7.The Singing Detective(2003)
Many people don’t know this movie, but it’s actually pretty fun and super weird. Robert Downey Jr. stars as a writer who’s suffering from a debilitating skin disease and unable to move. To entertain himself, he begins to hallucinate musical numbers and gets super paranoid.
Even though the numbers are all lip-syncing, they’re still fun to watch, and the song choices are ironic and entertaining. It also stars Robin Wright, Mel Gibson, and Alfre Woodard.
6.Less Than Zero(1987)
WhileLess Than Zerocan be hard to watch, it’s another great example of Robert Downey Jr.’s acting range. He plays a drug addict and puts in a superbly captivating performance—but it’s one of those movies you might only be able to watch once.
The movie had a bad influence and actually contributed to pushing him further into substance addiction at the time. It’s almost like we’re watching what he suffered later on.
Related:Trippy drug movies that depict psychedelic experiences
5.Kiss Kiss Bang Bang(2005)
Kiss Kiss Bang Bangis just so much fun to watch. Val Kilmer and Robert Downey Jr. have a ton of chemistry on screen, and that’s just scratching the surface of what’s great here.
The movie features a murder mystery where Downey Jr. plays a thief-turned-actor who meets a detective (played by Kilmer) who convinces him to help in a murder investigation.
4.Chances Are
If you’re looking for Robert Downey Jr. in one of his best earlier roles, check outChances Are(in which he’s only a couple years older than he was inLess Than Zero.) He already possessed such star quality back then, not to mention growing into his handsomeness.
The movie is about a man who dies and is then reincarnated. He isn’t supposed to remember his past life, but he does—and all sorts of problems come up because of it.
For example, it turns out the girl he’s dating was his daughter in his past life. He switches gears and sets his sights on his former wife, who’s super confused. His best friend from his past life is in love with his former wife, so things are a complete mess.
Watching the characters find their ways out of it is a good time. It’s a funny and entertaining movie that highlights his comedic timing.
3.Only You(1994)
Only Youis a romantic comedy that features Marisa Tomei as an engaged teacher who feels like she’s still seeking out her soulmate—all because of a name given to her by both Ouija board and fortune teller.
She gets an unexpected phone call from someone by that name and embarks on a crazy adventure to Italy with her best friend (played by Bonnie Hunt) to find him. While there, she falls in love with Robert Downey Jr.’s character. It’s as fun as it sounds!
Related:The best romantic comedy movies on Amazon Prime Video
2.Heart and Souls(1993)
Heart and Soulsis a fun comedy with Robert Downey Jr. playing a young man who can see a certain set of ghosts because he’s meant to help them with their unfinished business.
Watching Downey Jr. shift and adapt when those spirits enter his body is a sight to behold, and the truest highlights of the movie. He can capture their essences with such precise humor. Downey Jr. has even claimed this as one of his favorite works.
Another significant part of this film is witnessing how well he sings when he sings the national anthem! It’s an excellent preview of future roles that involve his singing.
1.Chaplin(1992)
Robert Downey Jr. is completely brilliant in his portrayal of Charlie Chaplin in this 1992 movie. In fact, many people easily forget that he was nominated for an Academy Award for his role here.
This epic biopic is long and involved, which provides him a stage to properly showcase his range of acting skills. He fully embodies Charlie Chaplin—to the point that even Chaplin’s real daughter, Geraldine, was awestruck at how much Downey Jr. embodied her father. She was too stunned the first time she saw him in full costume even to speak.
To prepare for this role, Downey Jr. watched all of Chaplin’s movies, learned to play both violin and tennis left-handed, and worked with a coach to help him get the mannerisms and posture just right.
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