Jackson was born in the borough of Queens, New York City, and raised in its South Jamaica neighborhood by his mother, Sabrina. A drug dealer, Sabrina raised Jackson until she died in a mysterious fire when Jackson was 8. After his mother's death and his father's departure Jackson was raised by his grandmother. He began boxing at about age 11, and when he was 14 a neighbor opened a boxing gym for local youth. "

On May 24, 2000, Jackson was attacked by a gunman outside his grandmother's former home in South Jamaica. After getting into a friend's car, he was asked to return to the house to get some jewelry; his son was in the house, and his grandmother was in the front yard. After Jackson returned to the back seat of the car, another car pulled up nearby; an assailant walked up and fired nine shots at close range with a 9mm handgun. Jackson was shot in the hand, arm, hip, both legs, chest and left cheek. His facial wound resulted in a swollen tongue, the loss of a wisdom tooth and a slightly slurred voice; his friend was wounded in the hand. They were driven to a hospital, where Jackson spent thirteen days. The alleged attacker, Darryl Baum, Mike Tyson's close friend and bodyguard, was killed three weeks later. Jackson recalled the shooting: "It happens so fast that you don't even get a chance to shoot back .... I was scared the whole time ... I was looking in the rear-view mirror like, 'Oh shit, somebody shot me in the face! It burns, burns, burns.'" In his autobiography, From Pieces to Weight: Once upon a Time in Southside Queens, he wrote: "After I got shot nine times at close range and didn't die, I started to think that I must have a purpose in life ... How much more damage could that shell have done? Give me an inch in this direction or that one, and I'm gone". After using a walker for six weeks, Jackson was fully recovered after five months. When he left the hospital he stayed in the Poconos with his girlfriend and son, and his workout regime helped him develop a muscular physique. In the hospital Jackson signed a publishing deal with Columbia Records before he was dropped from the label and blacklisted by the recording industry because of his song, "Ghetto Qu'ran". Unable to work in a U.S. studio, he went to Canada. With business partner Sha Money XL, Jackson recorded over thirty songs for mixtapes to build a reputation. In a HitQuarters interview, Marc Labelle of Shady Records A&R said that Jackson used the mixtape circuit to his advantage: "He took all the hottest beats from every artist and flipped them with better hooks. They then got into all the markets on the mixtapes and all the mixtape DJs were messing with them." Jackson's popularity increased, and in 2002 he released the mixtape Guess Who's Back?. He then released 50 Cent Is the Future backed by G-Unit, a mixtape revisiting material by Jay-Z and Raphael Saadiq.

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