Michael Jackson was born on 29 August 1958.
This is a typical rags to riches story as you can see the hard life followed by the easy life in the timeline. His first stroke of luck comes in his Libra phase, in 1969, where he has Jupiter (planet of luck and prosperity) in Libra.
This is followed later by his stupendously popular Thriller album in 1982, in his Sagittarius phase, towards, the end. He has Saturn (authority, hard work) conjunct midheaven (career, image) in late Sagittarius in his natal chart, supported by Mercury (communication), Venus (likability) and Uranus (unpredictability) in Leo.
At the bottom of his timeline and in the first year of Capricorn phase, in 1984, he sustains a face injury which would go on to be the subject of much controversy and ridicule as well as a whole new look. This would be the base rock upon which he would build his career.
In 1993 he is in the public spotlight for child molestation charges, in his Aries phase. Opposite sign, Libra is about justice, where he has Jupiter, the planet which gave him his initial, lucky break, and he is hauled to court for more reasons than one could count.
1n 1994 he has a very public and legacy-cementing marriage with Lisa Maries Presley, the daughter of Elvis Presley, King of Pop. This is also in his Aries phase where he is supported by Saturn (legacy, solidity) conjunct Midheaven (career, image) in Sagittarius.
He dies in 2009 from a drug overdose in his Cancer phase. Cancer is the sign of drugs, overdoses, mental illnesses, etc. It is also a sign associated with deep losses, pain and suffering.