EXCLUSIVE: Reformed Hollywood Wildman Robert Downey Jr. Reveals His Favorite Roles — From Working With 'Mad Genius' Director to Raunchy Threeway Film
Robert Downey Jr. is one of the most successful actors of his generation.
April 23 2025, Published 6:30 p.m. ET
Robert Downey Jr. once had a reputation as one of the hardest partyers in Hollywood.
RadarOnline.com previously reported The Iron Man star said he first smoked pot – with his father – when he was just eight, and by the time he reached adulthood he was a full-blown addict.
Downey, now 60, confessed to graduating to harder drugs, smoking heroin and freebasing cocaine, which led to a string of arrests.
He served a six-month court-ordered stint in rehab in 1996, but after a 1998 parole violation, he was sentenced to six months in prison followed by another mandatory stint in treatment.
In 2001, he was busted again and ordered into a year-long recovery program which helped him finally get sober for good. He credited never giving up as the key to finally kicking the habit.
Now he's one of Hollywood's biggest success stories – not to mention highest paid stars – thanks to some of his favorite big and little screen roles.
'Less Than Zero' (1987)
Downey played a drug addict in one of his earliest movies.
Downey drew from experience when he played drug addict Julian Wells in Less Than Zero. The film came at a time when Downey's life was dominated by illegal substances.
He has said before the film: "I took my drugs after work and on the weekends. The role was like the ghost of Christmas future.
"And then things changed. In some ways, I became an exaggeration of the character. That lasted far longer than it needed to last."
'Chaplin' (1992)
He earned rave reviews as Charlie Chaplin.
Downey was nominated for an Oscar for his portrayal of silent film star Charlie Chaplin in the legend's biopic.
"Chaplin was an absolute gift and a bear of a challenge for someone who was 25," he's previously reflected. "It was a role that terrified me. I didn’t know if I could pull it off.
"That fear pushed me to give everything I had. It taught me what acting could really be."
'Natural Born Killers' (1994)
Downey clashed with director Oliver Stone on the set.
Directed by Oliver Stone, Downey plays self-serving tabloid journalist Wayne Gale, who helps elevate a pair of lovers and mass-murderers to cult-hero status.
Downey said: "This was a precision executed three-ring circus ballet. You just want to feel like you’re making the directors happy. You don’t get that with Oliver Stone.
"He’d say, 'If you don’t get this scene right, you’re going to f------ ruin my movie.' He’s a mad genius."
'Two Girls and a Guy' (1997)
He was part of a love triangle in 'Two Girls and a Guy.'
Downey plays "the guy" to Heather Graham and Natasha Gregson Wagner's "two girls."
In one of the most memorable scenes from the movie, Downey sings You Don’t Know Me. He's said of that scene: "I've always liked singing and I always encourage people to do it.
"It’s fundamentally impossible for the human body to not to be able to produce, hold, carry and interact in complex ways with tones and music!"
'Ally McBeal' (2000)
Downey took his talents to the small screen for a stint on 'Ally McBeal.'
Downey joined the cast of the David E. Kelley dramedy at the start of the series fourth season, playing star Calista Flockhart's love interest Larry Paul.
However, producers were forced to write him off the hit show after his 2001 drug arrest.
He has since gone on to say he was "extremely grateful for the role, which came at his lowest moments.
"It was my rock bottom. That’s when my addictions were at their very worst."
'Kiss Kiss Bang Bang' (2005)
Downey was especially proud of this film.
Downey has said this film takes the cake: "Kiss Kiss Bang Bang is I think, in some ways, the best film I’ve ever done.
"At that point, I never played a character who was so overtly not intelligent but lovable. And Harry is kind of a dummy, and it was so freeing for me."
'Zodiac' (2007)
He went on the hunt for a legendary serial killer.
The film tells the story of the manhunt for the Zodiac Killer, a serial killer who terrorized the San Francisco Bay Area during the late 1960s and early 1970s
Playing troubled San Francisco reporter Paul Avery made Downey realize something truly important: “That’s what I would’ve become if I hadn’t stopped drinking and using, this kind of miserable old guy.
"Better to play it than to be it."
'Tropic Thunder' (2008)
Downey faced criticism for his controversial role.
Downey earned his second Oscar for playing an Australian method actor who undergoes a controversial "pigmentation alteration" surgery to temporarily darken his skin for his portrayal of a black character in a fake movie.
Although his performance was lauded, Downey would eventually be criticized for donning "blackface" in the Ben Stiller comedy.
But it was a chance "to hold up to nature, the insane self-involved hypocrisy of artists and what they think they’re allowed to do on occasion."
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'Avengers: Endgame' (2019)
Downey is credited for jumpstarting the Marvel Cinematic Universe.
Little has brought Downey more success – and more money – than his portrayal of Tony Stark in nine Marvel movies.
"Iron Man was more than a movie role for me," he's said. "It was a chance to prove to myself and the world that I could rise again.
"I owe so much of my career to that."
'Oppenheimer' (2023)
He was awarded an Oscar for the eventual Best Picture winner.
Downey would finally take home his first Academy Award for his portrayal of Atomic Energy Commission member Lewis Strauss, the nemesis of Cillian Murphy’s physicist J. Robert Oppenheimer.
He's called it "the best film I’ve ever been in" – and praised his devoted wife, Susan, for sticking with him in the worst of times.
"She found me, a snarling rescue pet, and loved me back to life. That’s why I am here," he said.
