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1!!The Series
2* AlternativeCharacterInterpretation: [[http://www.cracked.com/video_19394_why-entourage-most-elaborate-prank-all-time.html This video]] posits that the show is an elaborate prank on the actors playing Vince and his crew, cruelly making them play successful actors when their real careers are depressing at best.
3* ArcFatigue:
4** Roughly half of the show follows the development of Vince's passion project, ''Medellin''. It's first introduced in early Season 2, before becoming the direct cause of most of the drama in Season 3 (which should be noted had an 8 month long gap in the middle and was twice as long as every other season of the show) and Season 4, whilst Season 5 is about rebuilding Vince's career after the film bombs.
5** The "Vince fires Ari" arc in Season 3, which takes most of the second half of the season to resolve. Making matters worse, is that Season 3 is the longest season of the show at twenty episodes; the arc starts in the first half of the season, [[ScheduleSlip has an 8 month break in the middle]], and then isn’t resolved until a few episodes before the season’s end - meaning the arc is actually longer than some seasons of the show.
6** Eric and Sloan's WillTheyOrWontThey, which rubs from late Season 2 all the way to the end of Season 8. And then happens ''again'' in the movie.
7** Vince's Season 6 "plot" of just standing around waiting for his next film to start shooting.
8* SugarWiki/AwesomeMusic: The series ends with Led Zeppelin's "Going to California," underscoring the bittersweet tone and foreshadowing Ari's final move after his call in TheStinger.
9* BaseBreakingCharacter:
10** Vincent Chase. While he still has some fans for him being a NiceGuy to his friends, he also has a lot of detractors who dislike him for being a VanillaProtagonist whose supposed "acting talents" come off as InformedAbility.
11** Eric 'E' Murphy. Some like his snarky know-it-all attitude and role as the OnlySaneMan to balance out the eccentric attitudes of the rest of the cast. Others dislike him for this same reason, finding him the least fun part of every episode. Not to mention his constant WillTheyOrWontThey subplot with Sloan, which occupies the entirety of the series since Season 2.
12* BestKnownForTheFanservice: The gratuitous amount of MaleGaze, with many cases of female nudity, is one of the best-remembered aspects of the show.
13* BrokenBase: The series has always received plenty of flack for its treatment of women, who usually are portrayed as some form of [[LustObject sex object]], and the number of times women speak to one another in the entire show is 8.5 times. To some, this makes the whole show some male fantasy trip, to others it... makes the show a male fantasy trip. It really depends on if you can hold on to the notion that the show is a parody of the shallow Hollywood lifestyle.
14* CatharsisFactor: During [[SeasonalRot Season 7]], when Music/{{Eminem}} punches out a [[TookALevelInJerkass coked out and belligerent Vince]] after the latter insulted him at his own party. Also doubles as a SugarWiki/MomentOfAwesome.
15* CrossesTheLineTwice: Practically ''everything'' that Ari Gold says. His insults come off as so blatantly offensive and tasteless that it comes off as funny in a morbid kind of way.
16-->'''Mrs. Gold:''' ''(reading off a tabloid)'' After a staff meeting, Ari threw a stapler at the wall and screamed at a fellow agent that he needed to climb back inside his mother's vagina and cook a little longer.\
17'''Ari:''' [[NotHelpingYourCase That's pretty funny]].
18* EnsembleDarkhorse:
19** Ari Gold quickly became one of the most popular characters in the show and gained more prominence during the second season. Many consider him to be the sweet saving grace of the show and why some fans continue watching it in the first place.
20** Eccentric and temperamental director Billy Walsh was also quite popular with fans of the show.
21* FanPreferredCouple: Many fans wanted Ari to stay with Dana Gordon and not go back to his estranged wife.
22* FridgeBrilliance: Many people have noted that despite Vince being the "alpha" of the group, he's the least interesting of the main characters. But then you realize that the show is called ''Entourage'' for a reason; it's more about Vince's friends than Vince himself. This is hammered in during the sixth season, when Vince spends the season just waiting for his next project to start.
