20 Years Later: ‘Entourage’ Had Over 100-Guest Stars, Who Were the Top 10?
Few TV shows provide a peek into the Hollywood lifestyle as well as Entourage, which debuted 20 years ago. While every episode of the show focused on up-and-coming actor Vincent Chase (Adrian Grenier), his brother and fellow actor Johnny Drama (Kevin Dillon), his agent Ari Gold (Jeremy Piven), and his friends Eric (Kevin Connolly), and Turtle (Jerry Ferrara), Entourage is also loaded with famous celebrity guest stars over its eight-season run (2004-11).
Some familiar names are onscreen as nothing more than quick name drops (mostly athletes) while others have multiple episode story arcs (Mandy Moore, James Cameron, Bob Saget, etc.). However, the most memorable actors that are hard to forget only appeared once. Entourage had more than 100 guest stars but these are our picks for the 10 that were so good they were one and done.
Christian Slater (Season 8, Episode 2)
In a blink-and-you’ll-miss-it-scene, Christian Slater throws double birds at Drama while walking across a studio lot and he has no idea why. The moment is never addressed again but it’s random, silly, and continues the series-long narrative that Drama is terrible to work with.
Sofia Vergara (Season 4, Episode 1)
While filming Medellin in Colombia, hot-headed director Billy Walsh (Rhys Coiro) hires a local actress to appear in the film. Listed on IMDB only as “Village Girl” and filmed two years before her breakout in Modern Family, Sofia Vergara’s beauty proves to be a major distraction for Walsh, who wreaks havoc with the cast and crew.
Val Kilmer (Season 1, Episode 5)
Eric Roberts (Season 5, Episode 5)
Speaking of sherpas, if you’re looking for mushrooms in Hollywood the man to see is evidently Eric Roberts. The winnebago driving actor takes the gang to Joshua Tree to help Vince make a major career decision. As you might expect, the episode is a trip.
Brooke Shields (Season 2, Episode 11)
Mistakenly believing he was cast as Brooke Shields‘ love interest in a movie of the week, Drama disappointingly learns he’s playing her brother. A life long crush leads to an amazingly awkward situation during filming, which gets Drama fired.
Jessica Alba (Season 1, Episode 2)
An old friend of the boys, Alba invites Vince and his crew to a party to pick their spirits up after a bad film review. The Fantastic Four actress is mentioned several times during the show’s run and Vince and company even stay at her Malibu beach house in Season 2.
David Schwimmer (Season 6, Episode 4)
Typically on Entourage guest stars play themselves straight but every now and then an actor plays against type. Known as geeky, neurotic Ross Geller on Friends, in his cameo David Schwimmer plays a lecherous version of himself, trying to score with one of Ari’s agents.
Vanessa Angel (Season 2, Episode 9)
Johnny Drama has issues with almost everyone from his past, including former Viking Quest costar Vanessa Angel. He was rude to her back in the day because he was attracted to her and didn’t know how to handle it. This is the rare episode where viewers see Drama succeed romantically.
Ralph Macchio (Season 2, Episode 3)
Banned from the Playboy Mansion and unable to attend its famous pajama party, Drama goes to the home of The Karate Kid, Ralph Macchio. Mistakenly believing Macchio is the one who got him banned, they eventually work together to learn the culprit is Pauly Shore.
Matt Damon (Season 6, Episode 12)
In perhaps the show’s funniest cameo, Matt Damon follows up with Vince to see if he’s read the information sent to him about the OneXOne Foundation. This was an actual non-profit Damon was an ambassador for at the time. Over the course of the episode, Damon “Jason Bourne’s” Vince into making a big donation, with a little help from Bono and LeBron James. Damon’s post credit scene is the hilarious icing on the cake.
Classic Hollywood Hunks
September 2019
Cary Grant, Sean Connery, Rock Hudson and Paul Newman, smoldered onscreen and, in addition to being smokin’ hot, they were effortlessly cool.
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