The 25 Best Episodes Of "Entourage"

In honor of Sunday night's series finale, we count down the HBO hit's finest moments.

Entourage
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Entourage

This Sunday night, HBO's Entourage, one of the best bro shows of all time, will air its series finale. With the exception of a hopeful feature film (fingers crossed), it's all over for the boys from Queens. Movie or not, it's not like we're being left empty-handed. Entourage has given us eight years' worth of entertainment, some of them great, others not so great, yet all watchable and suitable for kicking back and living the fast life vicariously through movie star Vincent Chase (Adrian Grenier) and his hometown homies.


When it comes to the best season, there's really no question: Season Two was an instant classic. The series may have never topped year two, but each season has not been without at least one episode that will live on in HBO re-runs for years to come. Unbelievably hot women, cameos from just about all of the industry and then some, enviable toys and riches, and of course, bromance; we're going to miss it all. Reflecting upon all eight seasons, here are our choices for the 25 Best Entourage Episodes. 

25. "Bottoms Up"

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Season: 7

Air Date: August 1, 2010

Entourage's take on anal sex naturally was the first episode to feature recurring guest star Sasha Grey. But, really, this episode could've been awful and it still would have made this list for the line "Vagina is my third favorite hole" alone. Delivered by Johnny Drama (Kevin Dillon), of course.

24. "Whiz Kid"

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Season: 8

Air Date: August 14, 2011

In a perfect world, all of season eight should have been eligible for this list, but, unfortunately, that isn't the case. This was definitely one of the most entertaining of this year's bunch, though, and one that fortunately signaled the end of the season's slow start.


Co-written by Turtle himself, Jerry Ferrara, "Whiz Kid" finds the gang banding together to help Vince pass a drug test he's sure to fail since he took a puff of weed days ago to prove he's not really an addict. The solution is hilarious and Vince-, largely considered the least interesting of the bunch, is surprisngly compelling in his dilemma, plus genuinely funny; Grenier's delivery of "I'm wearing a fake cock" to a stunned E is golden.

23. "The Bat Mitzvah"

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Season: 2

Air Date: August 7, 2005

Anchored by the arrival of a little family called the McQuewicks—you know, Terrance and Sloan—this episode finds Vince and Eric (Kevin Connolly) at odds over Vince's worsening simp affair with Mandy Moore. Would Vince really bag Sloan to spite Eric? Sorry, Vinny, but this is one dime that isn't wowed by a SAG card.


On the Ari Gold (Jeremy Piven) front, he's starting to fear that boss Terrance is about to swoop in and take Vince from him, similar to the Bill & Ted premiere when he said "I'll take Ted...you take the other guy." Sloan (Emmanuelle Chriqui) had us captivated from her very first appearance, but the episode's true scene-stealer is Melinda Clarke, namely due to her fearless diddy-bopping at Ari's daughter's bat mitzvah.

22. "ReDOMption"

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Season: 5

Air Date: October 12, 2008

In this one episode, we got the return of two clowns and one antagonist from the third season who were well received, but whose storylines were exhausted. All things considered, "ReDOMption" should've been too much, but by its end one character was dead, another, Dom (Domenick Lombardozzi) was headed for jail after possibly alienating his family forever, and... Well, Bob (Martin Landau) was still Bob.


We never thought we'd end up feeling sorry for Dom, the gang's would-be fifth member and perennial screwup. The one-two punch of Dom's wife leaving him for getting arrested again and the death of Alan (Paul Ben-Victor), the Warner Bros. studio head who hated Vince's guts, was shocking and way more effective in achieving a rare, somber tone than the sloppy suicide episode from this year's final season, "One Last Shot." Hell, the subplot with Turtle acting as Drama's new assistant even ends on a dour note. Refer critics who claim that Entourage is substance-free to this one.

