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The Best Seasons of 'Entourage'

Updated May 15, 2020 975 votes 370 voters 47.7k views8 items

List RulesVote up the best seasons of Entourage.

All the seasons of Entourage have been great, but which seasons really stand out? Vince Chase navigates the ins-and-outs of Hollywood thanks to a little help from his friends. Some of the most memorable episodes of Entourage come from different seasons, so picking the top season isn't easy. To determine once and for all what the best seasons of Entourage are, let's rank every Entourage season from best to worst. And if you've finished the show and are looking for something new instead, try taking a look at our list of shows like Entourage for suggestions!

Entourage is an American comedy-drama series – created by Doug Ellin – that follows Vince and his entourage as they develop their careers and look for love in La La Land. Entourage premiered on HBO on July 18, 2004, and aired eight seasons before concluding on September 11, 2011. The talented cast included Adrian Grenier, Kevin Connolly, Kevin Dillon, Jerry Ferrara, and Jermey Pivan.

Vote up your favorite seasons of Entourage, and vote down any bad seasons that you really didn't enjoy, despite how much you loved any individual episodes. It can be painful to put one Entourage season over the other when there are so many good ones, which is why you can vote on however many seasons you like.

  • Photo: HBO

    Entourage - Season 2

    The second season of Entourage premiered on June 5, 2005, and contains 14 episodes. This season primarily centers around Vince's role as Aquaman in an upcoming film.

    This season has several unforgettable episodes including: "The Boys Are Back in Town," "I Love You Too," and "Exodus."

    Memorable moments from Season 2 include:

    • Vince hooks up with Mandy Moore.
    • Ari gets fired from his agency.
    • Vince and Drama go to Comic-Con.
    Is this one of the best?
  • Photo: HBO

    Entourage - Season 3

    The third season of Entourage premiered on June 11, 2006, and contains 20 episodes which aired in two parts. This season focuses on Vince's post-Aquaman options and Drama's new success.

    This season contains several unforgettable episodes including: "Three's Company," "Vegas Baby, Vegas!," and "Gotcha."

    Memorable moments from this season include:

    • Eric and Sloan have a threesome.
    • Vince fires Ari.
    • Drama's show "Five Towns" becomes a hit.
    Is this one of the best?
  • Photo: HBO

    Entourage - Season 1

    The first season of Entourage premiered on July 18, 2004, and contains eight episodes. This season follows Vincent Chase and his group of friends as his acting career begins to pick up steam.

    This season has many unforgettable episodes including: "Entourage," "The Script and the Sherpa" and "New York."

    Memorable moments from Season 1 include:

    • Vince signs on to do "Queens Boulevard" with Billy Walsh.
    • Vince appears on Jimmy Kimmel's show.
    • E officially becomes Vince's manager.
    Is this one of the best?
  • Photo: HBO

    Entourage - Season 5

    The fifth season of Entourage premiered on September 7, 2008, and contains 12 episodes. This season focuses on the ups and downs of Vince's career.

    This season contains several unforgettable episodes including: "Unlike a Virgin," "Tree Trippers," and "Return to Queens Blvd."

    Memorable moments from Season 5 include:

    • Vince and the guys take mushrooms at Joshua Tree.
    • Turtle meets Jamie-Lynn Sigler.
    • Drama has a melt-down on The View.
    • Vince gets rejected by Gus Van Sant and hired by Martin Scorsese.
    Is this one of the best?