- Crazy Awesome: Ari Gold and Billy Walsh.
- Crowning Moment of Funny:
- Who knew Matt Damon could be this funny?
- A meta-instance — Vince's Aquaman gets the highest grossing box office opening in history, beating Spider-Man... Only for Pirates of the Caribbean: Dead Man's Chest to open a week after that episode aired and 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.
- 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.
- Eccentric and temperamental director Billy Walsh was also quite popular with fans of the show.
- 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: They gave Joey two seasons, NBC don't cancel shit.
- Ari's remark about NBC when Drama's worried they might cancel his new show, Five Towns.
- 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 Screw This, I'm Outta Here!. Four years later, Christian Bale got similarly worked up about someone doing stuff in his eyeline while filming Terminator Salvation.
- 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.
- 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 Hookers and Blow.
- Seasonal Rot:
- 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 Darker and Edgier 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.
- Strawman 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. To clarify, there was no Time Skip. And then The Movie reveals the marriage ended soon after anyway.
- Vanilla Protagonist: It's called "Entourage" for a reason.
- The Woobie: Dana Gordon in Season 8. 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.