At nearly 100 episodes, Entourage is in rare company amongst some of HBO's longest-running bits of original programming—right alongside Sex and the City, The Sopranos, The Larry Sanders Show, Curb Your Enthusiasm, and In Treatment. But unlike nearly every one of those shows, Entourage never enjoyed critical adoration or any attempt to re-appraise its legacy in a better light.
There's a good reason for that. Even in retrospect it's still mostly terrible, a mish-mash of rampant misogyny, casual racism, and glancing homophobia, as well as repetitive plotting. Instead of depicting the glamorous, enviable existence of an actor and his hometown buddies living large and easy in Los Angeles—based on Mark Wahlberg's experiences in the industry—it often felt like a lazy excuse to promote already established stars and leer at attractive, nameless young women.
And yet, there are kernels of insight buried within the bloated, boring beast that is HBO's latest series-to-film revival. In the rare moments when Entourage was at its best, it explored the complex nature of producing a feature film at a major studio, from business-oriented studio executives to overworked assistants, scrambling public relations experts to unheeded accountants, bitter screenwriters to blasé rising ingénues. Basically, whenever Entourage let its guard down, it had a chance to showcase some worthwhile commentary on the entertainment industry, but the rest of the time it mostly just paraded around like an infomercial for an unsustainable fame-hungry lifestyle.
But those fleeting moments of true insight are what kept people coming back again and again for eight seasons. (Well, OK, more than a few of them probably watched for the partying and aforementioned attractive, nameless young women, too.) Here's how to binge-watch your way through the entire series—skipping straight to the good stuff and leaving the navel-gazing behind.
Number of Seasons: 8 (96 episodes)
Time Requirements: A binge of the entire series run would take almost 50 hours. But that's not what we're aiming for here, since that would include a slog through the mostly awful parasitic cycle the show became known for. Instead, we recommend you just watch the best of the best (see below), which is only about 10 episodes/five hours—a light weekend or one intensive Sunday afternoon.
Where to Get Your Fix: HBO Go, HBO Now, Amazon Prime
Best Character to Follow: Ari Gold. Adrian Grenier was a solid, if unspectacular lead as Vincent Chase, "the talent" that kept the series churning, but it's Jeremy Piven's loud, brash, and politically incorrect superagent who provides the most compelling arc over the course of the series. Ari is almost unilaterally cruel to underlings, and especially to his openly gay assistant Lloyd (Rex Lee). But the way Piven struts and bellows, contrasted with his attempts to hold together the semblance of a family life with his increasingly strained wife and growing children, made for a more satisfying and semi-relatable emotional arc.
Moreover, Ari's insatiable ambition never wavers during his rise—from top agent at another man's firm (a devilish turn from Malcolm McDowell which inspired a minor late-career renaissance) to the co-leader of his own big-time agency—and that level of hustle takes more grinding, wheeling, and dealing than any of Vince's serendipitous and laidback strokes of luck. There's a reason Piven won three Emmys for this role—and the only thing Entourage ever won aside from those accolades was for sound mixing.
Seasons/Episodes You Can Skip:
If we're being totally honest here, most of Entourage is skippable. But for anyone looking for a refresher before the movie hits theaters this summer, we've rounded up the only episodes you really need to see below. But there are a few to absolutely avoid at all costs.
Season 2: Episode 7, "The Sundance Kids" In an otherwise reasonable episode about the nature of negotiations over independent film distribution, there's a threesome plot between Turtle (Jerry Ferrara), Drama (Kevin Dillon), and a girl whose attention they compete over that ruins the episode. There are many unbelievable sex plot lines littered throughout the series, but this one might be the stupidest, as the two friends get all gay panicked and prude in the most narratively limiting way possible.
Season 3: Episode 6, "Three's Company" For those of you counting at home, that's not one, but two episodes where the B-plot revolves around characters mulling a threesome. This time it's Eric (Kevin Connolly), his girlfriend Sloan (Emmanuelle Chriqui), and one of her girlfriends. The relationship ramifications are barely acknowledged, so it's basically just titillation, though the scene can't even muster that in any meaningful way.
