After popping up in a diverse selection of movies in the 90s (Swingers, Jurassic Park 2, a Psycho remake), Vince Vaughn became a household name in the early 2000s when he began collaborating with a group of comedic actors that the media irritatingly dubbed “the Frat Pack.†(Don’t blame me, I wasn’t part of the media yet when that term was coined). This group, which also contained folks like Will Ferrell, Ben Stiller, and Owen Wilson, dominated the big-screen comedy industry in the pre-Apatow era, with Vaughn and his buddies constantly popping up in each other’s films. While this comedy clique doesn’t seem quite as tight as it was five years ago, its members still find the time to work together every now and then. This week sees the release of The Watch, which reunites Vince Vaughn with frequent costar Ben Stiller (and also stars Apatow protégé Jonah Hill and UK import Richard Ayoade).
Let’s take a look at some of Vince Vaughn’s projects that never happened, whether they be movies he auditioned for but didn’t get, roles he flat-out turned down, or projects that fell apart altogether. Vaughn has played fast-talking wiseasses in dozens of films, but he didn’t get the chance to play a fast-talking wiseass in a sequel to Old School, as the title role in Donnie Darko, or in a western about a Hasidic Jew starring Jon Favreau.
Dazed and Confused (1993)
The role: Benny O’Donnell
Who got it: Cole Hauser
A 22-year-old Vince Vaughn auditioned for the part of tough high school football player Benny O’Donnell in Richard Linklater’s coming-of-age classic Dazed and Confused. Linklater rejected Vaughn, though, because he felt he looked too much like Ben Affleck, who had already been cast. It sounds weird to think of Affleck and Vaughn looking alike, but they resembled each other a lot more closely in the early 90s:
There’s Something about Mary (1998)
The role: Pat Healy
Who got it: Matt Dillon
Vince Vaughn was amongst the actors the Farrelly Brothers considered to play the sleazy private eye in Something About Mary. Along with Cuba Gooding Jr. and Bill Murray, Vaughn was up for the part, but the  Farrellys wound up choosing Matt Dillon instead.
Donnie Darko (2001)
The role: Donnie Darko
Who got it: Jake Gyllenhaal
Despite the fact that he was in his early 30s at the time, Vince Vaughn was offered the lead role (of a troubled teenager) in Donnie Darko. Vaughn turned the part down because he felt he was too old. The part went to Jake Gyllenhaal, who was 19 at the time of production and therefore a much more believable teenager than Vince Vaughn.
Old School Dos (in development circa 2006)
The role: Bernard “Beanie†Campbell
Old School is one of Vince Vaughn’s most popular movies ever, and in 2006, Todd Phillips and Scot Armtrong began writing a sequel, titled Old School Dos. Will Ferrell, however, was not as excited about the movie as some of the others from the original, telling the press “I read [the script]. Some super funny set pieces, but I don’t know. I think Vince [Vaughn] had the same reaction. We’re just kind of doing the same thing again. It was like us going to Spring Break, but we’ve got to find this guy who’s the head of a fraternity. Once again, funny things but it’s just us once again back in a fraternity setting. It just felt like it was repeating. But watch, I’m overthinking it.†Todd Phillips has now moved on to his The Hangover series, which the main trio of actors feels very comfortable sequelizing.
David O. Russell’s The H-Man Cometh (in development circa 2006)
The role: Hume Stevens
In 2006, Vince Vaughn signed on to star opposite Elizabeth Banks in a film for director David O. Russell called The H-Man Cometh. In H-Man, which was co-written by Russell, Vaughn was to play a sarcastic host of a radio call-in show who starts taking on the qualities of his callers. The project fell apart, freeing Vaughn up to make Fred Claus.
Speed Racer (2008)
The role: Racer X
Who got it: Matthew Fox
Before the Wachowskis got their hands on the Speed Racer movie rights, Vince Vaughn spearheaded a live-action film based on the classic Japanese animated series. In 2004, Vaughn signed on to play the title character’s mysterious older brother Racer X and to also produce the film. Vaughn told the press, “I’ve been a fan of the show since I was a kid and always liked the theme of the protective older brother who can’t reveal his identity.†Two years later, the Wachowskis signed on to write and direct the movie and Vince Vaughn stopped being involved.
The Green Hornet (2011)
The role: Britt Reid/The Green Hornet
Who got it: Seth Rogen
Michel Gondry originally signed on to direct The Green Hornet back in 1997 and wanted Vince Vaughn for the lead role (despite the studio offering it to Mark Wahlberg). Gondry and Robocop screenwriter Edward Neumeier started working on a script, but they had creative differences with the studio and the project was shelved. Kevin Smith tried to get a Green Hornet movie going a few years later with Jake Gyllenhaal, but Seth Rogen actually pulled it off and Michel Gondry returned to direct him in 2011’s The Green Hornet.
Other movies that Vince Vaughn almost played a cocky smartass in:
No Place Like Home (circa 2003) – Vaughn would have played a smug smart aleck who loses everything after a breakup and has to move back in with his parents.
The Marshal of Revelation (circa 2003) – Vaughn would have played a lewd wise guy sidekick to Jon Favreau who would have played a Hasidic Jew gunfighter in the Old West. Vaughn and Favreau have been working on this one since the mid-90s and still hope to someday get the movie made.
Hamlet Unzipped (circa 2004) – Vaughn would have played a fast-talking know-it-all in this modernized adaptation of the Shakespeare play.
Heckled (circa 2004) – Vaughn would have played a brash loudmouth in this comedy about a heckler who causes an NBC player’s suspension but soon finds himself the roles reversed.
Realtors (circa 2007) – Vaughn would have played an overconfident chatterbox in this black comedy about competing real estate agents.
Sunny and 68 (circa 2008) – Vaughn would have played a haughty blowhard who’s a star in the pro poker world until he loses everything, which leads him to reconnect with his terminally ill mother and his five-year-old daughter in what is clearly a serious drama.
Male Doula (circa 2009) - Vaughn would have played a bombastic motormouth who finds his passion as a child labor coach after being dumped by a woman who lied about being pregnant with his baby.
2 Guns (circa 2010) – Vaughn would have played a chatty hotshot in this action-comedy about a pair of undercover lawmen tasked with investigating each other. Owen Wilson was considering playing the other lead role, but the movie’s been reworked as a vehicle for Mark Wahlberg and Denzel Washington.
The Insane Laws (circa 2011) - Vaughn would have played a wise-cracking windbag who is lifelong friends with another dude (Jason Bateman) until their kids fall in love. Jim Carrey and Alec Baldwin recently signed on to the project, meaning Vaughn and Bateman are out.
Bradford Evans is a writer living in Los Angeles.