Season: 5
Air Date: September 21, 2008

The main mission of any long-running TV show should be to avoid repetition—we're looking at you, Dexter. Entourage's fifth season is all about shaking up the status quo and making the boys poor, and no episode is more dedicated to that storyline than "The All Out Fall Out," which finds the once mighty Vincent Chase relegated to appearing at a spoiled brat's sweet 16 to get out of the red, exposing cracks in his self-acclaimed dignity.

The episode still manages to stroke the quintessential guy fantasy with Ari in full alpha-male mode, complete with a brand new Ferrari, bitching out a nemesis agent in front of all his peers and coming home to a hot wife, all on his birthday.