1. "Vegas Baby, Vegas!"
Air Date: August 6, 2006
The final minutes of this episode are the funniest Entourage has ever delivered. It goes a little something like this: Vince and the gang co-opt Ari into a last minute trip to Vegas to blow off some steam. And from there everybody takes a backsteat to E and Drama as we're given dual storylines from both that unexpectedly converge with hilarious results.
Playing a fantastically douche-bag version of himself, Seth Green repeatedly pops up around town to taunt E about his and Sloan's history together, meanwhile the friendship between Drama and his male masseuse gets more and more suspect as the episode progresses. By episode's end, you'll never be able to hear the name Jackson Pollack again without smirking.