There isn’t another actor working today who has had a career arc as interesting as that of Robert Downey Jr. His trajectory would be worthy of a critical study, even if it wasn’t for his incredible talent. Born the son of a cult filmmaker whose work had been favorited among niche cinephile circles, Downey became a late addition to the “Brat Pack” era when he began appearing in comedies like “The Pick-up Artist” and “Back to School.” He soon began to gravitate towards darker and more psychological roles, but even a gig on a network sitcom wasn’t enough to curb Downey’s addiction issues. Even before he spent a brief stint in prison, Downey’s talents weren’t enough to save him from being essentially unemployable.
It was one of the most bewildering decisions in Hollywood history when Kevin Feige and Jon Favreau settled on Downey to take on the role of Tony Stark in “Iron Man,” which was then considered to be a B-list hero when compared to “Spider-Man” and “X-Men.” Downey’s intent on being taken seriously again was absolute. He launched a superhero franchise that morphed into a cinematic universe, all whilst working with acclaimed directors again. It was after Downey starred in “Avengers: Endgame” (which briefly became the highest-grossing film of all-time) and won an Academy Award for “Oppenheimer” that he could have feasibly been proclaimed the new “King of Hollywood,” inheriting the throne from Clark Gable. Here are the best Robert Downey Jr. films, ranked.
10. Richard III (1995)
Modern Shakespearean adaptations can be controversial, as the words of “The Bard” don’t always fit a context removed from the era of their inception. However, the 1995 adaptation of “Richard III” that starred Sir Ian McKellen as the ruthless leader made a clever decision to portray an alternative history of the 1930s, in which a European fascist party threatened to dominate the world through ruthless political gains. Downey, then still considered to be a viable young star, is cast in the critical role of Rivers, a supporter of King Edward IV (John Wood) who runs afoul of Richard’s schemes.
It speaks to Downey’s range that, at a time in which his private issues were already well-known, he did not struggle to play a character of supposed integrity who pays the price for loyalty and ultimately becomes a martyr for his cause. While “Richard III” does not have any characters who are completely without sin, Downey offered the perspective of someone who at least seemed principled, in the sense that he adhered to wartime codes of chivalry. To see someone like Downey opposite a British stage legend like McKellen offered an electrifying energy to the adaptation. It won’t be their last film together, as both are slated to appear in “Avengers: Doomsday.”
9. Wonder Boys (2000)
“Wonder Boys” is an undersung masterpiece that didn’t get a fair shake when it first debuted, despite boasting an Oscar-winning original song from Bob Dylan. Michael Douglas stars as a beloved professor who is in the midst of an extended process of writing his next novel, despite finding a protege (Tobey Maguire) who might be his superior.
Downey could have played either role if he were a decade older or younger, but he is placed in between the two seismic actors in the part of an eccentric literary agent who is desperate for his client to actually start editing down the pages of prose that supposedly might become a book someday.
To play a potentially broad, flamboyant character in the midst of an otherwise understated campus drama was a bold move on Downey’s part, and he has just the right amount of eccentricity to elevate the film without ever taking it over. Curtis Hanson isn’t a director who is discussed often enough when listing the most reliable, consistent journeyman filmmakers of his era, and his ability to conjure such vivacious work from Downey, Douglas, and Maguire is reason enough to label him as an underrated talent who was ahead of his time.
8. Natural Born Killers (1994)
Oliver Stone and Quentin Tarantino are two filmmakers who seem to ignite controversy wherever they go, so it only makes sense that the one film that they made together would end up igniting some of the most inflammatory rhetoric of the ‘90s. Ironically, the film is such a modern-day interpretation of the “Bonnie & Clyde” story, because it mirrors Arthur Penn’s 1967 classic in more ways than one. Just as “Bonnie & Clyde” announced the anti-authoritarian sentiments of the New Hollywood era as studios handed over power to auteurs, “Natural Born Killers” emphasized the ‘90s independent boom through the collision of the most signature studio filmmaker and the industry’s hot-streak screenwriter.
