He started high school at theRuth Asawa San Francisco School of the Arts[6] withMargaret Cho andAisha Tyler, but received his high school diploma from Urban Pioneers, anOutward Bound-stylealternative school. Rockwell explained, "I just wanted to get stoned, flirt with girls, go to parties." The school "had a reputation as a place stoners went because it was easy to graduate."[7] The school helped him regain an interest in performing. After appearing in anindependent film during his senior year, he moved to New York to pursue an acting career.[8] He later enrolled in the Professional Actor Training Program at theWilliam Esper Studio in New York.[9]
After his debut role in the controversialhorror filmClownhouse in 1989, which he filmed while living in San Francisco, he moved to New York and trained at theWilliam Esper Studios with teacher William Esper.[10] Rockwell went on to say: "It was great. We shot at Coppola's house. I didn't know anything about acting ... It was fun."[11] His career slowly gained momentum in the early 1990s, when he alternated between small-screen guest spots in TV series likeThe Equalizer,NYPD Blue andLaw & Order and small roles in films such asLast Exit to Brooklyn andTeenage Mutant Ninja Turtles. He also appeared as the title character inThe Search for One-eye Jimmy (1994). During this time, Rockwell worked in restaurants as a busboy and delivered burritos by bicycle.[12] At one point, Rockwell worked as aprivate detective's assistant. "I tailed a chick who was having an affair and took pictures of her at this motel", he toldRolling Stone in 2002. "It was pretty sleazy." A well-payingMiller commercial in 1994 finally allowed him to pursue acting full-time.
The turning point in Rockwell's career wasTom DiCillo's filmBox of Moonlight (1996), in which he played an eccentric man-child who dresses likeDavy Crockett and lives in an isolated mobile home. The ensuing acclaim put him front and center with casting agents and newfound fans alike, with Rockwell himself acknowledging that "That film was definitely a turning point... I was sort of put on some independent film map after 10 years in New York."[8] Rockwell later elaborated: "People saw it at Sundance and it got me a lot of attention ... It led toLawn Dogs, andSafe Men, andJerry and Tom."[11]
He then received strong reviews for the filmLawn Dogs (1997), where he played a working-class lawn mower who befriends a wealthy 10-year-old girl (Mischa Barton) in an upper-classgated community inKentucky; Rockwell's performance won him Best Actor honors at both theMontreal World Film Festival and theCatalan International Film Festival. In 1999, Rockwell played the deranged prisoner William "Wild Bill" Wharton in theStephen King prison dramaThe Green Mile. At the time of the film's shooting, Rockwell explained why he was attracted to playing such unlikable characters. He said, "I like that dark stuff. I think heroes should be flawed. There's a bit of self-loathing in there, and a bit of anger... But after this, I've really got to play some lawyers, or a Britisharistocrat, or they'llput a label on me."[4]
After appearances as a bumbling actor in the science fiction parodyGalaxy Quest (1999). Rockwell went on to say: "Who doesn't love that fucking movie, right?"[11] He also playedFrancis Flute in theShakespeare adaptationA Midsummer Night's Dream (1999), and gregarious villain Eric Knox inCharlie's Angels (2000), Rockwell won the then-biggest leading role of his career asThe Gong Show hostChuck Barris inGeorge Clooney's directorial debut,Confessions of a Dangerous Mind (2002). Rockwell's performance was well-received, and the film earned generally positive reviews. "That is a great movie. George (Clooney) really taught me to be simple and not like put too much in there."[11]
Rockwell also received positive notices for his role oppositeNicolas Cage inRidley Scott'sMatchstick Men (2003), withEntertainment Weekly calling him "destined by a kind of excessive interestingness to forever be a colorful sidekick."[13] Rockwell went on to say: "Matchstick Men was really fun. Had a lot of fun with Nic (Cage). Alison Lohman, incredible. Bruce McGill. Ridley Scott ... He's really cool ... He let us really go ... he let us fuck around with that. (Producers) would never make that movie for that amount of money now (in 2026). We had nice trailers and we got paid."[11] He received somewhat more mixed reviews asZaphod Beeblebrox in the film version ofThe Hitchhiker's Guide to the Galaxy (2005). About the film, Rockwell said: "Not fun really... it's all the kind of stuff Jim Carrey and Eddie Murphy did very well... Those puppets were phenomenal and the sets were incredible."[11] He then had a notable supporting role as Charley Ford, brother ofCasey Affleck's characterRobert Ford, in the well-received dramaThe Assassination of Jesse James by the Coward Robert Ford (2007), in whichBrad Pitt played the lead role ofJesse James. About taking on the role, Rockwell revealed: "I didn't want to do that movie initially but then I was glad I did it because it was such a great movie."[11] According to an interview onThe Howard Stern Show, directorJon Favreau considered casting him as the titular character inIron Man as the studio was initially hesitant to work withRobert Downey Jr., who had been considered for his role inThe Hitchhiker's Guide to the Galaxy. Rockwell eventually appeared inIron Man 2, released in 2010, asTony Stark's rival weapons developer,Justin Hammer.
