Ten years after he first donned Iron Man’s suit of armor, Robert Downey Jr. has reprised his role as the billionaire superhero in the Marvel epic “Avengers: Infinity War.” The film finds the universe’s greatest heroes teaming up to stop the deadly Thanos (Josh Brolin) from gathering the infinity stones with the intention of wiping out half of the universe’s population. Downey Jr. first played the role in 2008’s “Iron Man,” and has appeared in eight subsequent Marvel movies. Of course, his career hasn’t been limited to the Marvel Cinematic Universe. So in honor of his latest big screen achievement, let’s take a look back on some of his best performances. Tour through our photo gallery above of Downey Jr.’s 20 greatest films, ranked from worst to best.
The son of underground filmmaker Robert Downey Sr. and actress Elsie Downey, Robert Downey Jr. made his acting debut at age five in his father’s film “Pound” (1970). He received his first Oscar nomination in 1992: Best Actor for his performance as silent movie legend Charles Chaplin in “Chaplin.” It took 16 years for him to return to the Oscar race: Best Supporting Actor for his role as an Australian actor who surgically alters himself to play an African-American platoon leader in “Tropic Thunder” (2008).
Both films also brought him Golden Globe nominations. In addition, the Hollywood Foreign Press Association rewarded Downey Jr. with three prizes: Best Ensemble for “Short Cuts” (1993), Best TV Supporting Actor for “Ally McBeal” in 2001, and Best Comedy/Musical Actor for “Sherlock Holmes” (2009). His role on “Ally McBeal” also brought him a SAG Award win as well as an Emmy bid as Best Comedy Supporting Actor.
Take a look through our photo gallery of Downey, Jr.’s greatest films, including a few for which he was egregiously snubbed at the Oscars.
20. ‘Chances Are’ (1989)
Emilio Ardolino’s “Chances Are” is one of those high-concept romantic comedies that could easily spin out of control: a dead D.A. is re-incarnated as an aspiring reporter (Downey, Jr.) and unwittingly falls in love with his daughter (Mary Stuart Masterson) from his previous life. When he finds out, he tries to end the relationship and resume a romance with his widow (Cybill Shepherd), who ignores the frustrated advances of her best friend (Ryan O’Neal). Luckily, “Chances Are” is smart, funny, and charming, making for an old-fashioned, light-hearted entertainment.
19. ‘Home for the Holidays’ (1995)
For anyone who’s ever dreaded spending Thanksgiving with their family, Jodie Foster’s “Home for the Holidays” will send a chill down your spine and a chuckle in your belly. Holly Hunter stars as Claudia Larson, a woman who faces the dreadful prospect of returning home for Thanksgiving after losing her job. Downey, Jr. costars as Tommy, Claudia’s gay brother who spars with his brother-in-law (Steve Guttenberg). The film avoids turning Tommy into a one-dimensional stereotype, instead creating a fully-rounded character who’s about more than just his sexuality. In fact, “Home for the Holidays” competed at the GLAAD Media Awards as Best Film.
18. ‘The Singing Detective’ (2003)
Downey, Jr. shows off his singing and dancing chops in Keith Gordon’s big screen adaptation of Dennis Potter’s BBC series. He plays Dan Dark, a writer confined to a hospital bed due to a painful skin condition. With his body failing, he lets his mind loose and imagines a mashup of film noir and Technicolor musical spectaculars. Though the two-hour film can’t capture every nuance of Potter’s original eight-hour epic, Downey makes for a charming and empathetic private eye, and the musical sequences are dazzling.
17. ‘Restoration’ (1995)
In Michael Hoffman’s “Restoration,” Downey, Jr. dons a frilly wig and puffy shirt to play Robert Merivel, a 17th century medical student. Merivel enjoys a life of debauchery after saving the life of King Charles II’s (Sam Neill) favorite spaniel, only to be cast out after falling in love with one of the King’s favorite mistresses (Polly Walker). Meanwhile, the Black Plague and the Great Fire devastate London. Eugenio Zanetti’s production design and James Acheson’s costumes lavishly recreate the decadence of the royal court and the destitution of the London streets, and both won well deserved Oscars.