While it’s Woody Harrelson and Juliette Lewis who star as the two central killers who embark on a ruthless, bloody odyssey, Downey is cast as an insipid reporter who ends up being seduced by their cult of violence. The implication of casting a former teen idol as the “angry young white man” who would use media violence as an inspiration was a brilliant decision on Stone’s part that made the film age even better in a post-Columbine era. The high-wire act between scathing satire and genuine terror is pulled off brilliantly by Downey.
7. Good Night, and Good Luck. (2005)
Downey sought respectability when he made his comeback, but he was also an actor’s actor who was highly praised by his peers. It made sense for him to take a supporting role within an awards-friendly ensemble drama about an important political subject, but “Good Night, and Good Luck” was also the second directorial effort of George Clooney, who made a habit of casting his friends. “Good Night, and Good Luck” is the story of Edward Murrow (David Strathairn), the CBS news reporter who faced persecution for daring to report on the ruthless policies of Senator Joseph McCarthy, who poisoned the democratic process by accusing his rivals of being secret Communists.
Although the film works hard to show the importance of every member of a news team, Downey is a standout as Joseph Wershba, a loyal correspondent who struggles with his responsibilities to journalism upon realizing that both he and his wife (Patricia Clarkson) are under fire. It was in Downey’s best interest to play a character who was morally upstanding and loyal to his co-workers, but the film also exposed the political interests that would become prevalent within his career. Downey has been far from silent when discussing American politics, and “Good Night, and Good Luck” has aged particularly well in the Trump era.
6. Kiss Kiss Bang Bang (2005)
“Kiss Kiss Bang Bang” was a role made for Downey that both saved his career and promoted legendary screenwriter Shane Black to being a prominent filmmaker. Black had basically invented the “buddy cop” formula with his scripts for “Lethal Weapon” and “The Last Boy Scout,” and “Kiss Kiss Bang Bang” turned the genre on its head. Downey is playing a thief who masquerades as an actor, only to land a part playing a cop, which means he has to go under the wing of a real law enforcement investigator (Val Kilmer) in order to learn the tricks of the trade. It’s meta on multiple levels, acknowledging Downey’s chameleonic acting abilities, ability to reinvent himself, and experiences on the other side of the law.
Black’s snappy, sharp dialogue is a perfect fit for Downey, who offered the perfect context for the film’s satirical edge by offering a fourth-wall-breaking commentary. In addition to relaunching Kilmer as a character actor, “Kiss Kiss Bang Bang” showed that Downey could occupy a charismatic, yet dubious role as a leading man that wasn’t possible for any of his contemporaries. As a way of paying back the favor, Downey insisted to Marvel Studios that Black be hired to direct “Iron Man 3.”
5. Iron Man (2008)
The Marvel Cinematic Universe has faced such a critical decline in the last six years that it’s easy to forget what a genuine breath of fresh air “Iron Man” was. At a time in which the “X-Men” and “Spider-Man” sagas had run their course, Favreau bet on a superhero who built his own luck and took hold of his legacy, defying the wealth and privilege that he was born into.
Casting Downey as a rockstar, billionaire Playboy who transformed into a technical genius wasn’t just a smart way to utilize Downey’s charisma, but a surprisingly effective way to build a compelling character arc. At a time in which superhero films all felt like nothing but escapism, “Iron Man” felt like it was set in a tangible reality, making Tony Stark’s redemptive journey more plausible.
“Iron Man” nailed the tropes of a comic book origin story without feeling antiquated. Tony’s slow process of refining his armor was a case of meticulous worldbuilding, and the romance with Pepper Potts (Gwyneth Paltrow) felt earned. Although the finale of “Iron Man” feels quaint in comparison to the end battles that have topped off every Marvel film since, the stakes are massive because Tony has to risk being a better man.
