Entourage—The Boys Get Ready to Say Goodbye

The HBO series Entourage is such a hit, it’s hard to believe that in the early days the show had a hard time finding places to film and signing on guest stars. On July 20, the five main cast members—Kevin Connolly, Adrian Grenier, Kevin Dillon, Jerry Ferrara, and Jeremy Piven, along with Executive Producer Doug Ellin—appeared at the Paley Center for Media to look back on Entourage’s seven-year run and look forward to the final eighth season, with the first episode airing on Sunday, July 24.

Entourage began with the kernel of an idea: why not base a show on the popular Mark Wahlberg, chronicling his rise as a Hollywood star and his penchant to surround himself with his brothers and close friends. Wahlberg signed on as executive producer, but balked at the idea of doing a reality show, with cameras actually following him around. Thus was born the fictional Entourage.

Doug Ellin created the series and still writes most of the episodes, along with Ally Musika, who began as Ellin’s assistant. (Ellin joked that after Musika turned up her nose at one of his scripts, he challenged her to write something better. She did). Casting Entourage meant holding multiple auditions with numerous actors playing off against each other. One thing the final four had going for them? They are originally from the New York area—Grenier, Manhattan, Connolly, Staten Island, Ferrara, Brooklyn, and Dillon, Mamaroneck—perfect in the roles of four guys with East Coast attitude relocating to Los Angeles.

Entourage is the quintessential buddy show. Vincent Chase, played by Grenier, is Wahlberg’s doppelganger, a rising star who travels with his posse—brother Johnny “Drama” (Dillon), best friend and now manager, Eric or “E” (Connolly), and chauffeur and go-fer Turtle (Ferrara). The quartet lives together and plays together, freely indulging in alcohol, drugs, sex, and the luxury excess that seems to epitomize the celebrity lifestyle. (Connolly joked that fans are always disappointed to learn that the four stars are not actually roommates). Each season is a roller-coaster ride, with Vince’s fortunes, and thus the group’s, going up and down in true Hollywood style.

Media critic, Elvis Mitchell, who served as moderator for the Paley panel, asked each actor how closely he resembles his character. “Growing up in a theater family, I couldn’t be more fundamentally different from a Hollywood shark,” said Piven, who has won three Emmy Awards for playing the abrasive agent, Ari Gold.  “As actors, we deal with agents a lot,” Piven said, adding that he has been doing research “for a couple of decades.” In fact, the character of Ari Gold was based on real life agent, Ari Emanuel, brother of Rahm Emanuel, now Mayor of Chicago and once President Obama’s Chief of Staff.

Of the four actors, only Grenier admitted that he is somewhat like his fictional counterpart. “I have this natural nonchalance and I like people,” he said. “Vince’s quality is his selflessness. He could easily do without all the glitz and glamour.” Friendships are important to Vince. “He’s the glue that holds the group together.” Dillon said he was thankful he wasn’t like Johnny Drama, who “has issues and is explosive,” but he said the character is the best role he’s had.

Connolly said he doesn’t have much in common with “E,” but added that the actor who is least like his character is probably Ferrara, once described by Connolly as “domesticated.” On the show, Ferrara’s Turtle has undergone a metamorphosis. In one of the first episodes, Turtle is in a hot tub telling a young woman, “Come on let’s make out. I’ll show you where Vince eats breakfast.” By the seventh season, Turtle is dating Jamie Lynn-Sigler, who plays herself on the show, starting businesses, going to college, and becoming a celebrity in his own right.

While fans took to the show immediately, the actors were slower to develop the group’s camaraderie. “The first two episodes were well received, but in the early days, we were trying to figure it out, because we didn’t know what the relationships were,” said Ellin. Everything finally came together in the third episode when Vince and Johnny appear on The Jimmy Kimmel Show. “It just clicked,” said Grenier. “I felt like I knew the group my whole life.”

