Madonna had a certain image. She has-- changed that image substantially. Michael -- used to speculate that as a mother, she would change. And he probably would agree with that today.

One thing was clear though -- to the rabbi, Jackson seemed incapable of sustaining any meaningful relationship with a woman. And with no adult love in his life, was the writing on the wall?

He talked about vanishing.

Michael Jackson: I would like to- some kind of way disappear, where people don't see me anymore.

His fear of growing old...

Michael Jackson: I just don't want to look old and start forgetting.

And hauntingly, his own death.

Michael Jackson: When the body breaks down, and you start to wrinkle, I think it's so bad.

Rabbi Shmuley: So you would die before that happens?

Michael Jackson: Uh.. I don't want to grow old.

Rabbi Shmuley:  You don't want to die young?

Michael Jackson:  Um, you're asking me an interesting question.  You sure you want my answer?

He couldn't stand the thought of himself with gray hair --   and at 42, Michael Jackson was already fixated on his final resting place.

Michael Jackson: I want to be buried right where there's children. I would feel safer that way. I want them next to me. I need their spirit.

Meredith Vieira: There are a number of comments that Michael made to you in these tapes that in light of his premature death are-- are eerie.

Rabbi Shmuley: Michael said to me constantly, "If I can't help kids, then I will find a way to terminate my life." 

Meredith Vieira: Did he have a death wish?

Rabbi Shmuley: He lost the will to live.  Did that mean that he consciously wanted to die?  Probably not. I think he was just going through the motions of life toward the end and medicating away almost any kind of human response.

In 2001, after counseling Michael Jackson for two years -- and capturing 30 hours of his innermost thoughts on tape-- Rabbi Shmuley cut ties with the star.

He says the King Of Pop was slipping from his reach, so lured by the pull of fame --  and the seduction of pain numbing drugs  -- that he completely lost interest in their philanthropic projects.

Rabbi Shmuley: For two years, I really felt that I was making headway in helping Michael restructure his life, but once I saw that Michael was treating my advice as if I were a nuisance. I had to end our relationship. Was I gonna applaud as he slowly self-immolated? If I'm just another someone who's afraid to tell him that he's got to stop doing drugs, then what was I doing there?

Meredith Vieira: But was there a part of you, as a rabbi, as somebody who had explored his deepest pain with him, who felt, I'm deserting him?

Rabbi Shmuley: If I had gone back, Meredith, not only would I not have helped him, I would have been dragged into that destructive vortex, and I would have needed help.

To the rabbi, the tragic writing was already on the wall. In 2004, he stated publicly that he feared the worst.

Rabbi Shmuley: That Michael will be dead in a few years. He is headed toward Elvis, Marilyn Monroe, Janice Joplin.  It's almost inescapable. 

Still, the rabbi was devastated, when at age 50, Michael Jackson did suddenly die.

Meredith Vieira: Your initial reaction to his death was anger.

Rabbi Shmuley: My first reaction was, you stupid, stupid man, how could you do this? How could you orphan your children? Your children have no mother. 

Meredith Vieira: Is that what hurt you most, the fact that he is not there to father his children anymore?

Rabbi Shmuley: What hurt me most is that Michael threw away his life, and God endowed this special man with talent that the rest of us could only dream of.  Why did it have to end tragically?

Michael Jackson: I want to always be youthful and have the energy to run around and play hide and seek, which is one of my favorite games.

It is Michael Jackson's own voice, his own words, his deeply personal revelations - that now make the rabbi hopeful that in some way America can make sense of his death, that we can learn something.

Rabbi Shmuley: Michael's life demands redemption.  You can't have someone die at 50 from an overdose and not try to learn some moral lesson.

Michael Jackson: I wanted to become such a wonderful performer that I would get loved back. I was hoping I could get love from other people.

Shmuley believes the book, and the tapes, will help the public see in Jackson a tragic example of what happens when the scars of neglect never heal.

Rabbi Shmuley: A world renowned superstar invites the public into the pain of his childhood, so that parents would learn from that they will now truly understand the horrors that were visited on him.

Meredith Vieira: But forgive me Rabbi, some people are gonna look at the book and say "Well, wait a minute, the book comes out after Michael Jackson has died, but you profit off the book.

Rabbi Shmuley: Well Meredith, let's remember. I've written 21 books, so publishing books is what I do. This book earned a modest advance. Much of the proceeds are gonna be used for organizations that promote family and values. This book is a redemptive book, and it's a beautiful book.

Michael Jackson: I've seen the worst, the nightmare of the human condition, the human soul, of what I would never even think common man would be capable of behaving in such a way.

Meredith Vieira: When you hear his voice now, when you play those tapes over, what do you hear in that voice?

Rabbi Shmuley: It's the saddest thing in the world.  A man trying to break through this-- this cage.  A man trying to break through the people's perception, the fame, saying, "I'm a person."

Rabbi Shmuley:  You're not angry at God, you're not angry at the world?

Michael Jackson:  I'm not angry -- I'm very, taken by it. I'm hurt. I cry an awful lot.

Michael Jackson: I think all my success and fame and - I've wanted it, I've wanted it because I wanted to be loved.  That's all.

Michael Jackson's tapes leave us clues, but like other tragic icons before him, questions will linger for years about the broken soul behind the mask.

© 2013 MSNBC Interactive. Reprints

Video: How ‘America’s rabbi’ met the King of Pop

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