The Lost Roles of Owen Wilson

Actor. Writer. Guy with a funny-looking nose. Owen Wilson is a multi-hyphenate who has the rare ability to balance diverse projects, from quirky Wes Anderson indies (Bottle Rocket) to goofy buddy flicks (Shanghai Noon), big budget disaster movies (Armageddon) to bawdy mainstream comedies (Wedding Crashers). Wilson’s writing talents aren’t to be slighted either. He earned an Oscar nomination in 2002 for co-authoring The Royal Tenenbaums with Wes Anderson, and the pair also scripted Bottle Rocket and Rushmore together. Wilson is still going strong, with his new movie, The Big Year, a bird-watching comedy that also stars Steve Martin and Jack Black, opening tomorrow.

Over the course of his fifteen-year career, Owen Wilson has had a number of roles he missed out on, dropped out of, and a slew of projects that fell apart completely. Below is a collection of the “lost roles” of Owen Wilson, including numerous failed attempts to recreate the magic of Wedding Crashers by casting him opposite Vince Vaughn, the Dan Harmon TV series that would have seen him voicing a talking motorcycle, and a role that would have required him to catch his prop penis in a zipper, leaving it looking like the misshapen protuberance on his face. Alright, I promise no more jokes about Owen Wilson’s nose for the rest of this article. That’s my vow to you, readers!

Making Amends (in development, mid-90’s)

In the mid-90’s, Judd Apatow began developing Making Amends, a comedy that would have starred Owen Wilson and Rip Torn and featured a musical score by Warren Zevon. In Making Amends, Wilson, who had just made his mainstream movie debut with a small part in the Apatow production The Cable Guy, was to play a recovering alcoholic making up for his past wrongs. The movie was never greenlit, likely because Wilson was practically an unknown actor at this point. Making Amends is said to have been Judd Apatow’s Jerry Maguire, and it could have given his career, as well as that of Owen Wilson, a big boost early on.

There’s Something About Mary (1998)

The role: Ted Stroehmann

Who got it: Ben Stiller

During Something About Mary’s casting process, the studio was reluctant to hire Ben Stiller, who was not a widely-known actor at the time, as the film’s lead. The Farrelly Brothers suggested another up-and-comer for the part, Owen Wilson, causing the studio to suddenly become comfortable with hiring Ben Stiller because Wilson was even less recognizable to audiences than Stiller. If Owen Wilson had landed this part, his career very well may have flipped with Ben Stiller’s, turning him into a major movie star first instead of things happening in the opposite order. Mary was Stiller’s breakthrough movie role, allowing him to become a major force in mainstream comedy in the years that followed. Wilson didn’t become a household name until a couple of years later, but he was able to focus on his writing projects with Wes Anderson like Rushmore and The Royal Tenenbaums. Tenenbaums was the last movie Wilson scripted, since he became too busy with his burgeoning movie career to focus on screenwriting. If he’d broken through as an actor a little earlier, it might have prevented Rushmore and Tenenbaums from coming to be in the ways they did, as well as Wes Anderson’s ascendance to indie darling status.

Heat Vision and Jack (unsold TV pilot, 1999)

The role: Heat Vision (voice only)

Two years after his aborted Apatow project, Owen Wilson teamed up with a few more respected comedy auteurs, Dan Harmon, Rob Schrab, and Ben Stiller, to provide the voice for a talking motorcycle in the pilot to Heat Vision and Jack, an absurdist riff on cheesy 80’s shows like Knight Rider. The Fox network didn’t order Heat Vision to series, but the pilot, which also stars Jack Black, Christine Taylor, and Ron Silver, went on to develop a cult following.

Ocean’s Eleven (2001)

The role: Virgil Malloy

Who got it: Casey Affleck

Owen and sibling Luke Wilson were set to play the Malloy Brothers in this wildly-popular heist movie remake, but they dropped out to make Royal Tenenbaums. Director Steven Soderbergh tried to get the Coen Brothers (yes, those Coen Brothers) for the parts and then went to filmmaking duo Mark and Michael Polish (Twin Falls Idaho) when the Coens were unavailable. When that didn’t pan out, he gave up on the idea of casting two brothers completely and hired non-siblings Casey Affleck and Scott Caan. Ocean’s Eleven was a huge hit, and it could have helped the careers of the Wilson brothers, but they were both off making successful films on their own at this point. By the time the sequels rolled around, Owen and Luke Wilson would have been too big to reprise these supporting roles.

Stealing Harvard (2002)

The role: Walter “Duff” Duffy

Who got it: Tom Green

In 2000, Owen Wilson was in talks to play the sidekick in this quickly-forgotten comedy about a guy who turns to crime so that he can keep his promise to pay for his niece’s Ivy League education. Wilson dropped out, and Tom Green jumped in to take his place. Given that Owen Wilson’s career was on the rise in at this point, it makes sense that he wouldn’t have wanted to play second fiddle to a less-famous, pre-My Name is Earl Jason Lee, but maybe a bigger name would have signed on for the lead role if Wilson had stayed onboard.