23* HarsherInHindsight:
24** Vince literally gaslights Music/MandyMoore and tries to get her fired because he feels slighted by her romantically. This becomes uncomfortable given the circumstances of the deterioration of Mandy's own marriage in real life.
25** Ari's constant misogynistic verbal abuse towards his female employees comes off like this in light when Creator/JeremyPiven was later accused of a number of sexual misconduct situations (several of which allegedly took place during the time he was starring in the show), which just adds to the general unease of certain elements which have aged badly.
26** After Ari's abusive nature is exposed in Season 7, Creator/JeffreyTambor swings by to offer support, stating that he's "no stranger to scandal". Ari comically asks, "Oh really? What scandal?", leading Tambor to reply, "There was an incident on ''Series/ArrestedDevelopment''. No reason you would have ever heard of it". The gag is supposed to be that Tambor is a boring goody two-shoes who would never be near scandal. Many years later, Tambor's career would be affected by accusations of sexual misconduct, and he would be infamously accused of repeatedly screaming at his ''Arrested Development'' co-star Creator/JessicaWalter (with the abuse so bad that Walter broke down into tears just remembering it, and the ''Arrested Development'' cast going into civil war). Suddenly, the show feels like it was grimly predicting Tambor's downfall for comedy.
27** Doug Ellin admitted in a 2021 interview that he retroactively regretted the Harvey Weinstein parody character from the series. The regret was that the worst Ellin knew about Weinstein was the bullying and the occasional empty death threat. Ellin admitted he had no clue about the sheer criminal sexual depths of the real Weinstein, and if he had, he would never done even a parody of Weinstein.
28* HilariousInHindsight:
29** The show's RealSongThemeTune is "Superhero" by Music/JanesAddiction. Vince takes the lead role in a superhero movie, specifically Creator/JamesCameron's ''ComicBook/{{Aquaman}}''.
30** In the second episode, Creator/JessicaAlba says "fantastic". She later acted as the Invisible Woman in ''Film/FantasticFour2005'' and ''Film/FantasticFourRiseOfTheSilverSurfer''.
31** In Season 2 (Airing in 2005) Vince is originally opposed to the idea of playing a superhero, worried that he'd just wind up in a campy film like ''Film/BatmanForever'' or ''Film/BatmanAndRobin''. A few years later, roles in superhero films started to become much more sought after.
32** Ari's remark about NBC when Drama's worried they might cancel his new show, ''Five Towns''.
33--->'''Ari:''' They gave ''Series/{{Joey}}'' two seasons, NBC don't cancel shit.
34** Ari ridicules Creator/PeterDinklage repeatedly (even mocking his height directly to his face). While notable as an actor in 2005, Dinklage would become universally loved the world over (and rake in countless awards and become extremely wealthy) when he got to star in ''Series/GameOfThrones'' just a handful of years later. Ari probably wishes he'd been nicer to what could have a hugely profitable client.
35** In the first season finale, Johnny flips out when he spots a crewmember sending a text message during an audition, leading to him pulling a ScrewThisImOuttaHere. Four years later, Creator/ChristianBale got similarly worked up about someone doing stuff in his eyeline while filming ''Film/TerminatorSalvation''.
36** Years after the show joked about an ''ComicBook/{{Aquaman}}'' movie directed by Creator/JamesCameron, an actual ''Aquaman'' movie directed by Creator/JamesWan began development for the Franchise/DCExtendedUniverse. Even funnier is that ''Film/Aquaman2018'' was in part with the technology that James Cameron developed for the ''Film/{{Avatar}}'' sequels, which was made to film underwater.
37*** This also means that in the ''Entourage'' universe, the DC movie universe ''Aquaman'' would be another film franchise getting a reboot in the 2010s. And when one considers ''Aquaman'''s use as an Expy for the ''ComicBook/SpiderMan'' film that James Cameron almost directed, it's rather fitting considering that the Spider-Man films have been [[Film/TheAmazingSpiderMan rebooted]] [[Franchise/MarvelCinematicUniverse twice]].
