Crime: Third-Degree Assault
Verdict: Pleaded Guilty
Sentence: Three years of probation.

In 1999, 29-year-old Jay-Z was fresh off the release of “Hard Knock Life (Ghetto Anthem),” a smash single that broke the rapper to an entirely new audience the previous year. Multiple hits from Hard Knock Life… Vol. 2 had charted, the album ultimately went five times platinum, won a Grammy, and Jay even snatched a guest spot alongside Mariah Carey on her massive single “Heartbreaker.”

His follow-up, Vol. 3… Life and Times of S. Carter, debuted at No. 1 on Billboard, but the album was heavily bootlegged prior to its release. On Wednesday, December 2, 1999, Jay-Z had a listening party for the album at Irving Plaza in NYC. He hit the stage alongside Beanie Sigel, Amil, and Memphis Bleek while Dame Dash yelled “Fuck the bootleggers!” into the microphone.

Later that night, at the now-defunct Kit Kat Club in midtown, Jay attended Q-Tip’s album release party. While Q-Tip was being interviewed in another part of the club, Lance “Un” Rivera, a record promoter, was stabbed in the abdomen and shoulder. After being sought by police, Jay turned himself in the following day.

At first, the rapper denied any involvement, but ultimately pleaded guilty for the stabbing, a third-degree assault charge, rather than face a potential 15-year jail sentence should he lose the case in court.