If he could go back and give himself some advice at age 9 or 10, the approximate age of his oldest children, he would advise himself, "if you are going to do it, commit yourself, know your craft and be really involved." He'd say to be strong and to have "rhinoceros skin" when it comes to dealing with the pressures of fame.
Perhaps Jackson learned to have a thick skin after enduring years of controversies.
Born Aug. 29, 1958, in gritty Gary, Ind., Jackson rose to fame as the youngest member of the brother act, The Jackson 5. The group released its first single on the Motown label in 1969, when Jackson was 11 years old, and enjoyed a string of hits in the early 1970s.
The group eventually became known as The Jacksons, and Jackson also had hits as a child solo artist and actor.
Jackson's adult musical career took off with "Off the Wall," and eventually, he became such a superstar that he adopted the moniker, "the king of pop."
But Jackson also developed a reputation for eccentricity. He often was seen wearing a surgical mask in public, and his appearance changed and his skin complexion seemed to grow lighter through the years.
He had a pair of brief marriages, including one to Elvis Presley's daughter, Lisa Marie Presley.
In 2002, Jackson drew criticism for dangling his youngest son, Prince Michael II, then a toddler, from a German hotel balcony as fans looked on. He later apologized.
In 1993, Jackson was accused of molesting a 13-year-old boy who visited his "Neverland" ranch, but settled the case out of court.
Jackson was criminally charged with child molestation in 2003, but was acquitted in 2005.
Is the Thriller Gone?
"Fifty should have been a turning point for him," said the man known only as Phoenix, who once served as a spokesman for the Jackson family and now fronts a tribute band called the Dancing Machine Revue. "The Big 5-0, so far, is not going quite as planned."
After the trial, the family relocated to Bahrain as Jackson fled the media he once courted. Jackson recently returned to the States and has been living in Vegas where he was photographed last month being pushed in a wheelchair while wearing a dreadlocked wig, sunglasses and a surgical mask.
The photo seems to contradict Jackson's own comments that he feels young and can still perform his famous dance moves.
When Jackson biographer Stacy Brown saw it, he thought, "Oh, he's looking for attention again," he said. "Then, I looked closely and said, 'Wow, he's really thin. Maybe there's a problem."
Brown, who was once close to the family and collaborated with Jackson's brother Jermaine and sister Rebbie on books, said Jackson's has a history of physical ailments. "He's battled lupus for years, especially when he's in a high-stress situation. And he's been under that for long time."
He has also battled addictions to pain medications and can put away a surprising amount of whiskey, said Brown, co-author of "Michael Jackson: the Man behind the Mask."
But Phoenix believes it's his emotional demons that are crippling him now.
"He's been under the weather for a while, but I believe it's more or less psychological," he said. "The world has always expected him to be energetic and lively. He has a lot to live up to."