38*** Funnier still, ''Film/{{Aquaman|2018}}'', as of January 2019 broke all box office records for a DC-based superhero (even ''Film/TheDarkKnight'') movie, meaning the show was more prescient than mocking.
39** Creator/PattyJenkins directs a couple of episodes, one of which features a storyline of Creator/WarnerBros being completely overwhelmed with happiness due to the success of a fictional DC movie. Jenkins herself would no doubt experience the same gratitude from executives after ''Film/{{Wonder Woman|2017}}'' was a huge success for the studio.
40** In season 6, [[Series/TheFlash2014 Iris West is Reverse Flash's assistant]]. Which gets even funnier when one realizes that [[spoiler:it isn't really that far removed from what Reverse Flash actually ''does'' in the show's first season]].
41** Season 4 follows Vincent's attempts to develop his passion project, "Medellin", a biopic of infamous drug lord Pablo Escobar. Strenuous production difficulties for Vince's movie result in a disastrous Cannes premiere, panning by critics, and a direct-to-video release in the United States. In real life, Creator/KevinConnolly would direct and Rhys Coiro would star in Creator/JohnTravolta's passion project, ''Film/{{Gotti}}'', a biopic of infamous mafia don John Gotti. Strenuous production difficulties for the real movie would ultimately result in [[LifeImitatesArt a disastrous Cannes premiere, panning by critics, and a direct-to-video release in the United States.]]
42** Creator/{{Aaron Sorkin}} makes a memorable cameo in Season Six where, in a desperate effort to sign him, it's suggested that Sorkin move into directing. Sorkin immediately brushes this off, flatly stating "I don't wanna direct. I'm a writer. I like writing. I could have directed years ago if I wanted to". Nearly a decade after this episode aired, Sorkin would indeed move into directing with Film/{{Mollys Game}}. Additonally, Sorkin appeared to enjoy directing a movie so much that he's transitioned into that frontier. So maybe Entourage convinced him? (But probably not)
43** Season 4 has Ari pitch "Silo", a film about a secret underground society living under a farm silo. In 2023, [=AppleTV+=] release ''Series/{{Silo}}'', a series about a secret underground society.
44* JerkassWoobie: Ari becomes one in "The Beginning Of The End" - [[spoiler:When Mrs. Ari tells him that she's started seeing someone else, he looks utterly crushed]].
45* RetroactiveRecognition: In the Season 6 episode "Amongst Friends" (2009), the gang is attending the premiere of Creator/MartinScorsese's new film, ''Gatsby''. Eric and Sloan decide to go there as just friends, while Johnny turns up with his date for the day. The buddies rent a limousine for the occasion and Vince is accompanied by a very beautiful model named Lisa, who's played by Creator/GalGadot, a few years before she became a bona fide star by playing the Franchise/DCExtendedUniverse's Wonder Woman.
46* TheScrappy:
47** The character of Dom, whom most fans found to be obnoxious and unfunny. He was intended to become a permanent member of the cast but was quickly written out of the show because the fans hated him. He's also this in-universe in his debut episode, humorously, with Eric, Turtle, and Drama unable to stand his presence.
48** Ashley, Eric's crazy stalker girlfriend from Season 6 is widely disliked by fans of the show.
49** In season 7, Vince begins dating real-life porn star Sasha Grey. Many fans loathed her character as well as the entire story arc of Vince's descent into a world of HookersAndBlow.
50* SeasonalRot:
51** It's debatable, but complaints about the show going downhill surfaced somewhere around season 3.
52** Many fans have agreed that season 7 is the show's lowest point, criticizing it for losing much of its warmth and humor and becoming a DarkerAndEdgier drama. As a result of the fans' complaints, Season 8 returned to a tone more in line with the earlier seasons, with a greater focus on humor and heartwarming moments.
