Entourage's 15 Craziest Celebrity Cameos

From the sexy to the strange, we showcase Entourage's wildest celebrity cameos.

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Image via Complex Original
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After seven seasons filled with models, exotic locales, and schmoozing, the holy grail of testosterone television, HBO's Entourage, is finally coming to a close with its eighth and final season, which premieres this Sunday night. We're going to miss the booze, babes, and mayhem, but also the regularity with which Vince and the boys hob-knobbed with our favorite celebrities. With cameos as endless (usually one or two major celebrities, often half naked or half baked, per episode) as Vince's many sexual conquests, you may have forgotten some of the gems that HBO has provided, but we haven't. So, sit back, relax, and gaze at the stars as we count down Entourage's 15 Craziest Celebrity Cameos.

15. Larry David Reems Ari Out

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14. T.I. Wants To Make A Movie With Meryl Streep

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13. Mark Wahlberg Exposes Turtle's Man Crush

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12. Holly Valance Encourages Repeat Cheating

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Pauly Shore Uncages Hugh Hefner's Monkey

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Drama is questioned about the dissapearance of a monkey during a party at the Playboy Mansion by Hugh Hefner, who has Kendra Wilkenson and Holly Madison on either arm. When Hugh threatens to toss Ralph Macchio (yes, even the Karate Kid himself joins the party) and Drama out if they don't immediately reveal the culprit, the boys suddenly remember that Pauly Shore is the zoo-napper. We then see Shore forcibly removed, kicking and screaming all the while.

10. Mike Tyson Wants To Star In A Black Brady Bunch

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9. Kanye Pilots A Plane For the Boys (Or Not)

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8. John Stamos Is A Sore Ping Pong Loser

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7. Chuck Liddell Spares Drama's Life

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6. 50 Cent Clowns Turtle's Ride

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Scenario: 50 recognizes Turtle at a traffic light, but Turtle's excitement (50 knows my name!) gives way to embarrassment when the rap star hates on his powder blue Ferrari, which was a gift from Vince. 50 prods Turtle ("What's up, man? See you out here in daddy's car. Don't be somber, at least you look good.") and lets out what could only be described as a condescending giggle as he pulls off in his Bentley.
 

5. Raunchy Bob Saget Cockblocks Drama

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4. Eminem Punches Vince In The Face

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3. Gary Busey Offers To Paint Drama Naked

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2. Val Kilmer Gets High And Almost Shoots E

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Kilmer plays "The Sherpa," a hemp-obsessed pot dealer who spouts off philosophical absurdities while getting the guys high ("Everything is evolving. Turtle, you are a dove."). When E's cell phone interrupts his anti-authority speech, he whips out a pistol and points it at E, screaming "Don't touch it!" Paranoid hippies make for great cameos.
 

1. Matt Damon Pressures Vince Into Charity

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