Ranking Every Single Celebrity Cameo in 'Entourage'

Eight years ago today, our beloved boys from Queens went off the air for the final time. Through 96 episodes and a movie, we vicariously lived through Vince, E, Drama and Turtle as they conquered Hollywood in Entourage, HBO's ultimate wish fulfillment fantasy show. While there were some admittedly forgettable episodes of Entourage, nobody can forget the characters, the cars and the cameos. So in honor of the eight year anniversary of Entourage’s series finale, Complex endeavored to rank every celebrity cameo from every single episode of the show. All 121 of them. To do so we enlisted the only person we could entrust to such a task, JR Hickey the genius behind Oh Yeah, Oh Yeah: The Entourage Podcast, where he breaks down a new episode of the show with a different guest every Monday morning (he’s about halfway through Season 3 at the moment if you want to tune in.)

Some rules: First, JR is only focusing on the show itself and leaving Entourage (the movie) out of it (there might have been 121 cameos in the film alone). Most crucially, he’s also sticking to true cameos: celebrities who played themselves or a bit part for a non-recurring appearance in the show. So anybody who came on and had a major character arc throughout a season was ruled out. Sorry Mandy, Dice and Seth Green.

Without further ado, let’s dive in. Oh yeah!

Let’s get this out of the way: a few aspects of the show didn’t age well. Since its premiere in 2004, times have changed, language has changed and the way people are portrayed on television has changed too. When Lloyd (Rex Lee) was introduced in Season 2, he was a refreshing foil to Ari Gold’s nuclear personality.

Llyod has a nice character development throughout the remainder of the show, but it’s in this late third season episode where we see him used as bait for the predatory, over the top TV writer played by comedian Will Sasso. All the standard lecherous gay stereotypes are used and ultimately Ari Gold saves the day by “rescuing” Lloyd from his would-be client. Just a bad performance and character that doesn’t fit into the Entourage universe at all.

This one was tough because we love Snoop, but this cameo came at the apex of the show just jamming somebody into a scene to say what’s up to the crew and nothing more. He’s used as a plot device to break it to the boys that the Medellin trailer leaked on YouTube, and Vince and E’s reaction is plausible. But Snoop just appearing out of nowhere like an apparition felt contrived. I am going to start saying “Success and nothing less” as a farewell, though.

I guess standing there in lingerie in front of a motorcycle and enduring "compliments" from Brett Ratner gets you higher than him on this list. But not by much.

There were a few problems with this cameo. First, Mrs. Ari leaves Ari for essentially not paying enough attention to her and the family. So she starts dating arguably one of the most popular/busiest chefs in the world? How much more attention is he going to pay her? And the kicker was that the Iron Chef ends up being the person who revealed Mrs. Ari’s first name, which felt like totally unnecessary fan service. Get back in the kitchen, Bob.

It didn’t surprise me that Sloan, while taking one of her many breaks from dating E, would go out with a successful TV actor. What did surprise me was how poorly Galecki’s acting chops translated from CBS to Sunday night cable. Boy Sloan sure has a type doesn’t she?

This subplot about AP selling a dinosaur skull at an auction makes a lot more sense now that we know that he isn’t very good with his money. Although it was a nice homage to Nic Cage paying a quarter of a billion dollars for a reportedly stolen dinosaur skull back in 2007.

Warners exec Alan Gray bringing along a golf ringer in the form of Phil Mickelson during a friendly competition between Ari and Bob Ryan was a stroke of genius. While Lefty’s acting wasn’t Emmy worthy, Ari’s reactions to him being there certainly made up for it.

I almost didn’t include him on the list altogether. Out of the entire cast of cameos here he probably has the most speaking lines in total. The total number of speaking lines that make sense however? Not that many.

He famously told creator Doug Ellin, “Nobody writes Gary like Gary” and didn’t stick to a script in any of his three cameos. His first appearance at his own art show was legendary, his second appearance with the totem pole was forgettable and by the time he asks to paint “on” Johnny Drama I’d tired of him.

One of our first cameos who was taken from us too soon. Boxing with Drama over a previously paid debt for work Drama did on Penn’s house might not seem like a natural fit into the plot in the show. Looking back though, the idea that Drama needed calf implants so he went to Chris Penn’s gym to box him for the money still makes me smile. Nothing’s too absurd for the world of Entourage.

