Coolio

Involvement: Actor
Movie(s): Coolio & The Gang Bang (2007)
Famous co-stars: Francesca Felucci
Review: N/A
Complex says: M.C. Hammer and Vanilla Ice may be two of the all-time greatest hip-hop punching bags, but (in some ways) even they didn’t fall off harder than Coolio did. Dude was a legitimate star in the early '90s and he spent 2000s doing guest spots on game shows like Fear Factor and Pyramid before succumbing to making porn (even if it had an inspired title). Couldn't he at least get a stint on Celebrity Rehab?