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At the time of the film's shooting, Rockwell explained why he was attracted to playing such unlikeable characters. But after this, I've really got to play some lawyers, or a British aristocrat, or they'll put a label on me." After appearances as a bumbling actor in 1999's science fiction satire Galaxy Quest, in the 1999 Shakespeare adaptation A Midsummer Night's Dream as Flute, and as gregarious villain Eric Knox in Charlie's Angels (2000), Rockwell won the biggest leading role of his career as The Gong Show host Chuck Barris in George Clooney's 2002 directorial debut, Confessions of a Dangerous Mind.Rockwell's performance was well received, and the film received generally positive reviews.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, based on the novel by Chuck Palahniuk.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.He is known for his leading roles in Lawn Dogs (1997), Confessions of a Dangerous Mind (2002), Matchstick Men (2003), The Hitchhiker's Guide to the Galaxy (2005), Choke (2008), Moon (2009), Seven Psychopaths (2012), and Mr.Right (2015), as well as for his supporting roles in The Green Mile (1999), Galaxy Quest (1999), The Assassination of Jesse James (2007), Frost/Nixon (2008), Conviction (2010), Iron Man 2 (2010), Cowboys & Aliens (2011), The Way, Way Back (2013), Poltergeist (2015), and Three Billboards Outside Ebbing, Missouri (2017).
After his debut role in the 1989 horror film Clownhouse (produced by Francis Ford Coppola's production company), which he filmed when based in San Francisco, he moved to New York and trained at the William Esper Studios, with teacher Terry Knickerbocker.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 2005 film version of The Hitchhiker's Guide to the Galaxy.He then had a notable supporting role as Charley Ford, brother of Casey Affleck's character Robert Ford, in the well-received 2007 drama The Assassination of Jesse James by the Coward Robert Ford, in which Brad Pitt played the lead role of Jesse James.He is said to have accepted the role without reading the script.He had never heard of the character before he was contacted about the part, and was unaware that Hammer is an old man in the comic books.