The 10 Worst Career Decisions of Entourage's Vinnie Chase

by | June 1, 2015 | Comments

On Entourage, everything worked out for Vincent Chase (Adrian Grenier), even when it probably shouldn’t have. The show was about the camaraderie between Vince and his three childhood friends: E (Kevin Connolly), Turtle (Jerry Ferrara) and Johnny Drama (Kevin Dillon), even his agent Ari (Jeremy Piven). No matter what happened, they were in it together, but when you look back at some of the choices Vince made, it’s a little surprising he lasted eight seasons, only to have a movie about him hit theaters June 3.

In the Entourage movie, Vince decides to direct a movie version of Dr. Jekyll and Mr. Hyde. Could this finally be move that sinks Vinnie Chase? We doubt it, but it’s the perfect time to look back at some of the worst decisions Vince made in the eight years Entourage was on HBO.

10. Trying to Get Sasha Grey Out of Adult Movies

Not so much for the ethical dilemma of shoehorning his girlfriend into a movie for ulterior motives, but it was so condescending. When Vince started dating Sasha Grey (playing herself), he wanted her to stop doing adult films. He went so far as to try to get her a role in his movie Air-Walker. That would be a bad move in any relationship. Nobody wants to get the pity part, and nobody wants to be forced to cast your girlfriend. The real problem though was that Vince didn?t respect who Sasha was, so their relationship was doomed.

9. Giving Billy Walsh Final Cut

Medellin could have been Vincent Chase’s Oscar moment for playing Pablo Escobar, but the boys put too much faith in Billy Walsh (Rhys Coiro), since he had done right by them with Queens Boulevard. Walsh went a little Apocalypse Now down in Colombia, then wouldn’t even show them the first cut of the film. Under Walsh, Medellin was an epic failure and went straight to video. In real life, that would land Vince in Steven Seagal territory, but this was Entourage so it only lasted a season.

8. Showing Medellin at Cannes

Another Billy Walsh move, but this was such a massive miscalculation it deserves its own entry. Billy submitted to Cannes without E’s permission, or agreement. Billy expected a triumph, but Cannes was the nail in the coffin. It got booed off the screen and even put Ari to sleep. The only deal they could get was to sell it to a disgruntled producer for $1. Even Grace of Monaco got to premiere on Lifetime after its Cannes disaster!

7. Trusting Billy Walsh with Lost in the Clouds

How many of these have to do with Billy Walsh? During the whole Medellin fiasco, Walsh got hired to make the mountain-climbing movie, but he rewrote the script into the sci-fi movie Silo. Despite all that, Silo was considered good enough to make. But when Medellin bombed, the whole thing was off. See, it all goes back to Billy Walsh. Hollywood is about who you know, and if you know the wrong people they can sabotage your career.

6. Dating Mandy Moore

According to Entourage mythology, Vincent Chase had a small part in Mandy Moore‘s movie A Walk to Remember. For an extra to date the star of the movie, and a pop star at that, seemed like a young boy’s dream. But years later, it almost cost him Aquaman. Moore, playing herself, returned to Vince’s life as his Aquaman leading lady, and losing her again almost made him quit the film. Luckily, James Cameron saved the day (as he always does) and convinced Vince to do the movie, but imagine how awkward those underwater love scenes must have been.

5. Doing His Own Stunts

This is a serious one, because it led to drug addiction, which is no laughing matter, even in a comedy. What is funny is that Nick Cassavetes got cast as the balls-to-the-walls director pushing Vince to do his own stunts. Since when does Nick Cassavetes have a hardcore reputation? He directed The Notebook!

4. Dropping Out of Aquaman 2

Vince and E thought they were standing up for artistic integrity. James Cameron wasn’t directing the sequel. Andrew Kevin Walker wasn’t writing the script. In the world of Entourage, Michael Bay directing a Kevin Smith script may have been the ultimate insult. Still, there’s no nobility in breaching your contract. Sometimes honoring your commitments is more important than the end result. We never got to see what the Jake Gyllenhaal headlined Aquaman 2 looked like, but however bad it was, Vince could’ve made it better by being a team player and trying to protect the character from the inside.

3. Passing on Matterhorn

Matterhorn just sounds like the greatest idea for a movie ever, so it would have been worth it just to see a few fake scenes from it on an episode or two. It was “Die Hard at Disneyland” but Vince wanted to do something meaningful. Sure, his acclaimed turn in Queens Boulevard came out of it, but the world needed Matterhorn too.

2. Firing Ari

We get it. There was a hiatus coming and they needed a dramatic cliffhanger to leave us hanging. But Vince and E firing Ari was just an example of being a couple of little punks. There had been some friction, Ari disobeying their wishes with the Ramones biopic (see below), but Ari had been right. They would’ve had the Ramones if they’d followed Ari’s lead. It all came down to a miscommunication. Ari kept trying to wheel and deal to make Vince happy, when all Vince wanted was an apology. But Ari did apologize. It was just too late so they fired him. Way to be dramatic, Mr. Actor. But Ari was still the only person truly fighting for Vince, and they would learn that eventually.

