During its eight season run, HBO’s Entourage took us on a whirlwind tour of Vincent Chase and his closest friends’ careers in Hollywood. The show made the famous entertainment capital every bit as glamorous as we hope and as crazy as we’d like to remind ourselves that it is.
But there was also something that felt attainable about the whole thing, especially with the setup of these average NYC borough kids and their day-to-day life in a new town. One of the most critical parts of that engagement was seeing celebrity guest stars casually appear on-screen in each episode.
Here are some of the celebrity cameos that might have come and gone too quickly to remember specifically. And a few cameos that defined their episodes. Here are 15 Celebrities You Forgot Appeared On Entourage.
And a quick warning for those of you with sensitive ears, some of the clips below are not family friendly.
14 SCARLETT JOHANSSON – SEASON 1, EPISODE 8
This was way before Scarlett Johansson had become Black Widow in the Marvel Cinematic Universe. She had made a name for herself with films like Lost in Translation, but by 2004, Johansson was barely out of her Dawson casting phase, yet she was still big enough to catch Vinny Chase’s eye. He keeps urging E to get him in touch with her.
At the end of the season 1 finale, E hands Vince his cell as he’s about to board a plane for New York. It’s Scarlett! Turns out they’ll both be in New York and she suggests a breakfast date, to which Vince agrees, of course. Vince took it as pretty good sign that E could work this out as his manager. One has to wonder how the show might have treated Scarlett Johansson’s cameo if it had been after Black Widow, or even Lucy.
13 SARAH SILVERMAN – SEASON 1, EPISODE 3
The episode “Talk Show” was packed with celebrity cameos, especially for any viewers familiar with boxing. The episode opened with Vince and the gang attending a boxing max between Vitali “Dr. Ironfist” Klitschko and Corrie Sanders. At an afterparty, Vince agrees to appear on Jimmy Kimmel Live. Each of the crew gets into their own awkward situations in the prep rooms and green rooms, but Ari has a chance run in with Sarah Silverman.
By Entourage’s first season, Silverman had appeared in several TV shows and established her quirky comedic persona. Ari’s poorly worded pitch leads Silverman to believe he’s trying to get in her pants, especially since she takes Krav Maga classes with Ari’s wife. But Ari quickly, albeit brashly, recovers and makes it clear he wants to sign her on with his agency. In return, Silverman helps to get Ari through to the green room.
12 PETER DINKLAGE – SEASON 2, EPISODE 7
Peter Dinklage had several memorable character parts before he became Tyrion Lannister, including recurring appearances on Nip/Tuck, Life as We Know It and I’m With Her. Not to mention, he got to throw Will Ferrell onto a conference table in Elf. In 2005, his most recent movie had been The Station Agent. Dinklage gets into a bit of an awkward conversation with Ari springing off that very movie.
A lot of Dinklage’s early work didn’t shy away from self-conscious humor based on his dwarfism in Hollywood. And Ari, being who he is, can’t help but work in some puns based on size. He says he could have signed Dinklage on for Bad Santa, but Dinklage says he specifically passed that up, presumably referencing Tony Cox’s role in the movie.
“You’re one of the biggest actors in this town Peter”
“What is that a play on words or something, d**k head?”
11 AMANDA PEET – SEASON 2, EPISODE 1
Amanda Peet’s most recent claim to fame is another HBO comedy-drama, Togetherness, which premiered in 2015. She’s also married to Game of Thrones co-creator David Benioff. She guest starred in the season 2 premiere of Entourage. Prior to that she had roles in movies like Something’s Gotta Give, Identity, The Whole Ten Yards and the TV series Jack and Jill.
E is setting up Vince’s connections again after his smaller scale movie from the end of last season, when he bumps into Vince’s publicist Shauna, accompanied by Amanda Peet. Peet doesn’t recognize E, but shows much more interest when Shauna mentions that he’s Vincent Chase’s manager. Though without a company or a business card, he doesn’t hold her interest for long, nor does he impress Shauna.
The Granddaddy playboy himself, and also a former journalist for Esquire and WWII veteran. Hugh Hefner and the allure of his Playboy Enterprises guest starred in season 2. Unfortunately, Drama made a bit of a fool of himself the last time he was at Hefner’s zoo, letting loose a whole load of chimpanzees on one of their spokespersons.