Entourage did a good job of predicting the future: Aquaman, a Ferrari movie, etc. It also was the jumping off point for the careers of certain television stars. Vergara went from the role of “Village Girl” in the Season 4 premiere to the star of one of the most successful sitcoms of the 2000s. The twist of Drama being the one who slept with her over Billy Walsh was one for the ages.

In the Season 7 premiere, Big Dick Nick is bullying Vince into doing his own stunts. Why? Because “This is an important movie for him” and he doesn’t want VInce to come off “Like a pussy.” How many SAG rules does this violate? A convincing but altogether unremarkable cameo.

Speaking of porn...Stan Lee has seen Sasha Grey somewhere before, he just can’t put his finger in it, er, on it. Rest in peace, legend.

Vince asked, and E delivered. ScarJo was the first A-List movie star to appear on Entourage, and she’s the cherry on the sundae of a scene that stands out as one of the more authentic moments of male friendship. However, the performance itself comes across as a bit wooden, as it’s clear she was available for maybe a half hour to shoot her scene.

Why is she in Grand Central Station? Didn’t she say she just got in? And try watching the scene again and not notice her awkward "byeee" at the end of her very not-real phone conversation. Maybe I’m being picky, but hey, I do spend every week dissecting this stuff.

This cameo worked well because it felt authentic to what comedians must deal with all the time when they’re not in New York in LA. I sound like a coastal elite saying that, but the truth of the matter is, in big cities, people respect a celebrity’s privacy more. “Write something funny” should be on every former SNL castmember’s tombstone.

One of the members of Monty Python floating around in the world of Entourage was not something that would have tracked for me as a child. Or for my father as a child, at that. However, the idea of John Cleese being on his fourth or fifth marriage to a ditzy brunette with a bad attitude (and a demo) plus him commiserating about it with Ari was something I thoroughly enjoyed.

Vince appearing on The Tonight Show in the Season 6 premiere signified that he was back on top of the industry. He was about to star in the Enzo Ferrari movie (another nice piece of Entourage foreshadowing) and is all smiles as he recounts his driver’s test on Jay’s couch. Funny enough, The Tonight Show was a month away from transitioning hosts to Conan O’Brien, and Jay was set to do The Jay Leno Show, which lasted all of six months.

The Season 5 finale is a top five episode, namely because the majority of it takes place in NYC and because Martin Scorsese swoops in with a job offer for Vince in the 25th hour. This may go against popular opinion, but I liked the split second Phelps cameo, and here’s why.

At the time, he was coming off the 2008 Beijing Olympics where he established himself as the most dominant and decorated Olympian ever. He definitely could have asked for more screen time. For whatever reason he didn’t and we’re left with a nice nod to him, as opposed to some dopey character or subplot where he convinces us of what we already knew: he can’t act.

A younger Jimmy Kimmel is one of the first cameos that gives the backstory of the crew some depth. He knew Drama coming up together in Hollywood and he owed him a phone call. It was a nice meta touch that had viewers of this very young show asking themselves in Season 1 what was reality and what was entertainment. Who cares, we just knew we were in. And remember, Rufus at Home Video Solutions is the best in the business.

In an otherwise forgettable episode of Entourage (E needs a desk for his new office!), the Queen of hip-hop soul was a refreshing departure from the normal cameo of random Hollywood actor, athlete or rapper. She brought a touch of class, plus she could tell Jim and Jeff, the identical twin agents apart. Hint: Jeff was the one who slept with Jim’s wife.

You have to think back on where Entourage was as a show in 2005. It had just found a new life in on-demand cable viewings so viewership halfway through Season 2 was growing. But its biggest celebrity cameos so far were the iconic Bob Saget performance (which I’ll get to) and a literally phoned-in Scarlett Johansson. The movie industry had yet to put it’s official stamp on the show. Until James Cameron flew in with a helicopter.

Word is the Cameron loved the idea of his cameo so much that he asked creator Doug Ellin for an expanded role in Seasons 2 and 3. While he’s not as good as an actor as some other entries in the top 25, his presence definitely made waves.

Dinklage is barely recognizable without his long hair and massive Thrones beard in this Season 2 cameo. While not a household name when he appeared in "The Sundance Kids," he remains a legend for standing up to Ari’s barside bullying and telling Harvey Weingard to fuck off to his face.

