#1. R Kelly Allegedly Makes A Sex Tape With A 14-year-old Girl
Time Stamp: February 2002
The R. produced, wrote, and sang “Be Careful” with his artist, Sparkle in ‘98. Ten years later, she'd testify during his child pornography trial that the girl having sex with him in a heavily bootlegged video was her 14-year-old niece. Originally sent to the Chicago Sun-Times by an anonymous source, the footage contains what appears to be tossing salad, a golden shower (later to be ingeniously spoofed by Dave Chappelle), and R. giving the girl money. Be careful, indeed.