21. "The Scene"

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Season: 1

Air Date: August 29, 2004

Damn, can you believe crazy director Billy (Rhys Coiro) has been on this show since year one? In "The Scene," he makes his entrance in a grand fashion, hilariously predicting Eric's future transformation into a suit then adding a decidedly homoerotic scene into Vince's project. Actors who have gone gay: Will Smith, Robin Williams, Leonardo DiCaprio, Al Pacino, and...Vincent Chase?


Meanwhile, Drama spends the episode holding on to a wad of residual cash from Viking Quest that he vows never to spend...until he bags a stripper who's too worried about her rent to party: "I got your rent money right here." No wonder this guy was broke for three seasons.

20. "Tree Trippers"

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Season: 5

Air Date: October 5, 2008

Vince is in a career crisis, so the gang turns to the O.G. actor Eric Roberts to take them on a vision quest at Joshua Tree, powered by some grade-A shrooms. There's a lot to like here, such as Lloyd (Rex Lee) and his boyfriend's gay bash inside Ari's home while his family is gone, Roberts' unexplained venom towards Ari ("We could just kill him out here and no one would know"), and Eric's shroom-induced muteness.

19. "The Resurrection"

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Season: 3

Air Date: May 13, 2007

You rarely find yourself feeling sorry for these guys, for the simple reason that the Entourage crew members almost always get everything they want. That is, except for Drama, whose pathetic career spiral is often played for laughs.


So as Drama seems to be getting teed up for yet another public failure with his new TV show, nothing was more surprising than the decidedly unfunny shot of him driving off into the night crying. After three and a half seasons of bad luck, nothing was more rewarding than Drama waking up in his Lincoln to the boys plus Lloyd calling to tell him his premiere was a hit. Victory!

18. "Scared Straight"

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Season: 6

Air Date: September 27, 2009

Gearing up for the terrific Season Six finale, E acknowledges his age and experiences something we can all relate to: the fatigue and health hazards of sleeping around town and the desire to settle down. Getting with one of Johnny Drama's conquests would give anybody pause. And speaking of Drama, laughing at his failure stops being funny and gets real in "Scared Straight": this time an audition with the rude casting team behind CSI sends him into a serious panic attack.

17. "Malibooty"

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Season: 4

Air Date: July 1, 2007

There are very few unwatchable episodes of Entourage, mainly because it has a fully functioning ensemble cast. The "A" story may sometimes be stagnant, but you can always count on the comedy duos of Turtle & Drama and/or Ari & Lloyd to salvage the episode.


So even though Vince spends this one mostly just hanging out with Dennis Hopper while he and Eric beef over Billy's cut of Medellin, "Malibooty" is still a classic thanks to comedy team number one's ridiculous dalliance with two '90s party girls that Drama used to know.


Great one-liners are abound here, from Drama's insistence that Turtle's date gives "the best rimjobs in L.A.—just ask Chuck Sheen," or guest star Lisa Rinna's deadpan delivery of "Whaddya say we get out of here and go fuck?" Plus, Ari to Vince, re: Eric's subterfuge: "Do you know that your man broke out of the oompa-loompa factory, and is up to no good?"

16. "Sorry, Harvey"

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Season: 4

Air Date: July 8, 2007

Though some of Entourage's fourth season was uneven, "Sorry, Harvey" fires on damn near all cylinders. E must tell Harvey Weingard (Maury Chaykin), a notoriously unhinged and scary producer that he and Vince are backing out of a partnership they already agreed to (again), but he repeatedly chokes after witnessing display after funny display of the man's insanity.


Elsewhere, Drama's vanity is on full blast as he ropes Vince into taking out the mayor of Beverly Hills so his condo will be annexed into the zip code. Of course, E and Harvey (R.I.P. Maury Chaykin) end up where Vince and Drama are and shit goes down, with a cherry on top thanks to the all-seeing eye of TMZ.


Surprisingly it's pinch-hitter Ari who gets saddled with a pretty flat plot involving M. Night Shyamalan. But M. Night's known for flat plots these days, anyway.

