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.

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