Jimmy KimmelSeason 1 ep 3: “Talk Show”
This is the episode where HBO’s Entourage really hit its stride. In an episode directed by former Seinfeld head writer and Borat director Larry Charles, up-and-coming movie star Vincent Chase (Adrian Grenier) is busy promoting his first starring role in a Hollywood film, Head-On, and casually runs into talk show host Jimmy Kimmel after a boxing match in L.A. Unbeknownst to his older half-brother Johnny Drama (Kevin Dillon), Vince agrees to appear on Kimmel’s show to promote his film, reigniting a longstanding beef between Drama and Kimmel. Meanwhile, the boys are trying to get hooked up with a $100,000 home theater system, and in lieu of paying, agree to some creative late night cross-promotion.
Val KilmerSeason 1, ep 5: “The Script and the Sherpa”
After Vince shacks up with a hardcore vegan he met at the gym, played by the gorgeous former Guess? model Beau Garrett, she helps solve Turtle (Jerry Ferrara) and the boys’ weed problems by referring them to a spaced-out L.A. Sherpa, played by Kilmer in a hilarious homage to his turn as Jim Morrison in Oliver Stone’s biopic, The Doors. Kilmer’s Sherpa grows some of the best weed in the county, and their very Zen smoke session brings the boys luck: Vince’s manager Eric (Kevin Connolly) comes across a gritty screenplay, titled Queens Boulevard, that he thinks is perfect for his only client’s next project.
Larry DavidSeason 1, ep 8: “New York”
Keeping it in the family, the star and creator of HBO’s Curb Your Enthusiasm, Larry David, reveals himself to be one of Ari Gold’s (Jeremy Piven) neglected clients. In typical Larry fashion, he kvetches about Gold not returning his calls after seeing Gold courtside at a Lakers game with Vin Diesel, criticizes Drama’s goatee, and then, when Drama begs for a part on Curb—well, you can guess what Larry says.
Bob SagetSeason 2, ep 5: “Neighbors”
Eric is still dealing with the head games of his ex Emily while Vince begins a flirtation with his beautiful neighbor, Staci. When Vince, Drama, and Turtle head over to Staci’s one afternoon to hang out, they discover that she’s really a high-class madam, and also encounter a robe-clad Bob Saget there, who boasts of having “a house account.” Instead of his nice guy persona from Full House, Saget reveals himself to be an even more debauched version of his standup routine: a foul-mouthed, bong-ripping nymphomaniac who eventually pulls a robbery on Turtle and Drama’s girls.
James CameronSeason 2, ep 7: “The Sundance Kids”
In one of the series’ best episodes, the gang arrives in Park City for the Sundance Film Festival, where Vince’s new indie film Queens Boulevard is premiering. Almost as soon as they touch down, Eric lands a lunch with Harvey Weingard (Maury Chaykin)—a not-so-thinly-veiled version of Harvey Weinstein—and reaches a verbal agreement to have Vince star in Harvey’s indie surfing drama. However, there are whispers that James Cameron will make an appearance at Vince’s screening and, if he’s impressed, will cast Vince in his upcoming blockbuster superhero film, Aquaman. But will Vince land the part?
U2Season 2, ep 9: “I Love You Too”
Vince and crew attend Comic-Con to promote Aquaman, but run into a surly online film critic, played by The Office’s Rainn Wilson, who is threatening to slam the film on his popular site. Eric and Turtle swing into action, convincing a trio of porn stars to sway the critic’s opinion. Meanwhile, Drama proves a big hit at the annual nerd convention thanks to his Viking Quest days, and, after it looked hit or miss for a while, gets an amazing gift from Ari—front row tickets to see U2 in concert, as well as a special gift from Bono that he’ll never forget.
Seth GreenSeason 3, ep 9: “Vegas Baby Vegas”
The entire crew heads to Las Vegas seeking some much-needed R&R from their demanding lives, as well as a $100,000 payday for a Vincent Chase promotional appearance. However, they soon learn that there’s more to the payday than they imagined: Vince must judge a stripping competition. To make matters worse, Ari agrees to go halves on Vince’s winnings at the casino, but Vince soon finds himself down $270,000. Eric has just begun seeing Sloan (Emmanuelle Chriqui), the most beautiful woman in the Entourage universe, but keeps getting taunted by her rumored ex, Seth Green, resulting in an all-out brawl between the two entourages.
Dennis HopperSeason 4, ep 3: “Malibooty”
Eric and Vince aren’t seeing eye-to-eye over Billy Walsh’s current cut of their Pablo Escobar epic, Medellin. While Vince and Billy are convinced they have a masterpiece on their hands, Eric isn’t a fan of the cut, and offers the pair some notes—which makes Billy go ballistic. Vince then ditches his boys on the highway to join a random hottie who takes him to him to the home of her “family friend,” who turns out to be the late Dennis Hopper. The Blue Velvet star and his high-rolling friends convince Vince to bet $100,000 on a soccer game, despite the fact that he doesn’t know anything about soccer, and can’t cover the bet.
Gary BuseySeason 4, ep 8: “Gary’s Desk”
After surviving a run-in with the unhinged Busey in season one, Vince and the boys cross paths with him again when they learn that a $50,000 antique desk that they want to purchase as a gift for Eric—and was once owned by Robert De Niro—is being reserved by Busey. They roll the dice and visit the notoriously eccentric actor at his home, offering him double the money for the desk. Busey counters with an offer that Drama should refuse, but sucks it up for the sake of E and his fledgling business.
