Diddy is just 3 years old when his father, Melvin, a street hustler, is shot to death in Manhattan's Central Park. Soon after, his mother Janice moves the family from Harlem to a suburb just north of the Bronx. As an adolescent, he soaks up the rising hip-hop scene in '80s Harlem. In the fall of 1988, he attends Howard University, studying business administration, but his real education comes when he leaves in 1990 for an internship at New York record label Uptown Records.
After a two-year rise from intern to vice president at Uptown Records, Diddy promotes a charity celebrity basketball game at City College of New York and more people arrive than can fit in the hall. When organizers start to close the doors, a stampede ensues; nine people are killed and 29 seriously injured. Diddy isn't criminally charged, but pays out an undisclosed amount in civil lawsuits.
Two weeks after being fired from Uptown Records, Diddy forms Bad Boy Records. He produces Ready to Die, the legendary debut album by 22-year-old Brooklyn rapper, The Notorious B.I.G. The record's success establishes both as emerging stars and cements their bond. Diddy makes a name for himself as a producer with more albums by Mary J. Blige, Faith Evans, 112 and Mase.
After leaving a Vibe magazine party in L.A., The Notorious B.I.G. is shot to death by an unknown assailant. Diddy is riding in the vehicle ahead of B.I.G.'s. Police speculate that the shooting might be retaliation for the September 1996 murder of rapper Tupac Shakur, who had been feuding with Diddy and B.I.G. "There's definitely no truth in that," Diddy tells Time. "He did not deserve to die. Our problems were some record-type s---."
Diddy releases No Way Out, his first solo album as a performer. The chart-topping record produces a number of hit singles like "It's All About the Benjamins" that raise Diddy's already larger-than-life reputation. "I like talking about money, fantasy and cars, but it's not like that's all I think about," he tells Ebony. "We all fantasize about money. The problem is when people scrutinize it too hard and try to make something that is supposed to be fun into a politically conscious statement."
Although the two are no longer together, Diddy's ex-girlfriend, Kim Porter, gives birth to his second child, Christian. (Diddy has a son Justin, 4, with fashion stylist Misa Hylton-Brim.) Fatherhood is "one of the greatest joys of my life," he tells Ebony. "[It] has taught me about life and about how to love more."
Calling it "the future of fashion," Diddy introduces his Sean John clothing line for men and boys. "I always had the idea that I would start my own apparel line," he tells DNR, the men's fashion magazine. "I wanted to make sure the timing was right." In 2004, he expands with a women's line and scent, and is named the year's best menswear designer by the Council of Fashion Designers of America.
Diddy spends $600,000 on his 29th birthday party at Manhattan's Cipriani restaurant, hosting Muhammad Ali, Mariah Carey, Martha Stewart and the Duchess of York, among others. The exclusive guest list and fancy surroundings are becoming trademarks of Diddy's lavish shindigs, whether in the city or at his Hamptons mansion. "Where else but at a Puffy party would Busta Rhymes get to meet the Duchess of York?" asks party planner David Watkins in PEOPLE.
After months of speculation, Diddy and star Jennifer Lopez admit they are a couple. Friends for years, the pair began seeing each other romantically in 1998 and make a splash in matching white outfits at Diddy's elaborate Labor Day party. "I've never had anyone love me the way [Jennifer] loves me," Diddy says at his birthday bash in November (at which Lopez dresses as Marilyn Monroe). "Hopefully one day I'll be able to marry her."
Diddy and Lopez are arrested after a shooting at Manhattan's Club New York results in three wounded. Driving away with their chauffeur and bodyguard in a Lincoln Navigator, the couple runs 11 red lights before police pull them over, finding a loaded 9mm by the passenger seat. Lopez is free after 14 hours at the station, while Diddy faces 15 years in prison on gun charges. He is acquitted in March 2001.
BIOGRAPHY (top to bottom): Classmates Yearbook Archives; Venus Bernardo-Prudhomme/Pacha/Corbis; TSUNI/GAMMA; Michael Loccisano/FilmMagic; Marion Curtis/DMI/TLP/Getty; Michael Diamcfadden/Big Pictures