Call it Diddy's first empire. The Harlem native, after a stint as an intern at Uptown Records in the early 1990s, launched his infamous Bad Boy Records label in 1993 with flagship artists Craig Mack and The Notorious B.I.G., going on to sell millions of albums and change the face of hip-hop and music in general along the way. Many of the artists who came through Puff's storied imprint are household names: Biggie, of course, but also Faith Evans, New Edition, Ma$e, Total and plenty more.

But while Bad Boy has enjoyed an extended run as one of the most influential hip-hop labels in history, it's also had its share of ups and downs. Biggie's death in 1997 stopped one of rap's greatest icons in his tracks at the age of 24; Shyne was locked up for eight years after the notorious Club New York shooting involving Puff and J. Lo in 1999; Ma$e retired the same year while he was arguably at the top of his game in order to dedicate himself to his faith; several other high-profile signees either never got off the ground or disappointed with their production, leading them to exit the company. These days, Bad Boy's roster boasts just four artists: French Montana, Machine Gun Kelly, Diddy himself and his girlfriend Cassie.

Earlier this month, the hip-hop mogul announced that he'd signed a label partnership deal with Epic Records, bringing Bad Boy out from under the Interscope umbrella and over into the Sony camp as he prepares to release two new albums, a solo LP and No Way Out 2, a followup to Puff Daddy and the Family's beloved 1997 project. As Diddy prepares for another new chapter in Bad Boy's long history, XXL takes a look back at 34 artists who have left the label over the years.