53* StrawmanHasAPoint: Verner Vollstedt may have been trying to get Vince to quit ''Smokejumpers'', but he makes legitimate points about Vince's acting and forces him to step up his game.
54* StrangledByTheRedString: Vince getting ''married'' in the finale, one episode after getting the girl to agree to go on a date with him. There was no TimeSkip. And then TheMovie reveals the marriage ended soon after anyway.
55* UnintentionalPeriodPiece: The episode "I Love You Too" shows just how different Hollywood and pop culture were in the 2000s. Vince and the gang attend the San Diego Comic Con so Vince can promote ''Aquaman'' and Drama can do a panel for ''Viking Quest''. The episode clearly takes place during a time when comic books and sci-fi were still seen as niche genres by Hollywood and Vince's crew was reluctant to go because the event was strictly for geeks. Nowadays, the genres are the biggest money makers and Comic Con, which has expanded to includes all kinds of pop culture, is one of the film industry's biggest yearly events.
56* UnintentionallyUnsympathetic: While Ari Gold's {{Jerkass}} nature makes him an UnsympatheticComedyProtagonist, his main redeeming quality of his extreme devotion to his wife ironically makes him fall under this trope. This devotion ends up coming off as clingy possessiveness, with Ari often treating her with contempt and boasting behind her back about various affairs (that admittedly probably never happened). Despite her wishes for therapy, he treats their sessions as a cruel punishment and frequently blows them off. He never refers to her by name, often mockingly calling her "Mrs Ari Gold". He reacts with undue rage and disgust when she has the gall to restart her abandoned acting career in a soap opera and makes out with a male costar in a scripted scene. Mrs Gold is seldom portrayed sympathetically, more often than not, she's shown to be nagging and hindering Ari when he has some vital storyline that needs dealing with. Ari is so completely obsessed with his wife that he develops a season long breakdown when she leaves him, and while the show treats him as the hero trying to win her back, given his literal years of neglect, it has some fairly ugly implications as to how toxic his love for her really is.
57* VanillaProtagonist: It's called "Entourage" for a reason.
58* TheWoobie:
59** You can't help but want to give Lloyd a hug every now and then, considering how much he's suffered as Ari's assistant, who constantly insults him with racist and homophobic remarks. Fortunately, Season 6 has Ari [[ThrowTheDogABone throw him a bone]] by making him an agent like he wanted.
60** Dana Gordon in Season 8. [[spoiler:She and Ari rekindle their old romance after Ari and his wife separate. Dana falls back in love with Ari and wants to have a child with him even though she's nearly 40 years old. But in the end Ari realizes that he's still in love with his wife and breaks off his relationship with Dana, leaving her heartbroken.]]
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62!!The Film
63* HarsherInHindsight: Vince dates a former girlfriend of Creator/ArmieHammer, prompting Hammer to briefly confront Vince and threaten to "sneak up behind and snatch the life" out of him if Vince doesn't stay away. Many years later, Hammer would be rocked by numerous accusations of being violently possessive of various girlfriends, to the point of carving his own initials into them. Retroactively, Hammer threatening to kill Vince for even being with a former girlfriend, as well as the clear sense of ownership he feels over a woman even after they stop dating, now feels deeply disturbing.
64* ItsTheSameNowItSucks: The biggest complaint about the film was that it was essentially a 105 minute long episode of the show with the characters going through their usual plot lines.
65* TheyWastedAPerfectlyGoodPlot: The series ended with a stinger showing that Ari was being tapped to lead Time Warner, as John Ellis is planning to retire and offers him the job. The opportunities for a man like Ari in charge of one of the world's biggest production studios were endless, but come the time of the movie (which starts immediately after this), Ari is seemingly right back in his old Hollywood agent role and barely gets any time in the new job when [[spoiler:he's forced out by the backer of the film ''Hyde'']]. With the underperformance of the film, any such possibilities of Ari taking on a new job are likely never going to happen.

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