Over the span of eight seasons and a movie, Entourage has had well over 100 cameos. The show has a more eclectic range of cameos than any other, and there is often more than one cameo per episode, ranging from pornstars and rappers to movie directors.
With the show being very of its time in the early and mid-2000s, not many of those cameos have aged very well, but there are others that are hilarious and surprisingly insightful.
10 Best: James Cameron
In one of the best episodes of Entourage according to IMDb, James Cameron makes his first cameo, of many, as an exaggerated version of himself.
Apparently Cameron was so on board with his role that it was his idea to arrive in one scene in his very own helicopter. On top of this, he developed the fictional Aquaman movie in the series, which is one of the movies that Entourage correctly predicted.
9 Worst: Snoop Dogg
Snoop Dogg’s appearance is so minor that he’s one of the celebrities fans forgot were in the show. Snoop Dogg, not being one to turn down a well-paying job, had a cameo in Entourage and gave some forgettable advice to Vincent and Eric.
And while his appearance on the show isn’t outright bad, it seemed forced, awkward, and out of place.
8 Best: Eric Roberts
Eric Roberts is one of the strangest and most entertaining guests in the show, as he convinces Vincent and the gang (including the domesticated Ari) to travel to Joshua Tree with him and get high on "shrooms."
The actor first appeared on the screen by flexing his muscles and telling the gang to punch his abs, and he then gave precious (and maybe terrible) advice to the gang when they were all high.
7 Worst: Bono
Bono made a couple of appearances on the show and both of them were equally as bad. In one episode, Drama was gifted tickets to a U2 concert for his birthday from Ari, and the last five minutes of the 20 minute episode was a performance by the band with Bono pandering to fans in the front row.
The other time Bono appeared it was literally videophoned in, as he was shown on Matt Damon’s laptop trying to convince Vince to donate to charity.
6 Best: Stan Lee
Everybody knows that Stan Lee has done a lot of cameos, and he’s featured in tons of movies and shows outside of the MCU, too. And one of these appearances is in Entoruage, in a strange meeting of the minds when he sits down with none other than the porn star, Sasha Grey.
Lee spends the whole meeting trying to understand where he recognises Sasha from and it’s one of the most innocent and spectacular Lee cameos outside of the MCU.
5 Worst: Kanye West
Back in the days before Kanye West was a self proclaimed genius, called George Bush a racist, and announced his run as president, he was an exciting rapper who enjoyed flashing his cash.
However, this cameo may well be the first evidence of the rapper’s rise to his present-day more ego-fuelled status. In the show, Kanye turns up to save the day, as he lets the gang use his private jet to fly to Cannes, but it’s free of any laughs.
4 Best: Matt Damon
Matt Damon’s cameo in the show is one of the funniest, as it’s so unlike his real life self. Never being afraid to make fun of himself, Damon is restless in his mission to get Vince to donate tens of thousands of dollars to his charity, while he himself is flying around on his private jet.
Though Damon has enjoyed his fair share of cameos over the years, it’s funny how forceful he is here and, surprisingly enough, it’s so unlike any role he’s ever played.
3 Worst: Sasha Grey
Not only was her arc one of the storylines that were never resolved, but Sasha Grey’s appearence in the show is one of the very worst, as it corresponded with the show’s downfall and it led to many of the show’s worst episodes.
Grey does have a lot of charisma when she’s on screen and she does brighten up each scene as the show gets darker, but her role as the person who lures Vince down a path of drugs and wreckless behaviour is cliched, so on the nose, and does nothing for her industry.
2 Best: Bob Saget
Bob Saget is almost like Entourage’s mascot, as he appears so often just to see how the gang is doing. He often lives vicariously through Vince, asking him questions about his love life, but he also gives him life advice, usually about women or drugs.
Though a lot of the advice is ridiculous and unusable, his hilarious attempt to become one of them, even hiring Eric as a manager, is one of the best parts of the entire series.
1 Worst: Brett Ratner
Cameos from directors and producers usually tend to be some of the best, as they usually give insight in to the behind-closed-doors deals that happen so often in Hollywood, but many fans of the show felt that Brett Ratner’s cameo was the worst, emptiest, and most soulless of the show.
In a show in which celebrities play exaggerated versions of themselves, Ratner plays exactly how he is reported to be in real life, by taking advantage of women, using his power to get what he wants, and showing off.
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