Season 3: Episode 11, "What About Bob?" Otherwise known as "the one where Turtle hunts for sneakers." Yes, it slightly presaged the rise of limited edition sneaker culture. But seriously, the B-plot is about the least interesting character on the show scrounging for a pair of shoes when he mooches off his rich actor friend for almost everything, only to get bailed out by Vince anyway. Is that something you might be interested in? We didn't think so.
Season 8: Episode 8, "The End" There's a long-running criticism of the portrayal of female journalist characters in film and television. Chris Rock's latest film Top Five kicked things up again when Rosario Dawson's character hooked up with the subject of her article. That's the same basic problem here, as Alice Eve's Vanity Fair writer goes from penning a scathing profile of an out-of-rehab Vince to absconding to Europe to get married. Entourage began as a fantastical satire of the entertainment business, but by its end, it was pure hetero male gaze fantasy. The trailer for the feature film coda makes it look like not much has changed since this final iteration, which isn't an encouraging sign.
Seasons/Episodes You Can't Skip:
Season 1: Episode 1, "Entourage" It's the pilot, so you can't really skip it, since it introduces all the major players and where they start. Vince is a rising young actor; Johnny is the has-been actor and older brother; Eric is the wannabe-entertainment player and hometown best friend; Turtle is the ultimate hanger-on and designated weed carrier; and Ari is the agent and connection to the broader entertainment world.
Season 1: Episode 6, "Busey and the Beach" Early in its run, Entourage didn't just bring in celebrities for glorified cameos that felt like branding instead of character additions—it let those celebrities get weird. Val Kilmer played a "sherpa" during this season, and Gary Busey contributed to his public persona as a professional crazy person in this episode where he plays himself as an eccentric painter, offended by Turtle. It's also one of the first instances of Ari's insatiable competitive attitude, as he mercilessly flays a former assistant who has become a competing agent at another firm.
Season 2: Episode 6, "Chinatown" Before it got lost in a sea of endless parties and celebrity romances, Entourage had time to actually be a comedy about some of the dirty little secrets of Hollywood. Case in point is this episode, which puts Vince in a Chinese energy drink commercial for $500,000. (E and Vince both note that's more than their respective fathers made in their entire careers.) Yes, there's a gratuitous seduction scene—though the stuntwoman played by Bai Ling isn't as terrible here as she is in *Lost'*s worst episode, "Stranger in a Strange Land." But the resulting faux commercial, complete with Johnny Drama cameo, is one of the best send-ups of how celebrities used to be able to make absurd amounts of money internationally without damaging their American critical reputation—before the rise of YouTube and other video services that now preserve those embarrassments in perpetuity.
Season 2: Episode 13, "The Exodus" Ari's brief fall began much sooner than Vince's eventual downturn, as he butted heads with Terrence McQuewick (Malcolm McDowell), conspiring to peel a group of agents away and start his own firm. When he's betrayed, the plan goes up in smoke, and Ari's embarrassing exit, as he attempts to save face, is an important humbling moment for the character. He rages against the whole experience, but in the end, all he can do is get drunk, listen to Lloyd, and dance in the street with his wife.
Season 3: Episode 2, "One Day in the Valley" Vince gets his Almost Famous moment at a house party in the San Fernando Valley, but this episode is mostly notable for the way it got in on the ground floor as superhero box office bonanzas were kicking movie studios into a frenzy. It’s after the success of Spider-Man but before Marvel figured out how to be a movie studio, so the hand-wringing over box-office numbers and a southern California heat wave affecting screenings actually comes off as both prescient and quaint.
Season 3: Episode 12, "Sorry, Ari" On one hand, the endless series of identical presentations that Vince and his friends endure while looking at other agencies is one of the best recurring motifs to critique the business in the entire series. On the other, it's incredibly dispiriting when Vince walks into Ari's firm, ready to be won back, and sees just another cookie-cutter presentation marketing the actor as a big-name brand. This is one of the only times where the emotional bottom drops out of the show in a surprising way, and it actually hurts to see the team split up in such a gut-wrenching fashion.