1. Trusting Bob

In what may have been Entourage‘s most poignant story, Vince and E tried to do the right thing — but it was the wrong decision. Vince wanted to star in a Ramones biopic owned by producer Bob Ryan (Martin Landau). Out of loyalty, E insisted they keep Bob involved in the negotiations for the film against Ari’s advice. Bob was terrible in meetings. And even though we’re all still quoting him (“Would that be something you’d be interested in?”), the fact is no studio wanted to work with him. Involving Bob ultimately cost Vince the movie. Ari may have been a little mean, sending Bob to the wrong studio for a meeting, but it was a lose-lose situation. Bob’s retaliation to Ari was to sell the script to Warner Bros., then an enemy of Vince and Ari’s. No matter what, there was no way Vince was playing Joey Ramone with Bob involved. The right call would have been a nice credit and producer’s fee for Bob, but let the professionals make the movie.

Fred Topel is an entertainment journalist and film critic based in Los Angeles. Follow him on Twitter at @FredTopel and read his reviews here.

Tag Cloud

Marvel Studios ABC Best and Worst See It Skip It Interview hispanic Sundance Musical jamie lee curtis Paramount Network A&E X-Men Trophy Talk 2015 Comedy Netflix Christmas movies Holiday Nat Geo Mary Tyler Moore Set visit National Geographic foreign RT21 Red Carpet ESPN Fall TV First Look game of thrones Lionsgate Watching Series Amazon Prime Video cats zombies docudrama Stephen King spy thriller period drama cancelled TV series dramedy E! TCA 2017 christmas movies adventure true crime transformers A24 Superheroes Sneak Peek children's TV Rocky Adult Swim Universal TLC Trivia doctor who TBS Bravo Brie Larson Box Office Teen Comic Book comic dceu Extras Schedule justice league Trailer PBS Spring TV Walt Disney Pictures Marvel Television Epix BBC America Video Games AMC cartoon Toys Amazon Holidays mockumentary Heroines IFC 71st Emmy Awards political drama Warner Bros. award winner Crackle Cosplay Drama nature discovery Fox News YouTube Polls and Games LGBT Hulu Martial Arts slashers CW Seed 24 frames Netflix Election Chernobyl Opinion singing competition thriller San Diego Comic-Con Freeform Pet Sematary Britbox Pirates Cannes Paramount CBS All Access Film Creative Arts Emmys 2016 cancelled CMT Awards Avengers Marvel Action Emmys Western Premiere Dates police drama psycho Reality Competition Ovation NBC IFC Films History Winter TV psychological thriller DirecTV spain strong female leads 2017 science fiction DC Universe Tomatazos joker spider-man teaser comiccon Musicals stand-up comedy name the review mutant Hallmark USA Network TIFF game show Esquire canceled Unbreakable Kimmy Schmidt Dark Horse Comics Year in Review Summer Oscars American Society of Cinematographers TV Land CBS Columbia Pictures President Crunchyroll Chilling Adventures of Sabrina dc Disney+ Disney Plus Black Mirror Star Wars vampires Disney Channel MTV Logo cancelled TV shows robots Acorn TV Shondaland WarnerMedia Starz Hallmark Christmas movies animated independent versus rotten movies we love Captain marvel natural history Mary Poppins Returns zombie Song of Ice and Fire 2020 Disney ratings medical drama cooking talk show Showtime Amazon Prime unscripted Family crossover Cartoon Network blaxploitation DGA YouTube Red crime thriller facebook Binge Guide serial killer Comedy Central Kids & Family Pixar casting The Purge Rocketman boxoffice Spike Valentine's Day Horror free movies Elton John ghosts Mary poppins crime Super Bowl 007 spinoff Podcast technology ITV Awards Tour Nominations Spectrum Originals Christmas Grammys FXX RT History indie The Arrangement screenings 45 batman Certified Fresh The Walking Dead Film Festival The CW MSNBC Ghostbusters aliens Quiz Apple TV Plus television SXSW Disney Plus miniseries space war Calendar Food Network Tarantino YA Marathons TCA Lifetime NYCC Rom-Com Disney streaming service sports based on movie Infographic El Rey Pride Month SundanceTV 2019 richard e. Grant elevated horror Apple TV+ Sundance Now Lifetime Christmas movies Tumblr Apple crime drama movies Mystery Character Guide Writers Guild of America video MCU Women's History Month GIFs cinemax halloween Turner screen actors guild DC streaming service VH1 Emmy Nominations Biopics Fantasy Sci-Fi Masterpiece supernatural disaster Photos LGBTQ werewolf hist canceled TV shows Thanksgiving Reality festivals Animation OWN Superheroe cancelled television Nickelodeon latino 21st Century Fox Endgame spanish language tv talk what to watch series Shudder Peacock USA Music Mudbound Syfy cars Countdown Lucasfilm toy story theme song sag awards politics APB travel CNN Mindy Kaling kids south america The Witch streaming witnail Winners BBC WGN TNT book blockbuster Anna Paquin ABC Family BET Pop quibi FOX First Reviews romantic comedy 2018 Country TruTV biography historical drama finale GoT comics Comics on TV Turner Classic Movies zero dark thirty YouTube Premium anthology romance SDCC Arrowverse TV renewals diversity GLAAD Sony Pictures golden globes DC Comics HBO social media anime TCM Television Academy Classic Film New York Comic Con VICE FX sequel 20th Century Fox green book HBO Max harry potter E3 sitcom revenge breaking bad Star Trek cults dragons TV PaleyFest Rock composers binge cops renewed TV shows Vudu Ellie Kemper adaptation