Diddy

There's no denying Diddy's uncanny knack for success. Formerly known as Puff Daddy, Sean Combs started Bad Boy Records in the mid-1990s, after working at Uptown, producing records for the likes of Mary J Blige and Jodeci. Bad Boy blew up almost immediately, thanks to the hugely popular acts like Biggie and Ma$e among others. After Biggie's murder, Combs became larger than ever before, with multi-platinum solo albums, Grammy awards, etc. He also expanded his empire to incorporate new ventures, including his own clothing company Sean John. Though ridiculously famous and wealthy, he also went through some high-profile trials and tribulations, such as the Club New York shooting (Combs was acquitted; Shyne got 15 years) and getting dumped by hottie du jour Jennifer Lopez. Through it all, he has emerged virtually unscathed, and continues to play both sides of the fence, working with pseudo-thug rappers and hobnobbing in the Hamptons with the ultra-rich. In 2002, his compilation LP We Invented The Remix debuted on the charts at number one. He subsequently released The Saga Continues... in 2005 and continues to be a pop icon that is revered by his fans. He subsequently released The Saga Continues... in 2005, and dropped Press Play the following year. On Press Play, Diddy continues to raise the bar for platinum braggadocio rap. A great pop record, it reasserted Diddy's continued relevance in the hip-hop world.