Offered slyly comic supporting turn as a homosexual book editor in "Wonder Boys"
Played a method actor who portrays an African American character in the Ben Stiller directed comedy "Tropic Thunder"; earned Golden Globe, SAG and Academy Award nominations for Best Supporting Actor
Played the gay husband of a documentary filmmaker in Toback's "Black & White"
Starred in James Toback's "Two Girls and a Guy" with Natasha Gregson Wagner and Heather Graham
Reprised his role as Tony Stark in "Avengers: Age of Ultron"
Appeared in the video for Elton John's recording of "I Want Love"
First feature released, "Baby, It's You"
Cast in a recurring role on "Ally McBeal" (Fox) as a love interest to the title character; fired from show in April 2001 after being arrested yet again for drug use; earned Emmy nomination in 2001 for Supporting Actor in a Comedy Series
Starred in the George Clooney-directed "Goodnight, and Good Luck" a 1950s-era drama that chronicles broadcaster Edward R. Murrow's campaign to bring down Senator Joseph McCarthy
Teamed with Mel Gibson in "Air America"
TV-movie debut in "Mussolini: The Untold Story" (NBC) as the Italian dictator's son Bruno
Was a regular cast member of "Saturday Night Live" (NBC)
Appeared as James Woods' associate in "True Believer"
Cast as Earl Rivers in "Richard III"; Annette Bening played his sister
Feature acting debut, "America"; directed by his father (released theatrically in 1986)
Formed production company Herd of Turtles
Played journalist Paul Avery in David Fincher's serial killer thriller "Zodiac"
Played the lead role of Tony Stark, a playboy billionaire weapons manufacturer of Marvel Comcis' "Iron Man"
Anchored the documentary "The Last Party" about the U.S. Presidential campaign
Displayed his gifts as a romantic lead opposite Marisa Tomei in "Only You"
First starring role in James Toback's "The Pick-Up Artist"
Headlined "Restoration" (filmed in 1994) portraying the court physician to King Charles II
Portrayed Charlie Chaplin in Richard Attenborough's biopic "Chaplin"; received a Best Actor Oscar nomination
Re-teamed with Jon Favreau to reprise the role of Tony Stark for "Iron Man 2"
Reunited with Altman as supporting player in "The Gingerbread Man"
Starred in "A Scanner Darkly," a rotoscoped film by director Richard Linklater
Co-starred in the supernatural thiller "Gothika" opposite Halle Berry and Penélope Cruz
Delivered amusing turn as a young TV producer in the satirical "Soapdish"
First screen appearance in his father's "Pound" (uncredited)
Landed featured role in Robert Altman's "Short Cuts"
Offered a strong supporting turn as an crack addict in "Less Than Zero"
Played <i>Los Angeles Times</i> columnist Steve Lopez in "The Soloist"
Played an Australian TV tabloid journalist in Oliver Stone's "Natural Born Killers"
Played the title role in Guy Ritchie's reimagining of "Sherlock Holmes"; earned a Golden Globe nomination for Best Actor
Portrayed an AIDS-stricken gay man in Mike Figgis' "One Night Stand"
Starred in the murder mystery "Kiss, Kiss, Bang, Bang" with Val Kilmer and Michelle Monaghan
Starred in the remake of "The Singing Detective"; film adapted from the acclaimed Dennis Potter-scripted British miniseries
Co-starred in the Todd Phillips' comedy "Due Date"
Reprised role in Guy Ritchie's sequel "Sherlock Holmes: A Game of Shadows"
Returned to the Marvel Cinematic Universe for "Iron Man 3," reprising the role of Tony Stark/Iron Man.
Appeared alongside Robert Duvall in "The Judge"
Co-starred in the Marvel superhero ensemble feature "The Avengers" as Tony Stark/Iron Man
Known for such albums as "The Futurist"
Reprised Iron Man role in "Captain America: Civil War"
Again played Tony Stark / Iron Man in Marvel's "Spider-Man: Homecoming"