15. "The Day F*ckers"

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Season: 4

Air Date: July 29, 2007

In this low-key but still memorable episode, the Chase brothers bet on who could get laid the fastest in 24 hours: E and Turtle? It becomes less about the competition, however, and more about Eric's awkwardness when it comes to casual dating. In addition, "The Day F*ckers" also features the fourth season's only Sloan appearance and a terrific, laugh-out-loud sight gag at the end.

14. "Seth Green Day"

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Season: 5

Air Date: November 9, 2008

Entourage's best celebrity guest star pops back in for an encore appearance as Eric's nemesis, this time with Bow Wow in the mix. There's also the hilarious sight of Ari crashing a luncheon for successful business women, which ends up just as wonderfully profane as one can imagine.

13. "Three's Company"/"Strange Days"

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Season: 3

Air Date: July 16, 2007; July 23, 2007

E, Sloan, and guest star Malin Akerman have a threesome—enough said. No cheat, it really plays like a two-parter as the aftermath of "Three's Company," seen in the following episode, "Strange Days," has funny and awkward results for Eric. There's also assorted hilariousness involving Ari, Mrs. Ari and enemies Terrence and Melinda Clarke, in one of her hilarious guest appearances as Terrence's random trophy wife. But really, who wouldn't want to marry her?

12. "Play'n With Fire"

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Season: 5

Air Date: November 16, 2008

In "Play'n With Fire," Turtle finally gets his day, spending a magical 24 hours with Jamie-Lynn Sigler (he even tells her his government!) and Vince's battle with the Smokejumpers director erupts into one of the more absurd—in a good way—and ultimately somber climaxes Entourage has ever seen.

11. "I Love You Too"

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Season: 2

Air Date: July 31, 2005

Entourage is at its comedic, satirical best when it's mocking or integrating events and practices in Hollywood that are business-as-usual to industry folk, so of course at some point the gang had to venture to Comic-Con San Diego, and of course Drama ends up being a nerd hero there.


The friction between Vince and Mandy Moore continues to unfold and suprisingly isn't annoying; meanwhile, Turtle enlists three porn stars to help Vince get a dickhead journalist (Rainn Wilson) off his back. Did we mention said porn stars are at Comic-Con promoting something called "Pussy Patrol?" Yeah, *dead.*

10. "Sorry, Ari"

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Season: 3

Air Date: August 27, 2006

"Sorry, Ari" brings more satiric greatness as Vince and the gang go shopping for new agents, only to be disillusioned by the detached corporate-ness of it all ("Microsoft! Coca-Cola!...Vincent Chase!"). Drama may be the family's resident failure, but he's also the more experienced (he has a fishbowl full of agency business cards) and it's up to him to talks some sense into Vince and help his little brother realize that no other agency can duplicate Ari's true loyalty.


Alas, miscommunication is the death of all relationships. The episode's intelligent look at the Vince/Ari friendship is enough to help us ignore the fact that the impulse to fire him comes out of nowhere and is a bit overreactive. It's one hell of a mid-season cliffhanger, though.

9. "The Sundance Kids"

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Season: 2

Air Date: July 17, 2005

This second season gem featured the first appearance of crazy Harvey, a predictable but still very funny subplot involving Turtle, Drama, and the gang's hot driver for the Sundance Film Festival, and a risky gamble by Vince and E that pays off in landing the biggest fish of them all, a film to be directed by James "Titanic/Avatar" Cameron.

8. "Neighbors"

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Season: 2

Air Date: July 3, 2005

The craziness of Bob Saget is a well the show visits often, but the writers were never able to top the genius of his first appearance as Vince's neighbor in, yes, "Neighbors." The ever-oblivious Vince has no idea who Saget even is, yet they have more in common than they know regarding some other neighbors, i.e. the high-class hookers down the block.

7. "The Script And The Sherpa"

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Season: 1

Air Date: August 15, 2004

There's a weed drought in L.A. and, what's worse, Vince is letting his new, earthy girlfriend voice her opinion on career strategies, much to Eric's chagrin. Entourage started out with a certain offbeat quality it never quite maintained after the first season—for better or for worse—but it's on high here when the guys visit a Sherpa, played by an unrecognizable Val Kilmer, the first celeb to show that special guest stars could do more than just play themselves for cameos.

