Season: 3
Air Date: May 13, 2007

You rarely find yourself feeling sorry for these guys, for the simple reason that the Entourage crew members almost always get everything they want. That is, except for Drama, whose pathetic career spiral is often played for laughs.

So as Drama seems to be getting teed up for yet another public failure with his new TV show, nothing was more surprising than the decidedly unfunny shot of him driving off into the night crying. After three and a half seasons of bad luck, nothing was more rewarding than Drama waking up in his Lincoln to the boys plus Lloyd calling to tell him his premiere was a hit. Victory!