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He worked on several occasions with the comedy troupe Stella (Michael Ian Black, Michael Showalter and David Wain), making cameo appearances in their short films and eponymous TV series.Rockwell played Victor Mancini in the film Choke (2008), based on the novel by Chuck Palahniuk.In addition to big-budget feature films, Rockwell also appears in indie films such as The F Word and he played a randy, Halloween-costume-clad Batman in a short, Robin's Big Date, opposite Justin Long as Robin.He also starred in the film Snow Angels (2008) opposite Kate Beckinsale.Rockwell has also received positive notices for his role opposite Nicolas Cage in Ridley Scott's Matchstick Men (2003), with Entertainment Weekly calling him "destined by a kind of excessive interestingness to forever be a colorful sidekick." He received somewhat more mixed reviews as Zaphod Beeblebrox in the film version of The Hitchhiker's Guide to the Galaxy (2005).He then had a notable supporting role as Charley Ford, brother of Casey Affleck's character Robert Ford, in the well-received drama The Assassination of Jesse James by the Coward Robert Ford (2007), in which Brad Pitt played the lead role of Jesse James.

The film was produced by Kevin Walsh, Nat Faxon, and Jim Rash, marking Rockwell's second collaboration with all three.

According to an interview on The Howard Stern Show, director Jon Favreau considered casting him as the titular character in Iron Man as the studio was initially hesitant to work with Robert Downey Jr., who had been considered for his role in The Hitchhiker's Guide to the Galaxy.

Rockwell appeared in the Iron Man sequel, released in 2010, as Tony Stark's rival weapons developer, Justin Hammer.

Critic Roger Ebert said of his performance that he "seems to have become the latter-day version of Christopher Walken – not all the time, but when you need him, he's your go-to guy for weirdness." In 2007, Rockwell guest-starred in the web series Casted: The Continuing Chronicles of Derek Riffchyn, Greatest Casting Director in the World. He appears opposite Jonathan Togo as Derek and Justin Long as Scott.

Rockwell plays an aspiring young actor named Pete Sampras.

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