Year: 2009 (Season 6, Episode 12)
Cameo role: Himself
In this cameo, LeBron James plays himself and appears alongside Matt Damon, who has been ragging on Vince for not doing enough for charity for weeks. James and Damon engage Vince, Turtle E, and Drama in some light charity competition (“I gave a million, Vince,” is just such a great line). It’s some pretty classic Entourage—there’s Vince literally yelling about a $150,000 check across a private airfield—made all the better by reminding you that LeBron James will always be ten times cooler than any of the guys on Entourage. Combined.