HBO’s known for letting their stars cameo on other HBO shows. You know, keeping it in the family. Little did they know back in 2005 that they were about to have a three-time Emmy winner and the star of the biggest television show of all time on their hands. Confirming that yes, Dinklage is the biggest actor in town, Ari.

Pour one out for this living legend just for the delivery of this line: “Johnny Chase...the monkey boy.”

So technically, Bono’s on this list twice. But since his Season 6 cameo on a laptop screen is utter trash, I’m treating this incredible cameo as a separate entity. The first time we see Bono is in Season 2’s "I Love You Too," when Ari snags U2 tickets for Johnny Drama’s birthday at the Staples Center.

As the story goes, the cast of the show didn’t know if they could get the U2 frontman to wish Drama a Happy Birthday from the stage. It was Jeremy Piven who asked the Irish crooner, and for the entire concert the cast waited with bated breath as cameras were trained on them. When he did finally wish Drama a feliz cumpleanos director Doug Ellin yelled, “Kevin, hug Adrian!” and Entourage history was made. (Read more about filming that scene in Complex's oral history of the series here.)

"Later, B-Squad."

Is it truly a cameo if you’re cameoing in your own life’s story? Marky Mark served as the inspiration, executive producer and driving force behind Entourage and I’d be remiss if we didn’t give him an honorable nod in the top 10. His cameos always brought the laughs and some of the lines he delivered over the years are vintage Walhberg:

“Whoa, it’s the wrecking crew”

“No Ripley’s, we believe you.”

“Oh Drama, you sand baggin’ bitch”

"What language are you talking? What happened? I still don’t know– you’re talking Chinese."

More HBO worlds colliding! Of course Larry David is ticked off about getting uninvited to the Lakers game and replaced with Vin Diesel. I would be too. But, in Ari’s defense, Vin did have the 18-wheeler and the power shades on.

This was a cameo that was the perfect balance of star power and randomness. Like his off-again, on-again show Curb Your Enthusiasm, Larry’s around just long enough in this episode to make you want more. It also brought believability early on in the world of Entourage (this Ari guy’s got some big name clients!) and it gave us another hilarious Johnny Drama scene where he asks somebody for a part in their show.

Don’t ever fuckin’ harass a real client again.

"Gus was kind enough to send me over the rushes of that picture you were in about the forest fires or whatever."

This was another one of those “Holy shit” moments that I’ll never forget reacting to in real time. For years, Vince had said how he’d love to be in a Scorsese movie (well I guess Drama did too but he wants to be in every director’s movie.) At the end of a season where Vince just couldn’t seem to get it together, Marty parachuting in from whatever rooftop he was standing on might have felt a little too convenient, but that didn’t make it any less awesome.

You can’t deny the kind of star power Scorsese has, even as somebody who’s never been much of an onscreen presence. And he comes along at the end of a season that was sorely lacking major celebrity wattage. Vince gets invited to be the lead in Scorcese’s Gatsby, all's right within the Entourage universe and we’re treated to another iconic shot of the boys walking down Hollywood Boulevard, back on top again and turning heads as they go.

"Don’t you fuck my daughters, Vince."

I’m breaking my own rule here because in Season 7, Bob does have a short subplot with John Stamos and Drama. However, it’s his cameo as Vince and the boys’ new next door neighbor which lands him squarely in the top 10. From the Full House DVD box set, to the muffins, to the “Anybody an XBOX guy?” it’s all an incredible, character redefining moment for the actor America had grown to love as Danny Tanner.

Later on in the show’s run, he agrees to sign with Eric’s new agency if he can have sex on his boss Murray’s desk, thus further cementing himself into the legacy of all time Entourage cameos.

I mean the man's most positive, positive, -tive is a negative; It's a mega-negative.

Just five episodes into Entourage, we were treated to one of its most iconic cameos by one of Hollywood’s strangest figures. Val Kilmer agreeing to play the part of the dreadlocked sherpa who gets the boys his “all organic, pesticide free” weed during a weed drought is a creative choice that remains one of the more interesting (and baffling) in the show’s run.

Val absolutely chews up the scenery, and the cast is loving every second of it. Johnny Drama’s reaction to Val recognizing him and saying “I’m a fan, man” has got to be one of the more subtle Kevin Dillon performances early on in the show. Although the idea of needing armed security at your weed farm (as well as the concept of a shortage of green due to a drought) doesn’t age particularly well, this cameo certainly does.