6. "Give A Little Bit"

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Season: 6

Air Date: October 4, 2009

"Give A Little Bit" is a surprisingly sweet episode and one that significantly advances the plot after a season that mostly stood still, wrapping things up so nicely that some feared it was actually the series finale.


It's an exhibition of everything the show does well: celebrity cameos (Matt Damon takes aim for best Entourage guest, over-the-top Ari scenes (the paintball sequence is so awesome you can ignore the fact that he'd realistically be facing about a dozen lawsuits), Hollywood high stakes (Drama vs. the audition...again), and awesome music selections (Jay-Z's "In My Lifetime (Remix)"). Oh, and genuine romance. Act like you didn't crack a smile when Eric jumped back off of the plane.

5. "Aquamansion"

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Season: 2

Air Date: June 19, 2005

Living the dream vicariously through the foursome was never more entertaining than in "Aquamansion," which saw everyone eagerly getting ready for a pajama party at the Playboy Mansion.


Turtle is out to score the freshest pajamas, Drama fights to lift his "life-long ban" from the mansion, crossing paths with original Karate Kid Ralph Macchio and nemesis Pauly Shore, and Vince doesn't want to give up his artistic credibility to do a superhero movie. That is, until he sees Marlon Brando's gorgeous mansion on the market. We still laugh at the sad, defeated Johnny Drama's walk of shame, draped in a silk night robe.

4. "The All Out Fall Out"

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Season: 5

Air Date: September 21, 2008

The main mission of any long-running TV show should be to avoid repetition—we're looking at you, Dexter. Entourage's fifth season is all about shaking up the status quo and making the boys poor, and no episode is more dedicated to that storyline than "The All Out Fall Out," which finds the once mighty Vincent Chase relegated to appearing at a spoiled brat's sweet 16 to get out of the red, exposing cracks in his self-acclaimed dignity.


The episode still manages to stroke the quintessential guy fantasy with Ari in full alpha-male mode, complete with a brand new Ferrari, bitching out a nemesis agent in front of all his peers and coming home to a hot wife, all on his birthday.

3. "Busey And The Beach"

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Season: 1

Air Date: August 22, 2004

Entourage's defining episode is also the first season's strongest installment, clearly laying out the formula and tone for the show's future. Gary Busey provides a cameo that's more than just a quick "Hey it's that guy" role, incorporating him into the plot in a way the show would later feel comfortable doing with actual A-listers.


Our first real look into the wacky rapport between Ari and Mrs. Ari (Perrey Reeves), while also confirming that Ari as a character is indeed here to stay after he completely blacks on a rival agent trying to woo Vince. There's also a nice scene of the guys enjoying the California sunset at the end to drive home what the show's all about: best friends living the life, together.

2. "One Day In The Valley"

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Season: 3

Air Date: June 18, 2006 

The next best fantasy to the one this show is built around is randomly meeting and hanging out with "cool" celebs, such as Vincent Chase. That's what the gang does for two nerds they meet at an Aquaman screening, in an earnest and honest episode that finds Vince, allegedly not in it for the fame, sweating it out as the numbers for Aquaman's opening weekend surface.

1. "Vegas Baby, Vegas!"

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Season: 3

Air Date: August 6, 2006 

The final minutes of this episode are the funniest Entourage has ever delivered. It goes a little something like this: Vince and the gang co-opt Ari into a last minute trip to Vegas to blow off some steam. And from there everybody takes a backsteat to E and Drama as we're given dual storylines from both that unexpectedly converge with hilarious results.


Playing a fantastically douche-bag version of himself, Seth Green repeatedly pops up around town to taunt E about his and Sloan's history together, meanwhile the friendship between Drama and his male masseuse gets more and more suspect as the episode progresses. By episode's end, you'll never be able to hear the name Jackson Pollack again without smirking.

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