4. Tropic Thunder (2008)
Released the same year as “Iron Man,” “Tropic Thunder” is such a hilarious, star-studded summer comedy that it’s perhaps not given enough credit for being a brilliant work of satire. Ben Stiller examined the way that movie stars became typecast by amassing a band of pathetic actors who did little more than coast on their personas, and threw them into a real-world crisis because of how little the studios, agents, and financiers of the industry actually cared about them. Giving the most ambitious performance was Downey as Kirk Lazarus, a decorated actor who embarked upon a controversial skin procedure in order to play an African American character.
The notion that “Tropic Thunder” couldn’t be made today is ridiculous. It was obvious at the time that Downey’s performance was lampooning the style of “method acting” that had been touted by intensive performers, and his own experiences in the industry made him perfectly poised to deliver such a scathing portrayal. That Downey could bring such authenticity to a character who is, by his very nature, incapable of actually being genuine, makes for a nuanced approach when Lazarus recognizes the failure of his methods. He’s the scene-stealer in one of the 21st century’s best comedies.
3. Chaplin (1992)
When it comes to Hollywood icons that would seemingly be impossible to replicate, Charlie Chaplin is in the upper tier. Chaplin was not only one of the most influential directors, actors, and comedians in cinematic history, but a figure who stood in for an entire generation of filmmaking that has slowly been erased.
Downey had to embody the Chaplin that audiences around the world had fallen in love with, whilst also showing the dark side of a wounded, embittered man who had been cast out and treated as an outsider. “Chaplin” might seem to have a standard “great man” arc that is similar to other awards-bait biopics, but it’s much thornier as a result of its subject’s complex life.
“Chaplin” does not ignore that the man spent the second half of his life in court cases, both for his sexually devious behavior and for being politically outspoken during a time in which cowardice in Hollywood was plentiful. Downey doesn’t cast judgment on Chaplin as much as he seeks to understand him, and the film manages to capture the entirety of the icon’s life whilst still keeping him at an emotional distance; to imply Chaplin could be “relatable” would simply be untrue.
2. Zodiac (2007)
“Zodiac” is a rare case in which a major filmmaker made what was clearly a masterpiece. It touched on salient issues and worked with A-list talent, only for the film to essentially be ignored upon release. Time has obviously been very kind to David Fincher’s brilliant 2007 serial killer thriller, as it both anticipated the next stage of conspiratorial crime fiction and embodied an era of obsession that perfectly fit within the digital revolution.
What is most surprising about the film’s legacy is that Downey’s performance as the reporter Paul Avery would end up resonating. Despite his vehement dedication to covering important cases, Avery delves into paranoia and addiction when he approaches the truth behind the deadly murders.
Downey doesn’t just beautifully showcase the tragedy of a corrupted genius, but shows how a prickly, outspoken provocateur could be the voice of reason during chaotic times. It sadly didn’t end up getting the awards recognition that it merited, but “Zodiac” did have a silver lining in proving the strength of Downey’s chemistry with Mark Ruffalo, who played Inspector Dave Toschi. The dynamic between Downey and Ruffalo’s Bruce Banner within the next two decades of Marvel films became one of the most endearing, thoughtful, and engaging dynamics within the franchise.
1. Oppenheimer (2023)
An actor rarely wins their Academy Award for what is actually the best performance of their career, and it’s to the credit of Downey’s fame that he was able to get traction for what isn’t a traditionally “baity” awards role. Lewis Strauss is a quiet villain in “Oppenheimer” who is clouded by ambition and personal vendettas, yet lets his lackeys and pawns do most of the hard work to excommunicate J. Robert Oppenheimer (Cillian Murphy). Christopher Nolan’s Best Picture-winning masterpiece is packed with great supporting performances, but it’s through the masterful weaving of the timelines that Strauss emerges as the power hiding in the shadows.
The reveal that it was Strauss’ personal hatred for Oppenheimer that set off a chain reaction of persecution is treated as an operatic twist in the vein of the ones used by Nolan in “Inception” and “Memento,” yet gave Downey the chance to do the type of monologue that any stage actor would dream of. That someone of his fame could so subtly disappear into a role that required him to be deprived of his inherent charisma is an amazing achievement of humility and hard work, solidifying Downey’s fascinating streak of unpredictability.