That episode was filmed on the Kimmel set. Finding locations was a challenge in the early days, with the actors literally crashing other events—the Red Carpet at the Cannes Film Festival, courtside at a Lakers Game, for example—so the crew could nail the right shots. Entourage set up eight cameras at a U2 concert and convinced Bono to wish Johnny Drama happy birthday during the performance. Ellin added, with a laugh: “That was a magical moment,” particularly because most people at the concert, unfamiliar with the show, were annoyed with Entourage’s entourage. “People kept asking, `who are these people and what are they doing?’” said Ellin.

Circumventing the lack of sets, Entourage employed the “five-page walk and talk” where the group strolls down an L.A. street while being filmed. Ellin said there’s pressure on the actors to get the scene right the first time because there are no cuts. (Pressure on the film crew, too, since they have to carry heavy cameras and walk backwards, sometimes up stairs). Those walk and talks have now become one of the show’s trademarks.

The obstacle for signing guest stars was cleared in season one’s fifth episode when Val Kilmer appeared as a sherpa who grows organic marijuana. Kilmer’s features were obscured beneath a scruffy gray beard, but there was no covering up the star power he brought to the show. “To get [stars to do] cameos, we were struggling,” admitted Dillon. After Kilmer, the stars just kept coming with many campaigning to be on the show. Celebrities who have appeared include: Gary Busey, Scarlett Johansson, Ralph Macchio, Jamie Pressly, Bob Saget, Brooke Shields, Edward Burns, Anna Faris, Larry David, Mary J. Bilge, Snoop Dogg, Kayne West, Tony Bennett, the women of The View, Peter Berg, Jamie Lynn Sigler, Matt Damon, and many others.

Besides stars, many famous directors have signed on to direct Vince’s fictitious films. Ellin brought laughter to the Paley audience when he observed that even when being linked to a made-up film, these ego-driven directors are particular about the projects they select. James Cameron agreed to direct Vince in Aquaman only after he was assured that the film would be a big hit. Martin Scorsese didn’t want to direct a biker film, but finally agreed to direct Vince in a remake of the Great Gatsby.

So what will happen in the final season? Ellin promised that some of the popular characters—Billy Walsh played by Rhys Coiro and Scott Lavin played by Scott Caan—will return with story arcs. Vince will worry about the gang breaking up, with E engaged, Johnny and Turtle busy with new projects. And relationships with coworkers and female love interests will continue to be volatile.

Seeing Entourage end is bitter sweet. “This show changed my life; it changed my whole family’s life,” said Ferrara. Piven said he is happy the show will be going out on top with the public still wanting more. (Ellin confirmed that there will be a film, something that will help “soften the blow.”)

“This show couldn’t have happened at a better time in my life,” said Dillon. “It’s been a great run, a great ride.” Added Grenier: “This season could be our best yet. I feel joyous.”

Go to the Paley Center for Media website for more information on upcoming programs.


About Charlene Giannetti (928 Articles)
Charlene Giannetti, editor of Woman Around Town, is the recipient of seven awards from the New York Press Club for articles that have appeared on the website. A graduate of Syracuse University’s S.I. Newhouse School of Public Communications, Charlene began her career working for a newspaper in Pennsylvania, then wrote for several publications in Washington covering environment and energy policy. In New York, she was an editor at Business Week magazine and her articles have appeared in many newspapers and magazines including the New York Times. She is the author of 13 non-fiction books, eight for parents of young adolescents written with Margaret Sagarese, including "The Roller-Coaster Years," "Cliques," and "Boy Crazy." She and Margaret have been keynote speakers at many events and have appeared on the Today Show, CBS Morning, FOX News, CNN, MSNBC, NPR, and many others. Her new book, "The Plantations of Virginia," written with Jai Williams, was published by Globe Pequot Press in February, 2017. Her podcast, WAT-CAST, interviewing men and women making news, is available on Soundcloud and on iTunes. She is one of the producers for the film "19 Daniel Highway," focusing on the opioid crisis that will be filmed in 2019. Charlene divides her time between homes in Manhattan and Alexandria, Virginia.