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Robert Downey Jr.’s 10 Greatest Roles (Ranked)

Plus, besides his past performances, the newly minted Oscar winner is now playing four different characters in ‘The Sympathizer’


spinner image Robert Downey Jr. in HBO series The Sympathizer, in his Iron Man suit in the film "Avengers: Endgame" and in the film Zodiac
(Left to right) Robert Downey Jr. in "The Sympathizer"; as Tony Stark/Iron Man in "Avengers: Endgame"; as Paul Avery in "Zodiac."
Photo Collage: AARP; (Source: Beth Dubber/HBO; Walt Disney Studios Motion Pictures/Marvel Studios/courtesy Everett Collection; Paramount/courtesy Everett Collection)

Robert Downey Jr., 59, who won his first Oscar for Oppenheimer, has an almost chameleonic gift for disappearing into a dizzying variety of roles – from screen legend Charlie Chaplin to Marvel superhero Iron Man. In the new HBO drama series The Sympathizer, based on a Pulitzer Prize-winning novel, Downey plays no less than four different characters, each involved in the story of the Vietcong spy protagonist (Hoa Xuande): a shady CIA operative at the end of the Vietnam War, a professor, a right-wing congressman who sounds suspiciously like Dirty Harry-era Clint Eastwood, and a narcissistic Hollywood director. That beats Peter Sellers playing three different roles in Dr. Strangelove.

It’s a bravura turn for a star who has racked up many highlights on his increasingly impressive résumé. Let’s take a look at Downey’s 10 best performances over the years.

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spinner image Robert Downey Junior and Patricia Clarkson in a scene from the film Good Night and Good Luck
(Left to right) Robert Downey Jr. and Patricia Clarkson in "Good Night, and Good Luck."
Warner Independent Pictures/courtesy Everett Collection

10. Joe Wershba, Good Night, and Good Luck (2005)

Downey is best known for his outsize performances, but he went the opposite way in this fact-based drama from director George Clooney. In this story set during the Red Scare of the 1950s, Downey plays a CBS reporter working for David Strathairn’s Edward R. Murrow, who has his own secret he wants to maintain: his marriage to a colleague (Patricia Clarkson). His magnetic understatement stands out.

 Watch it: on Apple TV, Prime Video

spinner image Robert Downey Jr., Alfre Woodard and Kyra Sedgwick sitting together in a scene from the film Heart and Souls
(Left to right) Robert Downey Jr., Alfre Woodard and Kyra Sedgwick in "Heart and Souls."
Universal Pictures/courtesy Everett Collection

9. Thomas Reilly, Heart and Souls (1993)

Remember that 1984 movie All of Me, in which Steve Martin played a lawyer whose body is magically inhabited by Lily Tomlin’s dying millionaire? Well, Downey four-upped Martin in this underrated comedy, playing a guy whose body is invaded by the souls of four different dead people stuck in postmortal limbo: from a skeevy Tom Sizemore to a sultry Kyra Sedgwick to a typically put-upon Charles Grodin. In one hilarious scene, he pivots between all four lost souls while trying to keep a crucial boardroom presentation on track.

Watch it: DVD on Amazon

spinner image Calista Flockhart and Robert Downey Jr. standing behind a snowman in the television series Ally McBeal
(Left to right) Calista Flockhart and Robert Downey Jr. in "Ally McBeal."
Courtesy Everett Collection

8. Larry Paul, Ally McBeal (2001)

Downey joined the fourth season of the legal dramedy Ally McBeal as a lawyer whom Calista Flockhart’s Ally initially mistakes for a therapist. Before long, witty banter and romantic sparks are flying between the two – though Downey’s time on the series was cut short after his 2001 arrest on drug charges. He later admitted that he was in the throes of a serious addiction while working on the show – but still managed to pull off an impressive performance that earned him a Golden Globe award and an Emmy nomination.

Watch it: on Disney+, Prime Video

7. David Seton Barnes, Soapdish (1991)

Downey was already a veteran of late 1980s teen fare like Weird Science and Johnny Be Good when he nabbed a role in this Sally Field comedy about the behind-the-scenes shenanigans at a fictional soap opera. And he nearly walks off the film as a slimy young producer who schemes with a wannabe starlet (the hilarious Cathy Moriarty) to replace Sally Field’s character as the show’s longtime grande dame.

Watch it: on Max

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6. Paul Avery, Zodiac (2007)

David Fincher’s thriller about the hunt for the so-called Zodiac Killer who terrorized the Bay Area in the late ’60s and early ’70s is another underrated gem. In his first postrehab starring role (alongside Jake Gyllenhaal and Mark Ruffalo), Downey plays a newspaper reporter whose confident façade erodes when the killer begins to threaten him. In a devastatingly authentic art-imitates-life twist, we also watch his character fall deeper into an alcoholic haze amid his inability to crack the case.

Watch it: on Paramount+

Note: Paramount+ provides a discount to AARP members and pays AARP a royalty for the use of its intellectual property.

5. Harry Lockhart, Kiss Kiss, Bang Bang (2005)

After his well-publicized stint in rehab, Downey began his Hollywood comeback in this darkly comedic neo-noir with a witty script by writer-director Shane Black. Downey plays to type as a small-time crook who heads to Hollywood with his longtime crush (Michelle Monaghan) and a private investigator (Val Kilmer) hired to prep him for a studio screen test. Downey fires one-liners like bullets from a Gatling gun, making you wish that he and Kilmer had made a whole series of buddy detective movies together.

Watch it: on Apple TV, Prime Video

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4. Lewis Strauss, Oppenheimer (2023)

Downey finally won Oscar gold in Christopher Nolan’s three-hour drama as a bureaucratic villain who seeks to strip J. Robert Oppenheimer of his security clearances when he begins showing regret about the nuclear arms race resulting from his work. Almost unrecognizable with his retreating gray hair and browline glasses, the actor holds the snark in check to play a man whose pettiness reveals the dark side of power.

Watch it: on Peacock

3. Kirk Lazarus, Tropic Thunder (2008)

It’s hard to imagine any other actor in this century who could get away with blackface – let alone earn an Oscar nomination for doing it. But Downey went all-in as a craven Australian actor who goes deep Method to play a Black staff sergeant in Vietnam. He surgically dyes his skin, gets a fresh scalp of kinky hair and sinks into a full-jive accent that he won’t drop even when the cameras stop rolling. It’s a fully committed performance – one that would get most actors committed to Hollywood jail. Downey’s unwavering commitment to the bit also helps to ground a comedy steeped in absurdity.

Watch it: on Paramount+

2. Charlie Chaplin, Chaplin (1992)

Downey scored his first Oscar nomination in the title role in Richard Attenborough’s biopic of the silent-film star. Despite a rather conventional script, Downey turns in a riveting central performance – nailing both Chaplin’s British accent as well as his distinctive mannerisms (and walking style) while convincingly playing the actor from youth to old age. Plus, Downey did all his own stunts.

Watch it: on Paramount+

1. Tony Stark, Iron Man, Iron Man through Avengers: Endgame (2008-2019)

There were doubters who said that American audiences would never embrace a superhero like Iron Man, known only to comic book die-hards before Downey donned the metallic red suit and made the character a pop culture phenomenon. Given his well-publicized past, the actor had to audition for the role. But can you imagine anyone else making this franchise a hit? He nailed the persona of an arrogant billionaire who was quick with a quip but ultimately willing to stick out his neck to save humanity – a first-class jerk you can’t help but root to succeed.

Watch it: on Disney+

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