I Now Pronounce You Chuck & Larry (2007)

The role: Chuck Levine

Who got it: Adam Sandler

Long before Chuck and Larry ever got into the hands of Adam Sandler and his cohorts, respected indie duo Jim Taylor & Alexander Payne (Election, About Schmidt) were hired to rewrite the script. David Dobkin, who had just directed Owen Wilson and Vince Vaughn in Wedding Crashers, was looking to recreate that film’s success by reuniting Wilson and Vaughn onscreen. Wilson and Vaughn were briefly linked to Chuck & Larry, but they soon moved on, along with Dobkin. Jim Taylor and Alexander Payne’s script fell into the hands of Adam Sandler and pal Dennis Dugan who had it completely rewritten into a gay panic-laced, lowbrow affair. Taylor and Payne still received writing credit on the finished product, but they’ve disowned I Know Pronounce You Chuck & Larry and said that the movie was completely different from what they had written. If the Owen Wilson-Vince Vaughn version had stuck to Taylor and Payne’s script, it would have been a much classier, more tactful, and intelligent film.

Tropic Thunder (2008)

The role: Rick Peck

Who got it: Matthew McConaughey

Owen Wilson was originally cast as Ben Stiller’s character’s sleazy agent, Rick Peck, in Tropic Thunder, but he was forced to leave the project after being hospitalized due to a failed suicide attempt. Thankfully, Wilson recovered and went back to acting soon thereafter. It would have been nice to see Owen Wilson star with Ben Stiller in Tropic Thunder, but these two have worked together a zillion times anyway, and McConaughey did fine with the tiny part he was given.

Mr. Popper’s Penguins (2011)

The role: Mr. Popper

Who got it: Jim Carrey

Before Jim Carrey signed on to co-star with a bunch of penguins in this family film, Ben Stiller was attached to play the lead role with his Greenberg buddy Noah Baumbach directing. Stiller and Baumbach left the project over “creative differences.” Their version of the movie was different than the finished product, with Stiller’s character balancing his penguin problems with his duties as Peyton Manning’s publicist. Jim Carrey, Owen Wilson and Jack Black were considered to replace Stiller, but director Mark Waters went with Carrey. With Jim Carrey as its lead, Mr. Popper’s Penguins performed poorly with critics and audiences, but who knows how it would have done with another actor in the lead role? Audience interest in Jim Carrey movies has been waning in recent years, while Wilson, Stiller, and Black have all been faring a little better lately. With any of them playing Mr. Popper, the film might have turned out more successful.

The Secret Life of Walter Mitty (currently in development)

The role: Walter Mitty

Who got it: Ben Stiller (for now)

Along with just about every major comedic actor in the past ten years, Owen Wilson was once close to starring in The Secret Life of Walter Mitty, a fantasy comedy based on the classic James Thurber story about a man who has elaborate daydreams. Wilson, Sacha Baron Cohen, Mike Myers, Will Ferrell, Jim Carrey were all at one point circling the project, with Steven Spielberg, Ron Howard, and Gore Verbinski eyeing the director’s chair. The project is currently in the hands of Ben Stiller, who plans to direct and star. We’ll see how long it takes before Stiller plays hot potato and passes Walter Mitty to Adam Sandler or Jason Bateman. They probably feel left out because they’re two of the only comic actors going who’ve never been offered this role.

Other unproduced projects:

  • Eastbound and Down (in development circa 2001) – Not to be confused with the Danny McBride HBO series of the same name, the movie Eastbound and Down was proposed as  a modern retelling of Smokey and the Bandit with Owen Wilson playing the titular bandit. Brent Forrester, who’s been a writer on just about every hip comedy in the past two decades (The Simpsons, King of the Hill, Undeclared, Ben Stiller Show, The Office), was brought on board to pen the script, but Eastbound and Down never made it into production.
  • The Smoker (in development circa 2004) – Based on the short story by David Schickler, The Smoker follows a female student at a private high school who falls in love with her teacher and brings him home for dinner, only for her parents to ask him to marry her. Owen Wilson was going to star as the teacher, with Natalie Portman portraying the high schooler. Richard Linklater signed on to direct from a script by David Schickler and Peter Tolan, but the movie was cancelled and everyone involved moved on.
  • Hello to All That (in development circa 2005) – Owen Wilson bought up the rights to journalist John Falk’s book, Hello to All That: A Memoir of War, Zoloft, and Peace, which tells Falk’s true story about how, while extremely depressed, he became a reporter in Bosnia’s Civil War in the early 90’s. Wilson intended to star in the movie, but the production has yet to get off the ground.
  • Outsourced (in development circa 2004-07) – From director Hank Azaria, Outsourced was a proposed reteaming of Wedding Crashers duo Owen Wilson and Vince Vaughn. The film would have starred Wilson and Vaughn as two best friends who work at a factory in Southern California who move to Mexico when their jobs are outsourced there, quickly becoming labor leaders south of the border. Vaughn and Wilson backed out, and Azaria never got the movie going without them.
  • 2 Guns (currently in development) – Another proposed Owen Wilson-Vince Vaughn reunion, 2 Guns, is still being developed, even though the two of them have vacated the project. Mark Wahlberg is currently attached to star in the action-comedy, which follows “an undercover DEA agent and naval intelligence officer who, without knowing it, are investigating each other for stealing from the mob.”
  • Bradford Evans is a writer living in Los Angeles.

    The Lost Roles of Owen Wilson