The Moment: In June 2007, Lupe Fiasco's business partner Charles "Chilly" Patton was sentenced to 44 years in prison on drug charges.
The Reaction: Though Chilly denied—and continues to deny—any wrongdoing, most people were pretty surprised to hear that Lupe was connected to someone going away for that long on drug charges.
Did It Help or Hurt His Career? HURT! But, in the long run, Chilly's imprisonment didn't impact what people thought about Lupe.