For eight seasons, Entourage brought us the fictionalized career of Vincent Chase (Adrian Grenier), who started out in Mentos commercials and ended up becoming one of the biggest stars in Hollywood. Along the way, we witnessed the highs and lows of Vincent’s career, which included everything from disastrous indie sets to his work with some of the industry’s most important directors.
With this week’s premiere of the highly-anticipated Entourage movie, Vinnie Chase finally makes his way to the big screen for the first time. For real. As Vincent, Turtle, E, Drama and Ari become movie stars themselves, let’s take a look back at the ten best fictional projects from Vincent Chase’s career so far.
10. Medellin (2007)
Medellin started out as a passion project for Vincent Chase and his manager/best friend Eric Murphy, but ended up becoming a gigantic debacle that Vincent had to spend seasons digging himself out of. The story of Pablo Escobar was supposed to be Vincent’s Scarface, but instead ended up killing his career. Medellin kind of looks like the makeup department responsible Big Momma’s House worked on a terrible version of Steven Sodebergh’s Che. Or, as The Chicago Sun-Times critic Richard Roeper said, “It “makes [Vincent] look like the love child of Jiminy Glick and a case of Twinkies.”
After getting booed at Cannes, the film lost its proposed purchase for $75 million and was instead bought for $1 and sent direct-to-DVD. Sure, getting booed at Cannes didn’t hurt The Tree of Life, Taxi Driver or Inglourious Basterds, but Medellin looked like a start-to-finish disaster. One-time up-and-comer director Billy Walsh lost his mind, a documentary was filmed about the problematic making of the film and Vincent earned a Razzie nomination for Worst Actor. After watching the trailer, it looks like maybe $1 was too much to pay for this bomb.
9. Chinese Energy Drink Commercial (2005)
Yes, somehow even this commercial is better than Medellin.
While struggling to find his latest project, Vincent made this China-only commercial, for which he received half a million dollars. This commercial is the only Vincent project we actually get to see in its entirety (unless you count A Walk to Remember) and it’s about as ridiculous as you’d imagine. The drink doesn’t even have an actual name, the director’s name is the borderline-offensive Chang Chung and the drink’s tagline is “Good till your heart explodes!” While Vincent does his best/. pretending to be the commercial’s hero, it’s Vincent’s brother Johnny that steals the show with a cameo that allows him to help his baby bro out for once.
8. Head On (2004)
When we first meet up with the titular entourage, they are awaiting the release of Vincent’s first starring role in Head On. Vincent co-starred with another “It actor” of the time, a pre-Fantastic Four Jessica Alba. Critics denounced the project, saying that “Vincent Chase is guilty of fraud” and that he “makes walking and talking look difficult.” Head On was beat at the box office by an animated film about a squirrel, but even though it doesn’t sound all that good, having been called a “by-the-number crime thriller,” everyone has to start somewhere.
7. The Takeover (2011)
Thanks to director Nick Cassavetes’ insistence that Vincent do his own stunts and an injury that followed, The Takeover caused Vincent to sort of lose his mind in Season Seven. Vincent started thrill-seeking, driving a motorcycle, dating a porn star and eventually getting arrested for cocaine. The Takeover’s sole purpose was really to propel Vincent on this downward spiral, and it seemed like a strange production as well. For example, Cassavetes is an odd choice for an action director, since the closest he’s gotten to this genre is probably John Q. and The Takeover would’ve been his next project after My Sister’s Keeper. Vincent later went on to say that the movie would probably suck anyway, but to be fair, he did also think being the lead in a Benji movie could be a good idea.
6. Ferrari (2010)
Shooting for Ferrari began right as Vincent’s career was back on its upswing. While the creation of the film happens off-screen and we never see any footage, it doesn’t actually sound half bad. This biopic of Enzo Ferrari is directed by The Shawshank Redemption’s Frank Darabont and…that’s pretty much all that’s said about it. We also know that Vincent had to bribe his driver’s instructor to get his license for the project, but Ferrari unfortunately gets lost in the Gatsby afterglow, even though it does seem pretty decent.
