Net Worth: $30 million
Hustles: Grand Hustle Records, Club Crucial nightclub ownership, VH1 reality show, various acting jobs, endorsements with Chevrolet,, AXE body spray, and Rémy Martin Cognac.

The self-proclaimed "King of the South" once was the King of Endorsements too. From 2007 to 2010, he racked up multiple deals, and was even named the Global Creative Consultant of Rémy Martin Cognac, with an eye towards developing his own liquor line. Due to his multiple arrests and jail time, however, he's now lost all of his endorsement deals. He has a new album due later this year, so with a strong release and a clean record, Tip could get back to that corporate dollar. In the meantime, he's certainly earning from his successful VH1 reality show.