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Robert Downey Jr.’s best roles, from Chaplin to Sherlock Holmes

One of the most popular actors of his generation, Robert Downey Jr. has had a lengthy film career. He first appeared on screen as a child in Pound, a film directed by his father, Robert Downey Sr., in 1970, and slowly but surely rose to become an A-list star. He’s had trials and tribulations along the way, including a well-publicized battle with drug abuse, but also one of the most applause-worthy comebacks of any Hollywood actor.

With two Academy Award nominations under his belt, Downey Jr. might not yet have won one yet, but he can take consolation in the fact that he starred in the top-grossing film franchise of all time. He topped Forbes’ list of highest-paid actors in Hollywood for three consecutive years, from 2013 to 2015, and he’s also one of the highest-grossing box-office stars in the world. With impressive skills to turn from drama to comedy on a dime, he has played some iconic roles over the last few decades. Here are some of his best.

10) Leo Wiggins (Johnny Be Good)

Leo Wiggins
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Downey plays the best friend of lead character Johnny (Anthony Michael Hall), a top high-school quarterback who’s being courted by every school imaginable. Leo is on hand to provide comic relief and standard best friend ribbing. “Do you think the colleges would want you so much if they knew you were afraid of the dark?” his character jokes in one scene. The 1988 film is ’80s teen comedy personified, and though it was a box office bomb with an embarrassing 0% rating on Rotten Tomatoes, it has become a cult hit thanks, in part, to one of RDJ’s most memorable early roles.

9) Paul Avery (Zodiac)

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Downey Jr. plays crime reporter Paul Avery, who is reluctant to listen to political cartoonist Robert Graysmith (Jake Gyllenhaal) and his theories about the real-life Zodiac Killer. Gyllenhaal is the star of this 2007 film, but RDJ makes an impact with his raw performance as a man who obsesses over a case he can’t crack.

8) Julian Wells (Less Than Zero)

Less Than Zero
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The 1987 drama, loosely based on a Bret Easton Ellis novel of the same name, stars Andrew McCarthy as a college freshman and Downey Jr. as his drug-addicted friend in one of his most heralded roles. The character was a little too close to home for the actor, who was quoted as calling Julian the “Ghost of Christmas Future.” The character was initially an exaggeration of himself, but he eventually became an exaggerated version of the character in real life. It’s no surprise that many critics were enthralled with the performance. The New York Times’ Janet Maslin referred to it as “desperately moving.”

7) Sherlock Holmes (Sherlock Holmes)

Sherlock Holmes
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Many an actor has played the iconic Sir Arthur Conan Doyle character, but in this 2009 period action film, directed by Guy Ritchie, Downey Jr. put his own spin on things. He received almost universal praise for the portrayal and won a Golden Globe. The film itself received a pair of Academy Award nominations for Best Original Score and Best Art Direction. RDJ reprised the role for a second film in 2011 and is set to appear again as the scientist/eccentric detective in Sherlock Holmes 3, which is rumored to be released in 2021.

6) Ian (Weird Science)

Weird Science
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This 1985 John Hughes teen comedy/sci-fi film follows two nerdy kids who create a gorgeous virtual woman who ends up coming to life. The film is a cult classic, featuring Downey Jr. as Ian, a popular bully who relentlessly torments the geeky kids (remember that iconic Slurpee scene?). The film solidified RDJ’s position as a member of the 1980s Brat Pack.

5) Larry Paul (Ally McBeal)

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Switching to the small screen, this role put Downey Jr. back on the map after falling on hard times as an actor due to his longtime substance abuse issues. He earned the role of Calista Flockhart’s love interest on the legal comedy/drama, and was welcomed back to the industry with an Emmy nomination and a Golden Globe win.

4) Charlie Chaplin (Chaplin)

Chaplin
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This 1992 biographical film about the British comic actor who defined the silent film generation was a tall order for the young actor. While the film itself received generally mixed reviews, with many criticizing the screenwriting, Downey Jr.’s performance received plenty of praise as he embodied the legendary silent film star.

3) Harry Lockhart (Kiss Kiss Bang Bang)

Kiss Kiss Bang Bang
Warner Bros. Pictures

In this 2005 neo-noir/black comedy film partially based on the novel Bodies Are Where You Find Them, Downey Jr. plays a thief who hides out at an acting audition to evade police and ends up being trained in detective work by a real detective. Critics have raved about the performance, calling it everything from one of his most enjoyable, to a “quicksilver delight,” and his rapport with co-star Val Kilmer is well worth the price of admission.

2) Kirk Lazarus (Tropic Thunder)

Tropic Thunder
Image via Pramount Pictures

Few imagined that this 2008 action/comedy directed by Ben Stiller, about a group of spoiled actors who are dropped into the middle of a jungle by their frustrated director, would have performed so well at the box office, much less received an Academy Award nomination. That nomination went to Downey Jr. for his role as Kirk Lazarus, an Australian method actor who has his skin pigment darkened in order to portray a black man. He refuses to break character, despite the fact that they aren’t filming. He’s truly hilarious in the film, which showcases his tremendous range.

1) Iron Man/Tony Stark (MCU)

Iron Man/Tony Stark
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In his biggest (and best) role of his career, Downey Jr. has played Tony Stark (aka Iron Man) in 11 MCU movies over the same number of years, starting with Iron Man in 2008 and ending with Avengers: Endgame. All the films have been massive box-office successes and catapulted the actor’s career to superstardom. Taking on one of Marvel’s lesser-known heroes (to mainstream audiences, anyway), the actor helped build the entire foundation of the Marvel Cinematic Universe and helped keep it rolling throughout its historic run. We can’t imagine anyone else as the wealthy, brilliant, and cocky scientist/superhero.

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Christine Persaud
Christine has decades of experience in trade and consumer journalism. While she started her career writing exclusively about…
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