Season 5, Episode 6
Ari heads to the green to take on Alan Gray (guest star Paul Ben Victor) in a game of golf, hoping to win Vince the role in Smokejumpers. But Ari realizes that he's got his work cut out for him when he meets Gray's new coach -- professional golfer Phil Mickelson (as himself) -- and Gray invites Bob Ryan (guest star Martin Landau) to join them, just to annoy Ari.
Meanwhile, Vince convinces Drama to hire Turtle as his new assistant, and he grudgingly agrees - putting Turtle through the paces. Just as Eric is about to take his client Charlie (guest star Shad Moss aka Bow Wow) to a pilot pitch, Vince gets a call from their old friend Dom (guest star Dominic Lombardozzi), who needs bailing out of jail. Eric doesn't buy Dom's story, but Vince convinces Eric to put up the money. Nevertheless, a nervous E insists on keeping Dom in his sights all day, not wanting to lose his $100K. When they finally head back to Dom's house and discover that his story holds up, E feels bad -- especially when Dom's new wife takes off with their baby when she learns Dom was arrested. Turtle quits after a day under Drama's thumb.
Back on the golf course, it turns out Alan Gray has been hustling Ari. When Gray turns on the heat, Ari loses big - until Alan vents his rage, collapsing dead on the course.