1. Chaplin (1992). Director: Richard Attenborough. Downey Jr. won a Golden Globe Award for Best Actor – Motion Picture Musical or Comedy for his performance as Charlie Chaplin.
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2. Tropic Thunder (2008). Director: Ben Stiller. Downey Jr. won a Golden Globe Award for Best Actor – Motion Picture Musical or Comedy and was nominated for an Academy Award for Best Supporting Actor for his performance as Kirk Lazarus.
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3. Zodiac (2007). Director: David Fincher. Downey Jr. received critical acclaim for his performance as Robert Graysmith, the San Francisco Chronicle cartoonist who investigated the Zodiac Killer.
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4. The Iron Man trilogy (2008, 2010, 2013). Director: Jon Favreau. Downey Jr. played Tony Stark, the billionaire playboy who becomes Iron Man, in this popular superhero franchise.
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5. The Avengers (2012). Director: Joss Whedon. Downey Jr. reprised his role as Tony Stark in this crossover film that brought together the Avengers, a team of superheroes.
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6. Avengers: Age of Ultron (2015). Director: Joss Whedon. Downey Jr. again played Tony Stark in this sequel to The Avengers.
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7. Captain America: Civil War (2016). Director: Anthony Russo and Joe Russo. Downey Jr. reprised his role as Tony Stark in this film, which pitted the Avengers against each other.
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8. Spider-Man: Homecoming (2017). Director: Jon Watts. Downey Jr. made a cameo appearance as Tony Stark in this film, which introduced Tom Holland as Spider-Man.
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9. Avengers: Infinity War (2018). Directors: Anthony Russo and Joe Russo. Downey Jr. returned as Tony Stark in this film, which saw the Avengers battle Thanos.
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10. Avengers: Endgame (2019). Directors: Anthony Russo and Joe Russo. Downey Jr. played Tony Stark for the final time in this film, which saw the Avengers defeat Thanos.
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