The Pickup Artist (1987)
Molly Ringwald is a fiercely independent city woman with a bit of a Mafia problem—which Downey, as a serial dater who finds love, finds himself wrapped up in.
Less Than Zero (1987)
Downey poured himself into the character of Julian, a lovable flower of a guy weighed down by addiction, at a time when he was struggling with the same illness in real life. An astonishing, powerful performance.
Chaplin (1992)
His first Oscar nomination (damn that Al Pacino), for a part he was born to play.
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Natural Born Killers (1994)
In Oliver Stone’s wild, dark satire about our media-obsessed culture, Downey plays a smarmy, sensationalizing tabloid-TV journalist who helps turn two serial killers into stars.
Home for the Holidays (1995)
Director Jodie Foster cast Downey in this wrenching, very funny family drama set over one torturous Thanksgiving. Most of the funny comes from Downey, and most of the heart comes from the relationship between Downey’s Tommy and his sister Claudia, played by Holly Hunter. “We kind of rewrote the film for Robert,” Foster says.
Two Girls and a Guy (1997)
More smarmy Downey. A movie that looks like a stage play about a two-timing New Yorker who returns to his fabulous loft one day only to be confronted by the two women (Heather Graham and Natasha Gregson Wagner). And because it’s Downey, by the end the smarm melts away and you love him.
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Kiss Kiss Bang Bang (2005)
One of Downey’s favorite Robert Downey Jr. movies—a quirky, cool L.A. crime story that is also one of the best buddy comedies (the other buddy being a vintage Val Kilmer) of this century.
Tropic Thunder (2008)
Oscar nomination number two, for his performance as an actor bent on winning an Oscar by playing a Black man in a war movie. Both the movie and his performance are hilarious and brilliant.
Iron Man (2008)
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Due Date (2010)
Pairing Downey with Zach Galifianakis is casting gold. “There’s something about Robert that I think makes you always want to root for him, even when he's on top of the world,” director Todd Phillips told Esquire.
Sherlock Holmes: A Game of Shadows (2011)
You can’t lose, but the second film of this fast-paced, imaginative Guy Ritchie–directed franchise is the best—so far. Number three is in preproduction.
Sr. (2022)
A moving documentary about Downey’s dad that, at its heart, explores the strained, beautiful relationship between a father and a son, both with their demons.
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Oppenheimer (2023)
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