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!! The Series
* ArcFatigue:
** 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 is long enough that it could have been two seasons) & Season 4, whilst Season 5 is about rebuilding Vince's career after the film bombs.
** The "Vince fires Ari" arc in Season 3 - it takes most of the second half of the season to resolve.
** Eric & 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.
** Vince's Season 6 "plot" of just standing around waiting for his next film to start shooting.
* BrokenBase: The series has received plenty of flack for it's treatment of women, usually 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 shallow parody of the Hollywood life style.
* CrazyAwesome: Ari Gold and Billy Walsh.
* CrowningMomentOfFunny:
** Who knew [[Creator/MattDamon Matt]] [[http://www.youtube.com/watch?v=MxODvIILFq8 Damon]] could be this funny?
** A meta-instance -- Vince's ''ComicBook/{{Aquaman}}'' gets the highest grossing box office opening in history, beating ''Film/SpiderMan1''... Only for ''Film/PiratesOfTheCaribbeanDeadMansChest'' to open a week after that episode aired and do that same feat in RealLife, and beating out the fictional gross for ''Aquaman'' to boot.
* CrowningMomentOfHeartwarming: Ari and the headmaster share a moment in Season 4 when Ari goes over to the headmaster's house to try to convince the headmaster to let his son into the same private school as his sister, Ari [[spoiler:tearfully acknowledges what he did to make the board not want to let his son in, the headmaster then confesses to Ari that he has a 'special' son who works in the mail room at another agency, he then tells Ari that if he gives him a better job at his agency he'll let Ari's son into the school.]]
* EnsembleDarkhorse: Ari quickly became one of the most popular characters in the show, and gained more prominence in the show during the second season.
** Eccentric and temperamental director Billy Walsh was also quite popular with fans of the show.
* EpicFail: ''Medellin'' almost killed Vince's career, and looks like it may have killed Billy Walsh's.
* FoeYay (Ari's admonitions of Lloyd usually involve something sexual)
--> '''Ari:''' That was a great speech, Lloyd. Yeah, if I was 25 and liked cock, we could be something.
** Ari's admonitions of pretty much ''everyone'' involve something sexual.
* HilariousInHindsight:
** Ari's remark about NBC when Drama's worried they might cancel his new show, ''Five Towns''.
--> '''Ari''': They gave ''Series/{{Joey}}'' two seasons, NBC don't cancel shit.
** 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''.
** Years after the show joked about an ''ComicBook/{{Aquaman}}'' movie directed by James Cameron, an actual ''Aquaman'' movie directed by James Wan began development for the Franchise/DCCinematicUniverse.
*** This also means that in the Entourage universe, the DCCU ''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]].
* 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]].
* TheScrappy:
** 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.
** Ashley, Eric's crazy stalker girlfriend from Season 6 is widely disliked by fans of the show.
** 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.
* SeasonalRot:
** Its debatable but complaints about the show going downhill surfaced somewhere around season 3.
** Many fans have agreed that season 7 is the show's low 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.
* StrawmanHasAPoint: Verner Vollstedt may have been trying to get Vince to quit ''Smokejumpers'', but he makes legitimate points about Vince's acting & forces him to step up his game.
* 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.
* VanillaProtagonist: It's called "Entourage" for a reason.
* TheWoobie: Dana Gordon in Season 8. [[spoiler:She and Ari rekindle their old romance after Ari and his wife seperate. 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.]]

!!The Film
* CriticalDissonance: The film received mostly negative reviews from critics, but fans of the show and casual moviegoers loved it. Case in point, the critics on Rotten Tomatoes gave the movie a 32% approval rating, while audiences gave it an 84%.
* 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.
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