Season 4: Episode 12, "The Cannes Kids" One of the major side-effects of the ubiquitous criticism that nothing ever happened on Entourage was that big things tended to happen only in season premieres and finales. That's largely true of the fourth season as well, which deals mostly with the run-up to the premiere of Medellín, a self-produced passion project about Pablo Escobar directed by Billy Walsh, the insanely anti-corporate capital-A Artist based in part on Vincent Gallo, Quentin Tarantino, and writer Rob Weiss. Entourage was often better at the unexpectedly colossal failures than it was at rewarding the merry band of sycophants around Vince with improbably escalating success. That's why this finale works so well, as a lackluster Cannes debut undercuts the bloated, self-important attitude of everyone involved—with a great final kicker from the show's Harvey Weinstein stand-in.
Season 5: Episode 5, "Tree Trippers" Maybe we're just big on episodes where twisted Hollywood former bad-boy actors show up, but Eric Roberts is fantastic in this chapter of Vince's career redemption arc, ushering the group out to Joshua Tree to trip on illicit substances. The whole experience, which harkens back to that visit to Val Kilmer's "Sherpa" character, only with a darker twist, leads to the hallucinogenic moment that convinces Vince to take a part in Smokejumpers, the prototypical meaty supporting role that will soothe the ills of *Medellín'*s direct-to-DVD disaster.
Season 5: Episode 11, "Play'n with Fire" Based in part on Mark Wahlberg's time filming The Perfect Storm with George Clooney and German director Wolfgang Peterson, the fifth-season Smokejumpers arc was one of the most ambitious things the show ever attempted. Stellan Skarsgård is great as the thundering and demanding director who wants Vince off the film, and any plot that involves Dana Gordon (Constance Zimmer) is a good sign. Entertainment about art and artists doesn't usually tip a hand as to whether someone is a genius or a hack, but this season of Entourage attempted to dig into Vince's craft, how he approached that work, and whether he could live up to his own distracted ambitions.
Season 7: Episode 10, "Lose Yourself" After a rather rote sixth season, the penultimate year of the show put Vincent Chase through a "fall from grace" storyline that sees him date Sasha Grey and descend into drug abuse that threatens to derail his entire career. The final season provides the requisite redemption, since America is a land of second chances, but it's almost entirely uninteresting as it goes down the line to reward all the characters with happiness. That's why this season finale—which leaves Vince's career, his friends' financial dependence, and Ari's marriage all hanging in the balance—is perhaps the last good episode of the series.
Why You Should Binge:
Entourage as a whole will take too long and inflict undue punishment on unsuspecting viewers. But it's still an important show in HBO's legacy, a comedy along with Sex and the City which balanced out all the antihero dramas. It's a great example of how the entertainment industry cannibalizes itself in order to present a glossy, alluring, and just barely self-effacing image to the public. The upcoming film version will either prove that the show has an enduring but largely critically ignored legacy, or it will doom it to the mysteriously long-running reject pile along with Arli$$.
Best Scene—Eminem Beats Up Vincent Chase:
After a season-long spiral into drug addiction and personal despair, Vince winds up at a party, harassing Minka Kelly and pissing off an initially helpful Eminem, leading the Detroit rapper to wind up and sock Vince in the face, acting as the gleeful audience surrogate. It's the series' single most cathartic rebuke. There's a possibility that, out of context of the entire insufferable run, this moment won't play as gloriously as it does after watching the whole series, but it's still entertaining as hell to see Marshall Mathers knock Vincent Chase out again and again. Even aside from that hate-watching instinct, the moment Johnny Drama realizes he can't save his little brother from an ass-whooping, leaving him helplessly screaming into a crowd, is one of the last times the series mustered up real drama.
The Takeaway:
Fame ain't all it's cracked up to be, maybe?
If You Liked Entourage You'll Love:
Here's another section that doesn't quite vibe with this somewhat truncated series recommendation, but if you're in the mood for more entertainment satire or entrepenurial spirit, there's HBO's unfortunately short-lived How to Make It in America, which had a great cast including Lake Bell, Luis Guzmán, and Kid Cudi. Give that one a spin.