In addition to big-budget feature films, Rockwell has also appeared inindie films such asThe F Word and played a randy, Halloween-costume-cladBatman in ashort,Robin's Big Date, oppositeJustin Long asRobin. He also starred in the filmSnow Angels (2008) oppositeKate Beckinsale. Rockwell said about the movie: "That's a good one ... I think David allowed me to do what I wanted to do ... David Gordon Green and I created this character together based on this book. It was a dark story and there was this documentary that Brad Pitt gave me about these born again Christians who blow up abortion clinics ... that was very helpful, watching that. It was a really cool movie to do."[11] He has worked on several occasions with the comedy troupeStella (Michael Ian Black,Michael Showalter andDavid Wain), making cameo appearances in theirshort films andeponymous TV series.
Rockwell played Victor Mancini in the filmChoke (2008), based on the novel byChuck Palahniuk. CriticRoger Ebert said of his performance that he "seems to have become the latter-day version ofChristopher Walken – not all the time, but when you need him, he's your go-to guy for weirdness."[14]
Rockwell at the 2009 Tribeca Film Festival forMoon
In 2007, Rockwell guest-starred in the web seriesCasted: The Continuing Chronicles of Derek Riffchyn, Greatest Casting Director in the World. Ever. He appears oppositeJonathan Togo as Derek andJustin Long as Scott. Rockwell plays an aspiring young actor named Pete Sampras.[15] In 2009, he starred in the critically acclaimed science fiction filmMoon, directed byDuncan Jones. His performance as a lonely astronaut on a long-term solo mission to the Moon was widely praised, with some critics calling for anAcademy Award for Best Actor nomination.[16] Rockwell went on to say about playing the duel roles: "The trick of (playing opposite yourself) is you can be your own director and have control over the scene because you're playing both parts ... That's a trick I've seen done well a couple of times ... Jeremy Irons inDead Ringers, I watched that quite a bit and I watchedMidnight Cowboys."[11] On May 3, 2010, it was announced that Rockwell would team up again withIron Man 2 directorJon Favreau for Favreau'sadaptation of the graphic novelCowboys & Aliens. He played a bar owner named Doc who joins in the pursuit of the aliens.[17]
Rockwell also had key roles inMartin McDonagh'sSeven Psychopaths (2012),[18] andNat Faxon andJim Rash'sThe Way, Way Back (2013).[19] For his performance inThe Way, Way Back, some critics felt he again deserved anAcademy Award nomination.[20][21] He went on to say: "Oh man, I love that movie. That's a fun movie. We were ab-libbing. That's essentially Bill Murray inMeatballs - I mean, that's the character."[11]
In January 2014, it was announced that Rockwell was cast inThe Eel, in which he played an escaped convict. The film was produced by Kevin Walsh, Nat Faxon, and Jim Rash, marking Rockwell's second collaboration with all three.[22] Additionally, in 2015 Rockwell starred in two films,remake ofPoltergeist andMr. Right.Mr. Right is about an ex-CIA agent turned hitman who gained a conscience and turned the tables on those that hired him as a hitman. He was also brutally honest with his girlfriend, portrayed byAnna Kendrick, on what he does. She then turns herself into a hitwoman. On May 3, 2016, it was announced that Rockwell would voice Mortimer Ramsey in the action video gameDishonored 2. Rockwell was cast along with otherMarvel Cinematic Universe actors.[23]
Rockwell has never been married, and said in a 2007 interview, "I definitely don't want to become a parent. It's not my bag."[36] He has been in a long-term relationship with actressLeslie Bibb since 2007. They met in Los Angeles while he was filmingFrost/Nixon.[37] Rockwell and Bibb appeared together inIron Man 2,Don Verdean, andThe White Lotus.[38][39]
In 2013, Rockwell gotlyme disease and had to be briefly hospitalized.[40]