When they’re stopped at the gates, Drama gives up, lets the rest of the gang head inside and starts walking home. Turtle finds a way to sneak Drama back in, but he ends up causing a scene with the Ralph Macchio, with each accusing the other of setting the monkey’s loose. But then they both remember the third guy who actually busted the cages in their drunken stupor. Hefner shows up, playmates in tow, kicks the true offender out for life and reconciles with the Chases.
It was an appropriate top off to one of Entourage’s most gloriously entertaining scenarios.
10 MARTIN SCORSESE – SEASON 5, EPISODE 12
One of the most celebrated directors of modern cinema, the Italian American filmmaker Martin Scorsese appeared in the season 5 finale. Things had been a bit rough with the gang in New York, with E and Vince getting into a fight (again).
Vince and the gang are hanging out in Drama’s newly christened bar when Ari walks in with that unmistakable smug look. Vince had just been dropped from a major dramatic role as a forest firefighter, but it seems that another director had seen the b-rolls and wants to bring Vincent onboard. That director is none other than Martin Scorsese. He wants to shoot a modern reimagining of The Great Gatsby in the Upper West Side with Vincent as Nick Carraway. Vince tries to maintain his aloof Hollywood bigshot act over the phone, but he’s obviously excited. Landing the part also leads to E making up with Vince and the gang.
9 SOFÍA VERGARA – SEASON 4, EPISODE 1
Season 4 opens with Vince and the gang arriving on location in Colombia to shoot a film called Medellin with the inspired new director Billy Walsh. Right away there are “creative differences” with Walsh and E, who’s producing the movie. Walsh is so impassioned about this project that he threatens to drag Turtle into town and sell him as a drug mule when his cell phone goes off in a production meeting.
Sofía Vergara shows up as a fictional potential cast member, not as her Hollywood self. Every one of the boys is agog at her, especially the director. The problem is that he’s running the show, and when he takes his sweet time chatting her up, the whole production comes to a standstill.
“I only have a couple of scenes in the movie. Film! So I don’t understand why the director wants to have all his meals with me.” Vergara has since grown to play up her attractive qualities along with a sharp tongue as part of her public persona. She’s also starred in the TV show Modern Family since 2009.
8 SNOOP DOGG – SEASON 4, EPISODE 5
By season 4 episode 5, Medellin has been making rounds at the Cannes Film Festival. The boys take it as an excuse to live it up on and make purchases of questionable affordability.
Vince and E are out and about in the morning when they bump into Snoop Dogg, who congratulates them both of the new movie. And the new trailer? Vince and E don’t question, but apparently a trailer was released on YouTube without their knowing. Even though Snoop says the trailer makes Blow look like Romper Room, this wasn’t the plan.
Walsh is right in the next room that Vince and E are headed towards, and he is convinced that E leaked the trailer. They trash talk each other until E tackles Walsh into an adjacent dinner table.
7 ALEX RODRIGUEZ – SEASON 8, EPISODE 7
He started out with the Mariners in 1993, switched to the Rangers in 2000 and was traded to the Yankees in 2003. With a new nickname, A-Rod, Rodriguez’s stint in the Yankees would see him become one of the most famous and successful baseball players of all time.
So how does Entourage include him for a cameo? Turtle is trying to win over investors for this new restaurant he’s starting up, mostly athletes, but he’s got no luck. Things could be looking up when an “Alex” calls him, but he’s got some bad news. Avion Tequila, which Turtle just sold his stock in, went public. He stood to make million but instead he just blew it. It was an unceremonious cameo delivering a plot point, but it was believable, especially for the mention of teammate Mark Teixeira.
Fortunately for Turtle, Vince held on to his stock in Avion and bought Turtle's before he went public, meaning that he'll be able to keep the money.
6 ZAC EFRON – SEASON 6, EPISODE 9
The then poster boy of Disney’s High School Musical franchise is pretty big money, and thus he becomes the focus of Ari’s talent hunting coup for the episode. He slips to Zac that his current agent Adam Davies promised Zac would do a shirtless lunchbox, leveraging him in other words. Lloyd gets Zac, Ari and Davies all on a conference call in which Zac tells Davies in no uncertain terms that he’s fired. Ari agrees to give Zac a signing bonus “with four wheels and leather seats.”
The funniest part about the scene is that while the conference call is going on, Zack is getting fawned on by a young girl and her mom. He signs an autograph made out to Laurie. When he addresses the little girl as Laurie and says “it was nice to meet you,” The mom says, “I’m Laurie!”
The mom even approaches Zac again to let him know she would buy that shirtless lunchbox.