16. ‘Soapdish’ (1991)
“Soapdish” did for soap operas what “Network” did for nightly news, only a tad more farcically. Directed by Michael Hoffman, the film combines the on-screen and off-screen drama of a daytime soap. Downey, Jr. plays David Seton Barnes, a young producer who conspires with an ambitious blonde bombshell (Cathy Moriarty) to get her a bigger role by writing off the show’s biggest star (Sally Field). Complications arise, with absurdly hilarious results. Kevin Kline received a Golden Globe nomination as Best Comedy/Musical Actor for playing one of the soap’s former stars who returns after his character is beheaded.
15. ‘A Scanner Darkly’ (2006)
As a performer, Downey, Jr. is known to be animated, so Richard Linklater’s “A Scanner Darkly” is a perfect fit for him. Based on the novel by Philip K. Dick, the film imagines a future in which a mind-altering drug named Substance D has swept the nation. Police detective Bob Arctor (Keanu Reeves) is part of a secret network of high-tech surveillance and undercover informants who’s tasked with infiltrating the drug’s underworld, becoming addicted to Substance D in the process. Downey, Jr. costars as James Barris, one of Arctor’s drug-addicted housemates. Linklater shot the film digitally then animated over the cells with interpolated rotoscope, making for a very trippy visual experience.
14. ‘Richard III’ (1995)
Among the Shakespeare-adapted-to-modern-day movies, Richard Loncraine’s “Richard III” is one of the best. Loncraine resets the play in 1930s London, imagining an alternative history in which fascism has swept the country. Ian McKellen gives one of his best performances as the evil hunchback who murders his way into becoming King. Downey, Jr. costars as Lord Rivers, one of Richard III’s many victims. The film received Oscar nominations for its Art Direction and Costumes, yet all of the actors were inexplicably snubbed (McKellen did compete at the Globes and BAFTA).
13. ‘Good Night, and Good Luck’ (2005)
Although it takes place over 60 years ago, it’s hard not to draw parallels between the events portrayed in George Clooney’s “Good Night, and Good Luck” and what’s going on today. The film recounts the battle between CBS newscaster Edward R. Murrow (David Strathairn) and Senator Joe McCarthy, who used his power to hunt down Communists in the U.S., caring little for whether or not they actually belonged to the vilified party. Downey, Jr. plays Joseph Wershba, a CBS reporter who’s secretly married to a co-worker (Patricia Clarkson). Now more than ever, “Good Night, and Good Luck” is a testimony to the importance of a free press in the face of government deception. Downey, Jr. was nominated at SAG for Best Ensemble, and the film competed for six Oscars including Best Picture.
12. ‘Kiss Kiss, Bang Bang’ (2005)
Shane Black‘s “Kiss Kiss, Bang Bang” is one of those movies that keeps twisting and turning inside of itself until it becomes as much about its construction as it is about its plot. Downey, Jr. plays Harry Lockhart, a wannabe actor who moves from New York to Los Angeles and starts taking private eye lessons from a gay detective (Val Kilmer) named Gay Perry. While at a party he encounters an old flame (Michelle Monaghan), and from there ensues a plot so complex it would leave Raymond Chandler scratching his head (the film, in fact, references Chandler’s works in five chapter headings). “Kiss Kiss, Bang Bang” is sly, sleek, self-referential entertainment that’ll keep fans returning to unlock its many mysteries.
11. ‘Less Than Zero’ (1987)
Downey, Jr. became a star in this harrowing adaptation of Brett Easton Ellis’ bestseller. Directed by Marek Kanievska, the film centers on three rich best friends (Downey, Jr., Andrew McCarthy, Jami Gertz) who go their own ways after graduating from high school in Beverly Hills. Clay (McCarthy) returns home from college to find his ex-girlfriend (Gertz) shacking up with his old pal Julian (Downey, Jr.), who is spiraling out of control from drug use. “Less Than Zero” doesn’t lecture, but instead presents the harsh realities of drug addiction and the terrible toll it takes not just on the user, but on their loved ones.
