Entourage's 15 Craziest Celebrity Cameos

When Ari makes the mistake of bringing Vin Diesel to a Laker's game he promised to take Larry to, Larry takes the snub very personally. Ari attempts to sweet talk his way out of the debacle, but, of course, Larry isn't having it and launches into an epic rant. Drama swoops in with a tension-cutting save and, in typical Drama fashion, propositions Larry for a spot on Curb Your Enthusiasm. Bottom line? Nobody puts Larry in a corner. 

T.I. is insulted by the stereotypical scripts being pitched to him ("Look at this shit: gangster, drug dealer, rapper. I might as well be playing myself!") and looks to Ari to land him a more serious role.  Specifically, he wants to play a supermarket employee who falls for an older woman and is jonesin' for that older woman to be Meryl Streep.

His requests are cut short when Ari is questioned by cops for sending feces by way of U.S. Mail (for one of his revenge plots, of course), and even T.I. is freaked out ("You are literally on some sick shit, Ari."). But it turns out Ari isn't under arrest, he's just in for a filthy surprise of his own.

Like any good Giants fan, Turtle talks big game about his plans to hate on Tom Brady, but he loses his resolve at a truly pathetic rate. He starts strong, conveniently "forgetting" to bring Brady a drink, but quickly backs down when Brady mentions his ultra-sexy wifey Giselle is a fan of his girl, Jamie-Lynn Sigler. In a matter of minutes, Turtle becomes putty in Brady's hands and Mark Wahlberg is the first to call him out for it: "Why don't you stop staring at the guy like you want to fuck him." We're with Marky Mark on this one. Show some team pride and at least eye-fuck Eli Manning.

We like two-for-ones, and cameos are no exception. In this clip, E is torn between two sexy women: Monica Keena (playing his girlfriend) and Holly Valance (playing his temptress). Holly convinces E to hook up with her the night before with some solid reasoning ("But you're not in love.") and isn't thwarted by his taken-status in the a.m. either. In fact, she's downright incredulous that E might leave before going for round two ("Oh please, I've never been with a guy who didn't want to fuck me again in the morning.") and honestly, we don't blame her. Guilt or no guilt, passing up on seconds of Valance in the morning is practically a sin in itself.

There are a few choice adjectives one might associate with Mike Tyson, but wholesome certainly isn't one of them. So, when Tyson tells Ari that he wants to do "a real TV show," specifically a black Brady Bunch, even Ari struggles to maintain a straight face. When their chat is interrupted by a call from Jessica Simpson, Tyson exclaims she'd be "a hot Carol Brady" and begs Ari to get her involved. 

The guys run into Kanye West in the airport, and convince him to fly them to Cannes. Once on board, Kanye announces he will personally be flying the plane and that the flight attendants will be offering massages. Luckily, Yeezy is kidding about flying the plane, but the girls offering massages ("I'm hot stone, she's shiatsu.'") are the real deal.

While trying to court John Stamos to co-star in a new show, Drama makes the mistake of beating him in a ping pong match. Stamos is confident the win was merely a fluke and challenges Drama to a re-match, taunts him ("Johnny, you're a bitch, you know that? A real pussy."), and clowns his "cum-stained" table. Drama, desperate for a gig, agrees to play Stamos again for the opportunity to do a TV show with him. Because who wouldn't want to spend more time with a douche like that.

When Liddell goes after the same parking spot as him, Drama, armed with no knowledge of Liddell's skull-crushing capabilities, and suspecting that he's being punked, refuses to back down. He challenges the fighter, saying, "Why don't you and your hoopty move along," and calls him a "WWF wannabe." Lidell is infuriated by Drama's smack talking, or maybe just entertained by his stupidity, and keeps his cool: "You're lucky my daughters in the car. I'd kick every tooth in your head out."

Vince stumbles upon a robed Bob Saget, complete with cigar in his mouth, sandwiched between two bikini-clad women. Saget pulls Vince aside to congratulate him on landing Staci and admits he once offered her a hundred grand and she still wouldn't sleep with him. He inadvertently informs Vince that Staci is a lady pimp, saying, "It's not everyday somebody scores the Madam." Sagat solidifies his solid cameo by taking bong hits with Drama and Turtle and cockblocking Drama by luring his potential lady away with promises of Courvoisier.

Honorable mention: Saget welcomes Vince to the neighborhood with a fruit basket and a warning: "Do me a favor, don't fuck 'em. Don't you fuck my daughters."

Fresh off a break-up with porn star Sasha Gray, and under the influence of a potent cocaine and painkiller cocktail, Vince runs around Eminem's party propositioning every attractive female he sees for sex. But, when he extends a gracious offer to Minka Kelly ("Do you want to fuck tonight?"), he apparently crosses the line. Eminem and his bouncer swoop in and Vince eggs him on ("Too mainstream now to fight your own fights, Marshall?") until Eminem duffs him and knocks Vince the fuck out. 

Gary Busey does an amazing impression of himself (or maybe it's not even acting?), creeps Turtle out ("You scare me Gary!"), and offers Drama a shot at immortality by way of "enlightened photography," which turns out to be Busey throwing paint at a shirtless Drama while chanting in an unknown language. The look on Drama's face when the first splatter of paint hits him in the face qualifies Busey as one of Entourage's most bizarre cameos ever.

Matt Damon drives a hard bargain. With the help of LeBron James and Bono, Damon straight up peer pressures Vince into donating to a children's charity he heads. He spends the entire episode running a serious guilt trip on Vince and finally "Jason Bourne's" him into coughing up the cash. When Vince's check doesn't arrive in the mail, Damon has an epic breakdown, hysterically screaming, "Give me the fucking check, Vince! I can't believe I have an Academy Award and I'm calling YOU back. Again and again and again! You cocksucker! Send me the check!" and proceeds to burst into tears.