5 MALIN AKERMAN – SEASON 3
One of the more stand out actresses to play an original fictional character in season 3, Malin Ackerman shows up as Tori. She’s the smoking hot best friend of E’s long time lady-love Sloan. When the two of them crash the gang’s guys night out, Sloan calls E at the end of the night to tease him that Tori wants to have a threesome!
If any show could conquer the inevitable awkwardness of getting one of its main characters into a threesome, it’s Entourage. It seems to go well enough, except E wakes up cuddling Tori instead of Sloan and he’s got feelings for her. He’s so conflicted about it that he tries to talk to Tori alone and apologize, but he only makes the situation more awkward.
But not as awkward as when Tori hints to Eric alone that she’d like to try a threesome again, with “less rules.” In the end, E’s conscience wins out and nothing more happens between the three of them, or E and Tori.
4 BOB SAGET – SEASONS 2, 6 AND 7
Bob Saget brings his well-known brazen adult humor to his cameos throughout the series. In season 2, Turtle and Drama are hanging out at his place with some premium Columbian grass. Drama, as always, tries to play up his laundry list of acting credits, asking Bob if he remembers an appearance he had on Full House. Bob doesn’t remember.
He appears again in season 6 for some seriously show-stealing shenanigans. E and Scott are trying to sign Saget on, with Saget crudely rebuking Scott’s salesman like pitch. He bullies Scott out of his own office and then gives E a proposal. He’ll sign if he can have sex in Murray Berenson’s office. E is flabbergasted. Berenson puts on an incredulous, sanctimonious show, talking about how he built his agency from the desk of his very office, and that he won’t let Saget turn it into a whore house.
But he was just screwing with E. It’s all good. His ex-wife decorated the office anyway. Pretty weird first day on the new job for E.
3 VAL KILMER – SEASON 1, EPISODE 5
Vince and the Gang hear about this seriously hardcore West Coast pot grower called the Sherpa, played by Val Kilmer. Yes, Joel Schumacher’s Batman Forever Val Kilmer. But he’s hardly recognizable with the epic mane and the shades. The guy’s got goats and ducks and cows roaming the yard of his Bel Air property. Not to mention entire greenhouse stalks of the plant towering over stacked bags of product ready to go.
The crew seems to be settling in on bags and ottomans just fine. Sherpa waxes philosophical while passing the bong. E, the most practical minded of the crew, asks the Sherpa about what if he’s ever busted. He brushes it off with more puns and rhymes. Suddenly, E’s phone starts ringing. Sherpa and a house guard draw on E right then and there. The tonal whiplash is almost as big for the viewer as it is for E.
Sherpa lets E answer his phone. Certainly one of the earliest and weirdest cameos the show ever had.
2 GARY BUSEY – SEASONS 1, 2 AND 4
For whatever reason, Gary Busey’s persona on Entourage is that of a possessed, enlightened artist, constantly roping the gang into his experimental art projects. The first time we see him in season 1, he’s introducing a mural piece that’s not much more than blue and white polka dots, calling it “emotional confusion, like running through a corn field naked and backwards at midnight.”
Turtle certainly doesn’t endear himself to Busey when he accidentally knocks over one of his pieces at that same exhibit. Turtle does the mature thing and tries to apologize to Busey at a beach party later, only to get threatened with a snapped sternum, and gets a bucket of sea water dumped over his head.
Later in the series, he wants to do body paint photography with Drama. He even chants as he passes over Drama with chaotic brush strokes. “This is statement of enlightened photography. The unseen faces of the familiar.” Probably one of the most colorful recurring guests Entourage ever had.
1 STAN LEE – SEASON 7, EPISODE 5
Stan The Man! Vince is in talks to play another superhero for a major studio pic, Air-Walker. It’s a whole episode packed with recognizable stars such as Jessica Simpson, Mike Tyson, Aron Sorkin and even Bob Saget again. By this point in the season, Vince is getting on pretty well with porn star/girlfriend Sasha Grey. With everyone else tied up, she’s the only one who accompanies him to the meeting with Randall Wallace, the director, and Marvel legend Stan Lee.
Stan is all too happy to meet Vince and Sasha, especially Sasha. After all, she looks very familiar. Stan may not have admitted he recognized her, but according to phone conversations after, between Vince and E, Wallace was none too impressed. Stan Lee was arguably the icing on the episode’s veritable cake of guest stars. It was almost enough to distract you from the divisions brewing in the gang.
Were there any other guest stars in the Entourage series that deserve a call forward again? Let us know in the comments!