As much as I enjoyed the wish-fulfillment fantasy of hanging out with Vincent Chase and his boys, my favorite aspect of Entourage was its searing satire of the sorry state of Hollywood. Much like Seth Rogen’s The Studio, Entourage highlights the absurdity of the movie business by having petty rivalries and legal loopholes get in the way of real creativity and artistic integrity.
Billy Walsh can create a beautiful black-and-white movie like Queens Boulevard, and the distributor can butcher and bastardize it into a colorized monstrosity. Vince can turn a superhero blockbuster like Aquaman into the highest-grossing movie ever made, and still get squeezed out of the sequel because he fell out with a studio head. In all that anarchy, sometimes you make a great movie.
James Cameron’s Aquaman
Vinnie’s first blockbuster starring vehicle was an Aquaman movie directed by James Cameron. Cameron has never directed a superhero movie, but since almost all his movies involve water, Aquaman seems right up his alley. This was before the MCU, when Sam Raimi’s Spider-Man movies and Bryan Singer’s X-Men movies were still laying the groundwork for modern superhero films.
Every James Cameron movie is an event. This is the guy who made Terminator, Terminator 2, Aliens, Titanic, Avatar — everything he touches turns to gold. Even when he makes a rare misstep, like the muddled and repetitive Avatar: Fire and Ash, it’s still a spectacle to behold on the big screen. Cameron’s Aquaman movie would be something else.
Head On
Head On was one of Vince’s earliest starring roles after his breakout turn in A Walk to Remember. It’s the latest movie that Vince is promoting when we first meet him in season 1, so we don’t know much about it. But it seems to be the kind of star-driven mid-budget original thriller that doesn’t really get made anymore, and I always welcome those kinds of movies making a comeback.
Queens Boulevard
Vince’s first project with regular collaborator Billy Walsh is the movie that put both of them on the map. It established Vincent as a genuinely talented actor, not just a pretty movie star, and it put Billy on every list of up-and-coming directors to watch (although, after Medellin, he would be bumped off those lists and sent straight to director jail).
The distributor butchered the film by colorizing it, adding a Hollywood gloss to what was once a gritty underground drama. The original black-and-white version, true to Billy’s vision, was described (by Billy himself) as his Mean Streets. Whether that’s true or not, I’d love to see it. “I am Queens Boulevard.”
Smoke Jumpers
Smoke Jumpers was shut down and remained unfinished after a falling-out between Vince and his egomaniacal director, Verner Vollstedt, a thinly veiled Werner Herzog-type perfectionist played by Stellan Skarsgård. After Verner gave Vince contradictory directions and handed off his lines to the other actors, Vince made a scene and Verner fired him.
We don’t know much about Smoke Jumpers, but we do know the structure of the script, and it sounds like a solid disaster movie. The final third of the film shows the firefighter protagonists fighting the biggest fire of their careers, but the first two-thirds would follow those characters on the night before the fire, so the audience would have a chance to get to know them before their lives are in danger.
Frank Darabont’s Ferrari
Long before Michael Mann directed Adam Driver in an Enzo Ferrari biopic, Frank Darabont was making one with Vinnie Chase. Mann’s Ferrari movie is a dull, dreary, melodramatic affair, but Darabont’s sounds like it would’ve been a faster, zippier, more action-packed driving movie, like Ford v Ferrari or Vanishing Point (and that would be a lot more fun to watch).
Air-Walker
Entourage is the only show on television with the guts to put Stan Lee and Sasha Grey in the same room. Vince’s involvement in Lee’s Air-Walker superhero franchise unfortunately coincided with his spiral into drug addiction. Director Randall Wallace quickly deduces that Vince is on cocaine, and Lee recognizes Vince’s girlfriend from her adult film career, so the project promptly falls apart.
But it would’ve been interesting to see Vince’s take on Air-Walker. On paper, it might sound similar to Aquaman, but it’s the opposite. Aquaman is a traditional superhero, but Air-Walker is a villain, so it would’ve been one of Vinnie’s darkest roles.
Medellin
Vince and Billy’s follow-up to Queens Boulevard, an epic biopic of Pablo Escobar, was one of the most troubled productions in Hollywood history. It went overbudget and overschedule, it got rewritten and retooled to oblivion, and it got too big for its own good. Things looked up when it got into Cannes, but it was booed at its festival premiere, leading to a humiliating $1 sale to Harvey Weingard.
Even if Medellin is a total mess, it would be a fun mess to watch. It’s always fascinating to see an ambitious cinematic vision that got out of control, whether it’s Heaven’s Gate or Beau is Afraid. Billy Walsh’s vision of a Scarface-style gangster epic must be a sight to behold.
I Wanna Be Sedated
The billion-dollar blockbuster success of Bohemian Rhapsody has led to Hollywood studios pumping out biopics on just about every musical legend you can think of: Bob Dylan, Bob Marley, Elvis Presley, Michael Jackson. Entourage predicted this craze when Vince was up for a lead role in a Ramones biopic called I Wanna Be Sedated.
In a world where we just got a biopic of a Neil Diamond tribute act, I’m surprised we haven’t seen a Ramones biopic yet. They’re legends of punk rock, and their story would make for an appropriately anarchic odyssey through the highs and lows of the music industry.
Silo
After being hired to adapt a novel called Head in the Clouds into a screenplay, Billy Walsh turned in a draft that had absolutely nothing in common with the book. At least Charlie Kaufman’s meta script-within-a-script for Adaptation did attempt to adapt The Orchid Thief; Silo was a completely new story.
But Vince read it and decided he wanted to do that movie even more than Head in the Clouds. Silo apparently revolves around a couple of farmers being stranded on a mountain in 2075, and I’m already hooked just from that elevator pitch. Silo sounds like a precursor to chilling post-apocalyptic thrillers like Snowpiercer and, well, Silo.
Martin Scorsese’s Gatsby
Out of all the fake movies that were either developed or produced throughout Entourage’s eight-season run, the one I really wish was actually a movie is Martin Scorsese’s Gatsby. In the world of Entourage, Scorsese cast Vince as Nick Carraway in a movie version of The Great Gatsby set in modern-day New York.
The Great Gatsby is the perfect source material for Scorsese. It has the old-timey elegance of The Age of Innocence, the brooding antiheroes of Goodfellas, and the class warfare themes of The Wolf of Wall Street. Baz Luhrmann did a lavish Great Gatsby movie a few years later, but it wasn’t the same.