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1Vincent Chase / Adrian Grenier

Grenier, pictured here at the Season Two premiere in Hollywood in 2005, had been in a handful of movies when he won the role of Chase.
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Although Entourage was Grenier's most notable role to date, he continues to act as well as serve as a campus advisor for the Academy of Global Citizenship. Here Grenier, now 44, is pictured at the Australian Open in 2020. His most recent project is a series for Netflix titled Clickbait.
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3Jeremy Piven / Ari Gold
Jeff Kravitz//Getty ImagesJeremy Piven had been acting since the '80s when he started playing Ari Gold, Vincent Chase's high-powered and overly caffeinated agent. He won an Emmy three times for his role. Here he's pictured with his first statue in 2006.
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4ZAK BENNETT//Getty ImagesNow 52, Piven—pictured at the Grand Opening of the Guitar Hotel expansion at Seminole Hard Rock Hotel & Casino Hollywood in Hollywood in 2019—most recently appeared in the CBS show Wisdom of the Crowd, which was canceled after two seasons, and started a podcast. Since 2017, a number of women have accused him of sexual misconduct, which he has categorically denied.
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5Kevin Connolly / Eric "E" Murphy
Evan Agostini//Getty ImagesKevin Connolly, who plays Vincent Chase's best friend and eventual manager Eric "E" Murphy, had acted since the early '90s when he got the role in Entourage. Here he's pictured at the Season Two premiere in New York City in 2005.
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6Paul Archuleta//Getty ImagesConnolly, now 47, has continued to act and has become a director. He helmed 2018 biopic Gotti starring John Travolta. He's pictured here in 2019 at a charity holiday party in Los Angeles.
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7Kevin Dillon / Johnny "Drama" Chase
Patrick McMullan//Getty ImagesKevin Dillon, pictured here at the Season Two premiere in New York City in 2005, played Vincent Chase's older half-brother Johnny "Drama" Chase. Dillon, who is Matt Dillon's brother in real life, appeared in numerous movies before Entourage, including Oliver Stone's The Doors. He earned three Emmy nominations for his portrayal of Johnny Drama in Entourage.
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8Robin L Marshall//Getty ImagesNow 55, Dillon, pictured at a charity gala in Malibu in 2018, continues to act, having recently appeared in the cop drama Blue Bloods. Jerry Ferrara, who played Turtle on Entourage was the best man at his wedding in 2006; Kevin Connolly walked his wife down the aisle.
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9Jerry Ferrara / Turtle
Evan Agostini//Getty ImagesJerry Ferrara, pictured at the New York City premiere of Season 2 in 2005, had a handful of small TV roles before playing Vincent Chase's friend Turtle.
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10Slaven Vlasic//Getty ImagesFerrara, now 41, continues to appear in movies and TV, including the Starz's show Power. He's pictured here in 2019 promoting the Starz show.
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11Perrey Reeves / Melissa Gold
Jason Kempin//Getty ImagesPerrey Reeves played Ari Gold's wife, Melissa Gold. She had acted in movies and TV since the late '80s. Here she's pictured at the Season 5 premiere in New York City.
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12Albert L. Ortega//Getty ImagesReeves, pictured here in 2019 at HBO's Official Golden Globe After Party in L.A., continues to act, having appeared in a number of television shows, including Freeform's Famous in Love.
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13Rex Lee / Lloyd
Alberto E. Rodriguez//Getty ImagesRex Lee, who played Ari Gold's long-suffering assistant, Lloyd Lee, had several behind-the-camera jobs before Entourage, as well as acted in a children's theater company. Here's he's pictured at the Season Three premiere in 2007 in L.A.
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14Rebecca Sapp//Getty ImagesLee, pictured here at the pre-Oscar style lounge in 2017, is now 52. From 2014 to 2018, he played the lead role in the TV Young & Hungry.
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15Debi Mazar/Shauna Roberts
Alberto E. Rodriguez//Getty ImagesActress Debi Mazar arrives at the premiere of the HBO original series "ENTOURAGE" on April 05, 2007 in Los Angeles, California.
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16Jose Perez/Bauer-Griffin//Getty ImagesDebi Mazar is seen at the film set of the 'Younger' TV Series on February 11, 2021 in New York City.
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17Constance Zimmer/Dana Gordon
Alberto E. Rodriguez//Getty ImagesActress Constance Zimmer arrives at the premiere of the HBO original series "ENTOURAGE" on April 05, 2007 in Los Angeles, California.
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18JEAN-BAPTISTE LACROIX//Getty ImagesUS actress Constance Zimmer poses in the press room during the 72nd Annual Directors Guild of America Awards at the Ritz Carlton Hotel in Los Angeles on January 25, 2020.
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19Rhys Coiro/Billy Walsh
Stephen Shugerman//Getty ImagesActors Rhys Coiro and Katherine Cunningham-Eves attend the premiere of HBO's "Entourage" at the Cinerama Dome on June 1, 2006 in Hollywood, California.
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20Randy Shropshire//Getty ImagesActor Rhys Coiro at the Easterseals Disability Film Challenge Awards Ceremony on May 9, 2019 at Sony Pictures Entertainment, honoring films that promote inclusion and diversity in the entertainment industry.
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