Anna FarisSeason 4, ep 10: “Snow Job”
In the previous episode, Eric’s car got rear-ended by Anna Faris’ convertible, leading to some mild flirtation between the two and, after Eric advises her to pass on a bad project, she ends up becoming his second client. During his first day on the job, E must deal with Faris’ idiotic and insanely jealous boyfriend, Dave, whose diva behavior threatens to ruin the actress’ Vanity Fair-like magazine shoot. Finally, Faris gets fed up and dumps Dave, proving that her allegiances lie with Eric.
Kanye WestSeason 4, ep 11: “No Cannes Do”
Vince and Billy’s Pablo Escobar biopic, Medellin, has been accepted as a last-minute entry into the Cannes Film Festival, but a red-level alert has grounded all commercial flights from LAX, threatening the boys’ trip. Ari joins the boys, much to the chagrin of his devoted assistant, Lloyd (Rex Lee) and wife, Mrs. Ari (Perrey Reeves). The super agent milks his contact list and the late director Sydney Pollack agrees to let the boys hitch a ride. Unfortunately, the legendary filmmaker doesn’t end up having enough seats on his private jet to accommodate Vince’s entire crew, so Vince, ever the good friend, politely turns him down. Then, as the boys are leaving, they see rapper Kanye West, who casually re-routes his jet to Cannes for Vince and Co.
Martin ScorseseSeason 5, ep 12: “Return to Queens Blvd.”
Season 5 of the HBO series was relatively devoid of juicy cameos, but the finale more than made up for it. The boys return to their home turf of Queens, New York, where they’re given a hero’s welcome by friends and family. Vince’s mom informs him that she read in the New York Post that Joaquin Phoenix recently left a Gus Van Sant project, but the director is not a fan, and refuses to even consider Vince for the role. After Eric busts his ass to get Van Sant to review rough footage of Vince from his recent film Smoke Jumpers, Van Sant is impressed, but still doesn’t think he’s right for the role, resulting in Vince firing Eric as his manager. Ari then shows up in Queens and puts Vince on the phone with Martin Scorsese. It turns out that Van Sant had passed along the tapes of Vince in Smoke Jumpers to Scorsese, who then offers Vince the lead in his upcoming film adaptation of The Great Gatsby.
Tom BradySeason 6, ep 5: “Fore!”
Turtle and Drama are paired in a charity golf tournament with Mark Wahlberg, the show’s executive producer and inspiration, and New England Patriots quarterback Tom Brady. The pair agree to bet $1,000 every hole, despite the fact that Drama’s golf game—and temper—aren’t up to par. Being a die-hard New York Giants fan, Turtle wants to hate Brady, but despite his best efforts to heckle him, Brady turns out to be a huge fan of Turtle’s squeeze, Jamie-Lynn Sigler, and invites the couple out on a double-date with him and Gisele.
Aaron SorkinSeason 6, ep 8: “The Sorkin Notes”
There’s trouble brewing at Miller/Gold Talent Agency, as Ari’s good friend, TV agent Andrew Klein (Gary Cole), is in danger of being fired by Ari’s partner unless he signs TV writer Aaron Sorkin to the agency. Klein, however, has been in a complete tailspin after recently being dumped by his wife when she discovered that he cheated on her with a fellow agent. Despite Ari’s best efforts, Sorkin refuses to talk to anybody but Klein, and after the fallen TV agent puts his car into his own home and lands in jail, Ari convinces Sorkin to visit him there. Klein breaks down in front of Sorkin, spilling his guts about his divorce, and Sorkin, having gone through a messy divorce himself, sympathizes with Klein, and signs with MGA.
Zac EfronSeason 6, ep 9: “Security Briefs”
A former hated underling at Ari’s agency, Adam Davies, has recently been promoted to the head of a rival talent agency, sending Ari into Terminator mode. Ari informs one of Davies’ most-prized clients, High School Musical star Zac Efron, that Davies had promised Disney a lunchbox with a shirtless Efron in exchange for an extra $5 million for The Rock in Escape to Witch Mountain 2. The shrewd agent then promises Efron a car in exchange for signing with MGA, and orchestrates a conference call between the young star and the dueling agents. And, while telling off Davies, Efron is accosted by an admiring mother at the mall.
Matt DamonSeason 6, ep 12: “Give A Little Bit”
In the season six finale, Vince is cornered by Matt Damon, who then pressures him into donating $100,000 toward his charity organization for kids. Damon paints a hilarious portrait of himself as a charity-obsessed psychopath, and when he runs into Drama, he strongarms him into putting Vince on the phone—“He Jason Bourne'd me!" exclaims Drama—at which point Damon conferences in Bono, who says, “Get off your arse, Vince.” When Damon learns that Vince only cut him a check for $10,000, he corners Vince at the airport—this time flanked by LeBron James—and Vince caves, agreeing to cut a check for $125,000 to the charity. But Damon’s best is saved for the end credits, when he flips out on Vince over the phone after having never received his $125,000 check: “I can’t believe I have a fucking Academy Award and I’m calling YOU back!”
EminemSeason 7, ep 10: “Lose Yourself”
The seventh season of Entourage was packed with celeb cameos—averaging around five or six per episode—but many of them were pure window dressing. In the season finale, there were a whopping 14 celebrity cameos, including Christina Aguilera, porn star Sasha Grey, Dallas Mavericks owner Mark Cuban, and New Orleans Saints quarterback Drew Brees. And, after Vince is dumped by Sasha, he goes on a cocaine bender and crashes a hotel party thrown by Eminem. While there, he sexually harasses Minka Kelly—the real-life girlfriend of baseball star Derek Jeter—and is asked to leave. Vince doesn’t go quietly, saying, “Oh, what are you too mainstream now to fight your own fights, Marshall?” Naturally, this doesn’t go over too well with the fiery rapper.