10. ‘Bowfinger’ (1999)
Downey, Jr. gives a brief but memorable performance in Frank Oz’s hilarious Hollywood satire. Steve Martin wrote the script and plays Bobby Bowfinger, a wannabe filmmaker who will stop it nothing to get a B-grade sci-fi flick produced with the world’s biggest star (Eddie Murphy), even if it means shooting the movie without the star knowing it. Downey, Jr. plays Jerry Renfro, a powerful studio executive who Bowfinger pitches the script to. What makes “Bowfinger” special is the affection it shows to its cast of La La Land dreamers. The film is neither mean-spirited nor cruel, but is instead a gentle and loving ode to the passion that drives even the most untalented of people. Oh, and it’s very, very funny.
9. ‘The Avengers’ (2012)
The gang’s all here for Joss Whedon’s “The Avengers,” the first of the superhero mashup movies that solidified the Marvel Cinematic Universe as being true to its title. Downey, Jr. reprises his role as billionaire Tony Stark (a.k.a Iron Man), who teams up with Captain America (Chris Evans), the Hulk (Mark Ruffalo), Thor (Chris Hemsworth), Black Widow (Scarlett Johansson), and Hawkeye (Jeremy Renner) to stop Thor’s evil brother Loki (Tom Hiddleston) and his alien army from enslaving Earth. Though these heroes often go their separate ways, they’ve had to team up again and again to save the world from destruction, including in “Avengers: Age of Ultron” and “Avengers: Infinity War.”
8. ‘Short Cuts’ (1993)
Downey, Jr. is just one of twenty-two protagonists in this intimate epic from Robert Altman. Based on the writings of short story author Raymond Carver, the film examines the lives of several Los Angeles residents struggling with work, love, and death. Downey, Jr. plays Bill Bush, a makeup artist who plays house in his neighbor’s apartment with his wife (Lili Taylor). As the lives of this disparate group intertwine in unexpected, hilarious, and at times tragic ways, Altman deftly highlights the random nature of existence. Surprisingly, not one member of the cast was recognized at the Oscars, despite winning a special award at the Golden Globes for Best Ensemble. Altman did contend for Best Director (the film’s sole bid), but lost to Steven Spielberg (“Schindler’s List”).
7. ‘Natural Born Killers’ (1994)
When it was released in 1994, Oliver Stone’s “Natural Born Killers” caused quite a stir. Loosely based on an original screenplay by Quentin Tarantino, the film follows Mickey (Woody Harrelson) and Mallory Knox (Juliette Lewis), two deeply damaged people who fall in love and paint the country red in a nationwide killing spree. Their case catches the eye of the media, including a sleazy tabloid host (Downey, Jr.) who interviews Mickey while he’s imprisoned, keeping the camera rolling even when a riot ensues. Shot in Stone’s characteristic jagged filmmaking style and featuring extreme, almost cartoonish violence, “Natural Born Killers” isn’t for everybody. Still, the film remains a powerful indictment of our fascination with bloodshed, especially in this age of mass shootings.
6. ‘Wonder Boys’ (2000)
Curtis Hanson’s “Wonder Boys” captures the rhythms of campus life as well as any film possibly could. Michael Douglas gives one of his best performances as Grady Tripp, a constantly stoned English professor dealing with problems from his students (Tobey Maguire and Katie Holmes), his mistress (Frances McDormand), and his publisher (Downey, Jr.), who’s been waiting on his elusive second novel for seven years. “Wonder Boys” is more honest and authentic than movies like “Back to School,” but no less whacky. Bob Dylan won an Oscar for his original song “Things Have Changed,” and the film competed for Best Adapted Screenplay (Steve Kloves) and Best Film Editing.
