In an exclusive video obtained by 48 Hours, Jackson even seemed to have dressed the 13-year-old up to look like himself. But just a few weeks after the video was taken, the boy accused Jackson of a sex crime.
Jackson's current legal troubles bear a striking resemblance to the first time he faced and escaped charges of pedophilia.
In light of this week's allegations, brought on behalf of another young boy, many are recalling that first case. MTV News Correspondent Kurt Loder looks at the 1993 child molestation case against Jackson.
Michael Jackson has always surrounded himself with young boys – but his relationships with them weren't seriously scrutinized until 1993.
Jackson had started that year acknowledging, and trying to change, his public image as a strange and isolated figure. He sat down with Oprah Winfrey, and he hobnobbed with the president.
That Jackson was "different" had long been clear. Still, even veteran Jackson-watchers were startled when California authorities announced in August 1993 that they were investigating the singer for an alleged child sex crime.
In September, the 13-year-old filed a civil suit against Jackson, charging sexual battery. Jackson, who was out of the country at the time on a world concert tour, avoided acknowledging the charges against him back home.
His 1993 world tour grew increasingly strange. In South America, he was photographed with two young boys who were traveling with him. He was holding up a copy of a magazine called "Child."
And, with a concert date looming in Puerto Rico – a U.S. jurisdiction -- Jackson suddenly cancelled the rest of his world tour, and claimed he had become addicted to pain killers prescribed after scalp surgery, for an accident that had occurred a decade earlier.
With his tour cancelled, and his multi-million dollar promotional deal with Pepsi-Cola suddenly terminated, Jackson flew from Mexico to Europe -- pointedly avoiding any touchdown on U.S. soil. Back in LA, his lawyers denied he was avoiding returning to the U.S. for fear of legal consequences.
"He's a pedophile. He's king of the pedophiles," says Ernie Rizzo, a private investigator hired by the boy's father to investigate what happened with Jackson.
"When they took the statement from the kid, he described in great detail, all of Jackson's genitals, what scars, what marks, what little brown circles were all over it," says Rizzo. "And then when the judge issued a warrant for Jackson to be photographed in the nude, it was perfect to what the kid described. That was the cincher for me."
In December of 1993, Jackson returned home. Authorities were waiting for him, and ordered a strip search that resulted in having his genitals photographed.
"It was the most humiliating experience of my life one that no person should ever have to suffer," said Jackson, at the time of the incident. "It was a nightmare. A horrifying nightmare, but if this is what I have to endure to prove my innocence, my complete innocence, so be it."
Jackson never stopped proclaiming his innocence, but according to journalist Maureen Orth, he also tried to intimidate the boy's family.
"What happened was that his father got a dead rat in the mail, his office ransacked, he was beat up," says Orth. "The boy and his nanny were out walking one day, and a speeding car, the boy was on his bike I believe, and a speeding car came right at them and knocked him, brushed him off his bike. They were very much intimidated and scared."
Jackson also sought to pay the family off.
"Well, when [Gil] Garcetti, the district attorney, kept stalling, and dragging their feet, and Jackson kept waving money in one hand, the father had to make a decision," says Rizzo. "Do you take the $20 million or do you keep waiting until something happened to Jackson and maybe nothing would ever happen?"
In January 1994, Jackson reached an out-of-court settlement in which it was agreed the child would drop his civil suit in exchange for a reported $20 million. The settlement also derailed any possible criminal case.
Four months after the settlement, in a startling move, Jackson married Lisa Marie Presley. The marriage lasted 20 months. But less than a year after divorcing Presley, Jackson married his dermatologist's assistant, Debbie Rowe, who subsequently gave birth to two children: Prince Michael and Paris.
In 1997, there suddenly appeared a book called "Michael Jackson Was My Lover" -- a so-called secret diary. It included the boy's sketches of Jackson's apparently distinctive genitalia. The singer took no action to have the book withdrawn.
Now, a decade after Jackson's last under-age sex scandal, here he is once again, charged with molesting another young boy. He has a new single out -- written by another child-sex suspect, R-Kelly. Its title: "One More Chance."
"He wants you to think that he's this little Peter Pan," says Orth. "And that also helps seduce children if they think you're this harmless little child yourself, instead of a canny, shrewd, show business figure who has a long history of this sort of behavior with little boys."
"I'm not surprised at this arrest at all. I think he made a big mistake by coming on television six months ago and saying he loves little boys and there should be nothing wrong when I sleep with them," says Rizzo. "Jeez, can you imagine the guy next door saying that? I don't know what's wrong with people. It's so obvious it's sad."