Entourage/YMMV

Crazy Awesome: Ari Gold.
Crowning Moment of Funny: Who knew Matt Damon can be this funny?
- A meta-instance - Vince's Aquaman gets the highest grossing box office opening in history, beatingSpider-Man... Only for Pirates of the Caribbean: Dead Man's Chest to open a week after that episode aired & do that same feat in Real Life, and beating out the fictional gross for Aquaman to boot.
Crowning Moment of Heartwarming: 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 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.
Designated Protagonist Syndrome: You'll be hard pressed to find anybody that actually watches the show for Vincent Chase and not the supporting cast.
- well it is called Entourage...
Ensemble Darkhorse: Ari quickly became one of the most popular characters in the show, and gained more prominence in the show during the second season.
Epic Fail: Medellin almost killed Vince's career, and looks like it may have killed Billy Walsh's.
Foe Yay (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.
Hilarious in Hindsight: Ari's remark about NBC when Drama's worried they might cancel his new show, Five Towns.

Ari: They gave Joey two seasons, NBC don't cancel shit.

Jerkass Woobie: Ari becomes one in "The Beginning Of The End" - When Mrs. Ari tells him that she's started seeing someone else, he looks utterly crushed.
The Scrappy: 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.
Seasonal Rot: Its debatable but complaints about the show going downhill surfaced somewhere around season 3.
Straw Man Has a Point: 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.
Strangled by the Red String: Vince getting married in the finale one episode after getting the girl to agree to go on a date with him.
Unfortunate Implications. 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 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.
Wham! Episode "Lose Yourself". Vince gets punched out by Eminem and busted for coke, Terrance McQuiewick wants E to sign a pre-nup, Turtle's future with Avion is uncertain, and Mrs. Ari leaves her husband. Wow.