5. ‘Sherlock Holmes’ (2009)
Downey, Jr.’s franchise entertainment isn’t limited to the MCU. In Guy Ritchie’s “Sherlock Holmes,” he brings Arthur Conan Doyle’s iconic sleuth to the big screen for a new generation of moviegoers. Suffice it to say, this isn’t your father’s Sherlock Holmes: this guy uses his body as much as his brain to solve mysteries (still, he is quite brilliant). The plot involves Holmes and his sidekick, Dr. Watson (Jude Law), trying to stop the evil Lord Blackwood (Mark Strong) from taking over London. The film is a marvel of dazzling special effects and hyper-kinetic action. Downey, Jr. won the Golden Globe as Best Comedy/Musical Actor, and reprised the role in the 2011 sequel “Sherlock Holmes: A Game of Shadows.”
4. ‘Iron Man’ (2008)10 years ago, Marvel Studios kicked off its plot for domination of the world’s movie market with “Iron Man,” and what a
kickoff it was. Downey, Jr. stars as Tony Stark, a fast-talking, narcissistic billionaire engineer who develops a weaponized suit of armor after he’s held captive in an Afghan cave. After he escapes, he turns his attentions to forces of evil back home. Director Jon Favreau keeps things light, witty, and entertaining, allowing his star’s personality to shine through that armor mask. The film spawned countless superhero flicks and two direct sequels – “Iron Man 2” (2010) and “Iron Man 3” (2013) – but the first remains one of the very best superhero films, due in large part to Downey, Jr.’s charisma and charm.
3. ‘Zodiac’ (2007)
David Fincher’s “Zodiac” is one of those rare movies that’s about two different things at once, and is skillful at both. On the one hand, it’s a newspaper drama about a cartoonist (Jake Gyllenhaal) and a reporter (Downey, Jr.) who become obsessed with the Zodiac Killer, an unidentified individual who terrified Northern California with a killing spree in the late 1960s/early 1970s. On the other hand, it’s a police procedural about two San Francisco detectives (Mark Ruffalo and Anthony Edwards) tracking the killer down. Both stories coexist in perfect harmony with each other, making for a terrifying and riveting examination of one of the most perplexing unsolved mysteries in recent history. Downey, Jr. gives one of his best performances as Paul Avery, whose life unravels when he becomes a target of the Zodiac. Stunningly, “Zodiac” didn’t receive a single Oscar nomination. Now that’s criminal.
2. ‘Tropic Thunder’ (2008)
There is perhaps no riskier role in the history of motion pictures than that of Kirk Lazarus (Downey, Jr.) in “Tropic Thunder.” Directed by Ben Stiller, the film centers on a group of narcissistic actors – action star Tugg Speedman (Stiller), 5-time Oscar-winner Lazarus, and crass comedian Jeff Portnoy (Jack Black) – who become lost in the jungle while filming an overblown Vietnam war epic. Lazarus, a blonde-haired, blue-eyed Australian, surgically darkens his skin to play the film’s African American platoon leader. A method actor in the extreme, Lazarus remains in character at all times, often believing he is in fact a black man. It’s the kind of performance that could easily be cringe-inducing, but in Downey, Jr.’s skillful hands, Lazarus becomes a send up of racial stereotypes and movie star egotism. He received an Oscar nomination as Best Supporting Actor, losing to Heath Ledger (“The Dark Knight”).
1. ‘Chaplin’ (1992)
Downey, Jr. is eerily uncanny as silent movie legend Charles Chaplin in Richard Attenborough’s autobiographical drama. Not only does he look strikingly like the director and star of “The Gold Rush,” “City Lights,” “Modern Times,” and “The Great Dictator” (to name but a few), but he manages to capture the blithe spirit and cunning charm that made Chaplin the world’s biggest star. It also delves into the great well of sadness that drove his genius, from his mentally-ill mother (Geraldine Chaplin, playing her own grandmother) to his vagabond upbringing in music halls to his failed romances with too-young women. Downey, Jr. won the BAFTA as Best Actor and received an Oscar nomination, losing to Al Pacino (“Scent of a Woman”).