Robert Downey Jr.— pardon me, Academy Award winner Robert Downey Jr. — has been acting for over 40 years. The actor rose to prominence in the 1980s before achieving international stardom in the new millennium with his portrayal of Tony Stark, aka Iron Man, in the Marvel Cinematic Universe.

Although his career has seen numerous peaks and valleys, Downey Jr. has proven himself a man of impressive resilience; whenever he’s seemingly been discarded, he always finds his way back to the top. Downey Jr. will next be seen in a new HBO television show, Park Chan-wook’s The Sympathizer, which is further proof that he is indeed in the prime of his career. And while he has starred in many memorable pictures, these select few are the best by far.

7. Chaplin (1992)

Downey’s first major critical hit came in 1992, and was guided by the confident hand of the late great Sir Richard Attenborough. Chaplin paints a loving portrayal of the star’s life, chronicling his childhood, his early success in vaudeville, his eventual stardom in silent pictures, and his later triumphs, which culminated with his receiving of the 1972 Honorary Academy Award.

Chaplin earned Downey Jr. his first Oscar nomination and won him a BAFTA Award. It’s easy to see why. It’s the type of performance Hollywood loves, as it honored one of its greatest performers with great care and love. However, it’s also quite by the numbers, avoiding any sort of stance on Chaplin beyond absolute respect. The film’s one major asset is Downey Jr., who delivers a career-defining performance as the acting genius. The actor nails Chaplin’s mannerisms to a tee, crafting a remarkably accurate portrayal that is both impressive and somewhat eerie.

6. Tropic Thunder (2008)

Downey Jr. stars opposite Ben Stiller and Jack Black in Stiller’s 2008 satirical war comedy Tropic Thunder. The film follows three conceited actors filming a war movie, with each trying to prove themselves to their detractors. Unbeknownst to them, the film’s director has placed them in the middle of the jungle, where they’ll come into contact with an actual dangerous conflict that will test their skills — and, as it turns out, their actual acting talent.

Irreverent, politically incorrect, and bitingly hilarious, Tropic Thunder is among the 21st century’s best satires, a war movie unlike any other. Downey Jr. received his second Oscar nomination for playing prima donna method actor Kirk Lazarus, who goes to extreme lengths to bring his characters to life. Lampooning the many method actors who get so into their roles that they lose their grip on reality, Downey Jr. delivers one of the great comedic performances of the 2010s. Tropic Thunder‘s unapologetic humor will not be for everyone, but those who enjoy a good dose of edgy comedy will surely laugh out loud.

Tropic Thunder is available to stream on Peacock.

5. Kiss Kiss Bang Bang (2005)

The crime comedy Kiss Kiss Bang Bang, Shane Black’s directorial debut, is among Downey Jr.’s most underappreciated efforts. The actor stars as Harry Lockhart, a clueless criminal who gets mistaken for an actor and sent to Los Angeles to train with a real-life PI in preparation for a role. When they get involved in a real crime, the duo will need to rely on their wits to come out on top.

Kiss Kiss Bang Bang sees Downey Jr. at his most ridiculous, with the actor willing to act like a buffoon for our entertainment. His chemistry with Val Kilmer is incredible, as is his delivery of Black’s witty, absurdist dialogue. With this film, Black crafts both a satire of and a love letter to the noir genre and he blends classic themes with delightfully silly comedy, with the result being a unique and endlessly entertaining movie that invites multiple rewatches.

Kiss Kiss Bang Bang is available to rent or purchase on Amazon and other digital vendors.

4. Iron Man (2008)

The late 1990s and early 2000s were a difficult time for Downey Jr.’s career, to the point where many considered his best days to be behind him. However, like a Hollywood fairy tale, Downey Jr. rose from the ashes thanks to Jon Favreau’s 2008 superhero hit Iron Man. Based on the eponymous Marvel character, the film sees playboy Tony Stark become the superhero Iron Man after a life-changing experience as a hostage of a terrorist organization.

It’s truly impossible to overstate Iron Man‘s importance, not only for Downey Jr.’s career, but to the entertainment industry in general. The film earned critical acclaim and was commercially successful, laying the basis for the Marvel Cinematic Universe and starting the 21st century’s defining franchise — so far, anyway. It also revived Downey Jr.’s career, reminding everyone of his considerable charm and talent and relaunching him as an A-lister. The role of Iron Man would become synonymous with him, cementing his legacy as a bona fide screen titan.

Iron Man is available to stream on Disney+.

3. Avengers: Endgame (2019)

Downey Jr.’s journey as Iron Man ended 11 years after his debut with the once-in-a-generation cinematic triumph that was Avengers: Endgame. A culmination of 10 years of continuous storytelling, Endgame follows the remaining Avengers as they plan an ambitious time heist to undo the damage done by Thanos in Avengers: Infinity War.

Larger than life and narratively satisfying, Avengers: Endgame was the cinematic event of the 2010s. Downey Jr.’s Tony Stark gets the film’s best arc, as the character sacrifices himself to save the world. It’s a beautiful journey that started in Iron Man and which Downey Jr. and MCU overlord Kevin Feige took great care in presenting.

Iron Man’s noble death is among the most powerful moments in modern pop culture, feeling earned yet devastating. And while there’s talk that Downey Jr. will return to the MCU, hopefully, he won’t. He left the now-struggling franchise at just the right time, and as a certified icon, no less — why ruin that?

Avengers: Endgame is available to stream on Disney+.

2. Zodiac (2007)

Leave it to David Fincher to direct what is possibly the best and most disturbing thriller of the noughties. Starring Jake Gyllenhaal, Mark Ruffalo, and Downey Jr., Zodiac follows the manhunt for the notorious Zodiac Killer, who terrorized the San Francisco Bay Area during the 1960s and early ’70s.

Taut, unnerving, and outright unforgettable, Zodiac is among the best crime movies ever and worthy of the word “masterpiece.” Confidently guided by Fincher’s firm hand, the film presents an urgent and anxiety-inducing narrative further enhanced by a trio of amazing performances. Zodiac understands the power of subtlety and suggestion; like the infamous serial killer it dramatizes, the film taunts its audience with the promise of answers. Yet, Zodiac isn’t interested in providing them, leaving a chilling and relentless sensation in its unsuspecting audience.

Zodiac is available to stream on PlutoTV.

1. Oppenheimer (2023)

Downey Jr. delivers the performance of his career under Christopher Nolan’s direction. The biographical thriller Oppenheimer stars Cillian Murphy as the titular scientist and chronicles his creation of the atomic bomb and his severe guilt over his legacy’s devastating nature.

Winning seven Academy Awards and grossing nearly $1 billion at the box office, Oppenheimer is a cinematic triumph of staggering proportions. The film does the impossible, turning a talky story about physics into a riveting examination of the nature of legacy and the horrors of war. Downey Jr. is brilliant as Lewis Strauss, the story’s antagonist, walking a fine line between petty insecurity and barely disguised contempt. It’s a tough role to pull off, but Downey makes it seem effortless, creating a memorable villain that will surely rank among the best of the decade.