the years: 2004-2011
the seasons: 8
the episodes: 96
the creator: Doug Ellin
the top directors: Julian Farino (23 episodes) & Mark Mylod (23 episodes)
the top writers: Ally Musika (21 episodes) & Rob Weiss (20 episodes)
- Kevin Connolly as Eric Murphy
- Adrian Grenier as Vincent Chase
- Kevin Dillon as Johnny ‘Drama’ Chase
- Jerry Ferrera as Turtle
- Jeremy Piven as Ari Gold
Just a few things before you scroll down. While thinking about this list I pretty much made a “3 episodes or less” rule. It’s straightforward, but means to make this list the actor/actress playing him/herself cannot have been on the show more than 3 times. It was a tough call, but it also helped make the list short.
Sadly this means no Bob Saget or Sasha Grey, no Mark Wahlberg or Andrew Dice Clay, and definitely no Jamie-Lynn Sigler or Mandy Moore. My advice, watch the show. You will see them all there, sure there might be some f-words and nudity along the way, but I have faith you will manage.
the episode: “The Review“ (S.1, Ep.2)
If you know anything about me you would know it was an absolute necessity to put J-Alb’s on this list. Although the show doesn’t give her anything spectacular or memorable to do, I still believe her presence added to the show. Entourage was in its infancy, needing a-listers to back up its legitimacy and create a fictional “real life of the stars” aspect the audience would eat up. High school crush aside, Jessica Alba was one of the first pioneers and an essential building block in creating the “who’s who” for the show.
the episode: “Busey and the Beach” (S.1, Ep.6)
Gary Busey had a few cameos on the show, but his first was the most memorable. He already has the “crazy” reputation, and Entourage decided to play with that, a lot. Busey tries to break into the world of modern art and inevitably, comedy ensues. We assume Busey’s weird, so when he portrays himself in such a weird way it feels normal. Gary Busey’s character is near impossible to forget no matter how hard you try, and so will his cameo.
the episode: “Aquamansion“ (S.2, Ep.3)
First of all, this episode was amazing. Maybe it’s the dude in me, but any episode involving the Playboy Mansion is bound to be memorable. The show takes advantage of Macchio’s never-fading glory from The Karate Kid to have a little fun. Johnny Drama wants in to the Mansion, but had a lifetime ban slapped on him back in the day after being falsely accused of something he didn’t do. His only chance for redemption is getting Macchio to confess his crime, something the Karate Kid will not do without a fight.
the episode: “Gotcha!“ (S.3, Ep.16)
Yet another Drama-fueled cameo! This time Vincent Chase’s brother picks a fight with UFC fighter Chuck Liddell, not the smartest move. Liddell’s acting skills are exactly what is needed even if it is a bit one-dimensional, but that is the point, to play on the brute stereotype. Well, it worked and the dynamic between Drama and Liddell make his cameo something special.
the episode: “Tree Trippers“ (S.5, Ep.5)
Here we have my favorite cameo of the entire series, maybe some of it has to do with shock factor though… Unless Eric Roberts has a reputation I’m not aware of, this one way out in left field. I don’t want to spoil everything for you, but let’s just say “mental journeys” are involved. Again, Drama is the prime facilitator of this cameo which I’ve come to believe is the perfect formula for success.
the episode: “Running on E” (S.6, Ep.4)
Ah, David Schwimmer… This cameo just made sense, actually it’s the same way I feel about Matt LeBlanc on Episodes. After all those seasons on a network show, constantly censored and limited, I’m sure Schwimmer was dying to drop a couple of F-bombs here and there. What better way to do that than HBO? His cameo may be short, but because of who he is and what he represents I will always remember Ross from Friends swearing and being super creepy.
the episode: “Fore!” (S.6, Ep.5)
Like Gary Busey, Jeffrey Tambor was on a few other episodes (one in Season 5 and another in Season 7). This episode stands out above the others for a couple of reasons – three actually:
- more screen time
- the situation
- Jeremy Piven
Piven’s character is going through some issues and Tambor is far from helping. These two create a fantastic dynamic for the episode and will forever make me smile when I think of Entourage.
the episode: “Give a Little Bit” (S.6, Ep.12)
Matt Damon obviously made the list, I mean it’s Matt Damon! In his only appearance on the show Damon kind of acts like a dick, but for a good cause. He’s trying to get money for his charity and Vincent Chase doesn’t really seem to care. With a big name like Matt Damon it only makes sense he brings the likes of LeBron James and Bono with him.
the episode: “Tequila Sunrise” (S.7, Ep.4)
This cameo is great, a little weird, but great. Drama wants Stamos for his new show, but he has to woo him. Obviously, this brings ping-pong into the mix… It’s absurd and hilarious, one of my favorite moments on Entourage. Drama has some of the best relationships throughout the series and his interactions with Stamos is a clear indicator of why.
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