"I see you’re out in your Daddy’s car."

This is the perfect belly laugh cameo from a celebrity because:

50’s GIFabble moment comes at one of the first times Turtle decides he wants more out of life than freeloading off his best friend and girlfriend. Going for a drive in your new Ferrari and getting heckled by Curtis Jackson III feels so much like that dead-on Entourage combination: hilarious and exceedingly cool.

"Put him on the fucking phone, John."

Matt Damon appearing in the Season 6 finale to do some fundraising wasn’t too far of a departure from the comedic skillset he’d recently showcased in Steven Soderbergh’s The Informant! and Ocean’s 13 (remember the nose?) At this point we’ve seen Damon fake “lose it” on countless viral Jimmy Kimmel clips so this wasn’t as much, “Wow I can’t believe Matt Damon is losing his temper on Entourage!” as it was “Wow I can’t believe Matt Damon is on Entourage plugging his charity!”

To land an Academy Award winner at arguably one of the many peaks of his career though is an accomplishment worth recognizing. It’s clear that Damon agreed to do a cameo as long as his plot could be centered around his charity One by One, which felt a little shoehorned in. However, there is no denying that Matt is an incredible comedic actor. The “viralness” of these clips, which are over 9 years old, still stand the test of time, and him hating Vince’s acting is quite believable

"What are you, too mainstream to fight your own fights now Marshall?"

Eminem has, I’m not kidding, four sentences in this episode and it makes for an explosive ending to what’s widely considered one of the more disjointed seasons of the show.

Riding on the success of Recovery, Em capped off his summer by sucker punching the drunk and high Vincent Chase and sending his ass off to rehab, answering Vince’s question about fighting his own fights decidedly. This is another cameo that shows just how high Entourage had climbed. In Season 1, they were begging Hollywood actresses to pretend to know who Vince was. By Season 7, they were getting one of the biggest rappers in the world to throw haymakers at the show’s star in a crowded party scene with hundreds of extras.

"Why don't you stop staring at the guy like you want to fuck him, Turtle?"

By this point in the show, a few small cracks were starting to show. Plotlines had been recycled, new characters were introduced and fell flat (Hello, Andrew Klein) and E and Sloan were in the middle of the second of three “What are we?” phases of their relationship.

And then the boys went golfing with Tom Brady and Mark Walhberg. What struck me, as I’m sure it did to many others watching, was that Tom Brady isn’t just the wooden pretty boy with the dazzling smile plastered across his face that we’d come to expect from NFL interviews. Your boy can act. It might not be exceptionally comedic, which would be tough to do sharing scenes with the likes of Walhberg and Kevin Dillon, but Brady really seemed to be in his element. The spell that Turtle finds himself under in his presence reaches past the screen too, and by the end of the golf event, we want to go to the Bradys for dinner and dessert, too. ​​​​​​Gisele cooks? That’s awesome.

"And after all the talk, all I gotta say is...you’re welcome."

In the penultimate episode of Season 4, the boys plus Ari and Billy Walsh can’t get a flight to Cannes due to a terrorist threat at LAX. After turning down a ride on Sydney Pollack’s private jet because there aren’t enough seats (why?), it looks like they’re stuck in LA. Until Kanye West walks in.

Think back, it’s late summer 2007. In just two weeks, Kanye is releasing his highly anticipated third studio album Graduation (also celebrating an anniversary today.) And not only does he save the day and give everyone a lift to France, he debuts a brand new song from the album over the end credits, one that would go on to be among his best singles. (Ed. Note: we see you, Vener.)

Kanye was the perfect celebrity guest for Entourage because he embodies the generation who watched the show from start to finish. The cliche that’s been attributed to Entourage over the past eight years it’s been off the air is that “It all works out,” in the end for the boys. And that is 100% the case in this instance. But it all working out is what we want, isn’t it? This is a simple show about friendship, life, and having a good time.

Maybe I’ve spent too much time thinking about Entourage (I definitely have) but at the end of the day, there’s something uncomplicated and joyous in watching people you enjoy watching doing things you’d enjoy doing. Like flying with Kanye West on his private jet to Cannes. Welcome to the good life, indeed.