5. Smoke Jumpers (2008)
Smoke Jumpers was supposed to represent Vincent’s return to the spotlight after the Medellin debacle, but ended up becoming its own problematic production. Written by two first-time screenwriters, Vincent was meant to play a supporting role—perhaps a good choice after Medellin—but his costar Jason Patric stole almost all of his lines at the request of director Verner Vollstedt, a thinly-veiled take on Werner Herzog. Smoke Jumpers was never released, ultimately costing Warner Bros. $120 million dollars, but to be honest, Smoke Jumpers is the first film on this list that sounds like it could’ve actually been good. The movie centered on the story of about nine firefighters fighting the greatest forest fire ever in Oregon, and was also supposed to star Edward Norton. The combining of the egos of Norton and a Herzog-type would’ve at the very least been interesting and the material would’ve fallen right into the Herzog wheelhouse.
4. Aquaman (2006)
Now that we’ve seen how badass Jason Momoa looks as the star of the upcoming Aquaman movie, Adrian Grenier seems like a ridiculous choice. But consider this—Aquaman would’ve come out in an era when Tobey freaking Maguire was the world’s biggest superhero. The project would not only would become Vincent’s biggest movie, but also the highest-grossing film OF ALL TIME. A $116 million dollar first weekend—the biggest opening of all time—means that Aquaman would’ve made over $600 million. Considering the movie would’ve been James Cameron’s first film since Titanic, these numbers don’t seem that strange. However, what does seem strange is that Aquaman was penned by Andrew Kevin Walker, whose past credits include darker films like Se7en and Sleepy Hollow, which doesn’t exactly match Cameron’s style or the material we see from Aquaman. But ultimately, a big-budget adaptation of this Justice League character from Cameron, co-starring Mandy Moore and James Woods does sound like a fascinating idea, even if the one scene we do see makes it look pretty terrible.
3. Air-Walker (2013)
While Entourage ended before we could see what became of Air-Walker, the potential this film had would’ve probably made it Vincent’s biggest, and his second superhero film. Based on the character created by Stan Lee and scheduled for release in summer 2013, Air-Walker could’ve technically set him up as a recurring character throughout the Marvel universe. And since Air-Walker is a villain, this would’ve given Vincent one of his darkest roles. While Secretariat director Randall Wallace walked off the project after Vincent’s decision not to take a drug test, this actually turned out to be blessing, as the film would go to Friday Night Lights’ Peter Berg.
2. Queens Boulevard (2005)
With Queens Boulevard, Vincent received his first taste of critical success and proved that sometimes choosing the project you really want is a better move than taking on the project that you probably should do. Queens Boulevard introduced the crew to Billy Walsh (which would later prove to be unfortunate) and took Vincent to Sundance for the first time. The film also had a quiet release on DVD, after both Billy and Vincent proclaimed the studio ruined the film by taking the black-and-white film and colorizing it. But for a small indie drama for which Vincent only received $60,000, Queens Boulevard had a pretty remarkable cast, with Ethan Suplee, Zooey Deschanel and even Robert Duvall. The filmmight have been ruined in the long run, but the original version sounds like it could’ve been damn good.
1. Gatsby (2009)
After the disaster that was Medellin and the implosion of Smoke Jumpers, Vincent really needed a win. Thankfully, Gus Van Sant saw some of the footage from Smoke Jumpers, showed Vincent’s scenes to Martin Scorsese and landed him in the auteur’s latest film, an adaptation of “The Great Gatsby” simply titled Gatsby. For once, the fake film created by Entourage actually sounds better than the films it trying to mimic.
A look at the Gatsby mockup poster shows us that the film reunited Scorsese with his screenwriter from The Departed, William Monahan. Not only that, but the cast for Gatsby is incredible, with John C. Reilly, Vera Farmiga, Emily Blunt, Natalie Portman (as Daisy Buchanan) and assumedly Ryan Gosling at Gatsby. The only thing that doesn’t quite make sense is Vincent playing the part of Nick Carraway. If anything, he’s much more the Gatsby type. Still, Scorsese’s modern adaptation would’ve likely been better than Baz Luhrmann’s take on the story and with that cast and crew, it absolutely sounds like the best Vincent Chase movie by far.
Ross Bonaime is a D.C.-based freelance writer and regular contributor to Paste. You can follow him on Twitter.