8 Perfect Roles From Robert Downey Jr.’s Imperfect Career

Robert Downey Jr.

Robert Downey Jr. | Timothy Hiatt/Getty Images

Robert Downey Jr. may be one of the highest-paid actors in Hollywood according to Forbes, with a strong fanbase and critical acclaim for his roles, but his career hasn’t been without road bumps. It can be easy to forget that the Iron Man star was an acclaimed film actor known for serious roles in films like the Charlie Chaplin biopic Chaplin before his struggles with drug addiction nearly ended his career by making filmmakers afraid to invest in the erratic actor.

Here’s a look at some of RDJ’s most memorable film roles, both before and after his sobriety and Hollywood comeback.

1. Less Than Zero

Less Than Zero

Less Than Zero | 20th Century Fox

Downey first rose to fame as a young actor as a member of the Brat Pack in the 1980s. His best performance from that period and when he first began to be taken seriously was his role as a drug addict in the 1987 drama Less Than Zero. His take on a rich L.A. boy who loses everything to drugs hit pretty close to home for the actor, who would struggle with drug addiction for most of his life.

While the movie itself got very mixed reviews, with a 54% rating on Rotten Tomatoes, Downey’s performance was almost universally praised. “Mr. Downey gives a performance that is desperately moving,” said a review from The New York Times. Overall it doesn’t do the Bret Easton Ellis novel that it’s loosely adapted from justice, but it’s worth watching if you’re a fan.

2. Chaplin


Chaplin | TriStar Pictures

Downey earned his first Oscar nomination for this biopic about the legendary silent filmmaker and star Charlie Chaplin. The actor extensively prepared for the role by learning to do things left-handed and working with a choreographer to mimic Chaplin’s signature mannerisms, according to an article from The New York Times.

Some criticized the movie for taking liberties with the events in Chaplin’s life, but Downey’s portrayal of the film legend was universally acclaimed. Director Richard Attenborough was so confident in Downey’s ability to disappear into the character that he even included some archival footage of the actual Chaplin at the end of the movie.

3. Ally McBeal

Ally McBeal

Ally McBeal | Fox

Downey’s recurring role on the popular legal drama Ally McBeal was his first attempt at a comeback after one of his early, unsuccessful stints at rehab. He took the role of star Calista Flockhart’s love interest after finishing a stretch in prison in 2000 and instantly received acclaim for his performance, including a Golden Globe award for best supporting actor. But after facing two more drug arrests, his character was written off the show and he was fired.

Downey himself isn’t much of a fan of his performance on the show and said in an interview with The Guardian, “I’m probably not the best person to ask about that period. It was my lowest point in terms of addictions. At that stage, I didn’t give a fuck whether I ever acted again.”

4. Kiss Kiss Bang Bang

Kiss Kiss Bang Bang

Kiss Kiss Bang Bang | Warner Bros.

This 2005 film is a tongue-in-cheek look at the hardboiled crime genre and is one of the biggest films of Downey’s early comeback. After the actor finally found lasting sobriety, he had a slow time returning to acting as producers had to take big risks on him due to his previous behavior. Downey’s close friend Mel Gibson personally paid his insurance bond so that he could participate in the first film of his comeback, The Singing Detective. The producer of the thriller Gothika agreed to take a salary cut until production was complete in case Downey’s addictive behavior should become a problem.

In Kiss Kiss Bang Bang, Downey plays a petty burglar who ends up accidentally auditioning for and landing a role in a Hollywood film. Critics praised the movie’s dark humor and the chemistry between lead actors Downey and Val Kilmer. The film also stars a young Michelle Monaghan. The movie has become a bit of a cult classic that many feel is underrated.

5. Iron Man

Iron Man

Iron Man | Marvel/Disney

Downey has said landing the role in Kiss Kiss Bang Bang was what gave Iron Man director Jon Favreau the confidence to cast him in the mega-budget Marvel movie. His performance as the spoiled rich weapons-maker Tony Stark earned raves from fans of the original comic books and from film critics. Downey managed to make the character funny, charming, arrogant, and somehow likeable.

The Iron Man franchise has been one of Marvel’s most successful enterprises, with the third installment being one of the highest-grossing movies of all time according to Box Office Mojo. That draw is almost solely based on Downey’s appeal in the lead role. Iron Man is the film that turned the actor into the major Hollywood star that people had been saying he had the potential to be for over 20 years.

6. Tropic Thunder

Tropic Thunder

Tropic Thunder | DreamWorks Pictures

While Iron Man was all fun and games, right after completing the first in the film series that would make him a worldwide star, Downey made this comedy in which he plays a soldier wearing blackface and earned himself his second Academy Award nomination. Tropic Thunder is an action-comedy satire co-starring Ben Stiller and Jack Black.

The movie is about a group of actors who go to Vietnam to shoot a war film but end up being ditched by their director when he grows tired of their behavior. They then must rely on their acting skills to survive in the violent remote jungle that’s controlled by a drug cartel.

Downey’s character is an insane method actor who got skin pigmentation to play an African American soldier and refuses to break that character no matter what happens to the team. While some were offended by Downey’s character being in blackface, the part was really meant as a way to lampoon the great lengths some method actors go to in order to play a role.

Downey has said his take on the character was inspired by famous method actors like Daniel Day-Lewis and Russell Crowe, according to an article from ComingSoon. Following up Iron Man with this critical darling in the same year was enough to cement RDJ’s comeback.

7. Sherlock Holmes

Sherlock Holmes

Sherlock Holmes | Warner Bros.

The next franchise Downey decided to pick was Guy Ritchie’s take on Sherlock Holmes. While this hasn’t proven as popular with fans or critics as the BBC’s recent Benedict Cumberbatch-starring TV miniseries based on Arthur Conan Doyle’s stories, it still made over $200 million domestically when it came out, according to Box Office Mojo, mostly based on the draw of Downey.

He ended up winning a Golden Globe for the role and overall the movie got decent reviews for the performances from Downey as Holmes and Jude Law as Dr. Watson.

8. The Avengers

The Avengers

The Avengers | Marvel/Disney

Downey has reprised the Iron Man/Tony Stark role multiple times, having played the character in three Iron Man films and two Avengers movies thus far. That 2012 film pulled together many of the heroes from various Marvel franchises and packed fans into theaters.

It also got great reviews, with a 92% rating on Rotten Tomatoes. That said, the movie raised the bar for superhero films in general and managed to balance being entertaining with creating smart, realistic characters out of the iconic superheroes.