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* 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/{{Spider-Man}}''... Only for ''PiratesOfTheCaribbean: Dead Man's Chest'' to open a week after that episode aired & 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.]]
* DesignatedProtagonistSyndrome: You'll be hard pressed to find anybody that actually watches the show for Vincent Chase and not the supporting cast.
** [[FridgeBrilliance Well, it is called Entourage...]]
* 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.
* HeyItsThatGuy: Creator/KimCoates plays douchebag producer Carl Ertz in two episodes. Crosses over with RetroactiveRecognition as Kim was just gaining mainstream profile from Series/SonsOfAnarchy at the time.
* 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.
* 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.
* SeasonalRot: Its debatable but complaints about the show going downhill surfaced somewhere around season 3.
* 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. And to clarify, there was no TimeSkip.
* UnfortunateImplications. Particularly in the early seasons it's really hard not to be put off by the rampant misogyny. Women are very openly treated as sex objects and, other than Shauna, there aren't really any female characters that act as anything other than skirts for the guys to chase. The show itself doesn't actually comment on the morality at play, leaving it somewhat open to interpretation, and a [[TruthInTelevision show focused heavily on male-friendship and masculine banter]] will always have to deal with this. Later seasons improve though, with more female characters in non-relationship roles and an increased focus on the growing maturity of the characters.
* 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.]]

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