There are few stars in Hollywood that have shared a career that’s quite as remarkable as Robert Downey Jr.. He’s played some truly iconic roles, all the while experiencing a wealth of ups and downs.

He burst onto the scene in the 1980s, and like many struggled to cope with the fame, turning to the likes of drugs and drink, developing an alcohol dependence and needing help from rehab in order to get his life, and career, back on track.

That he did, forcing one of the greatest comebacks in cinematic history – worthy of a biopic in itself and he’s never looked back, putting in some incredible performances. But what ranks among his best?

We take a look at five of the greatest movies starring Robert Downey Jr…

1. Iron Man (2008)

It is impossible to discuss Robert Downey Jr.’s career without beginning with Iron Man. Released in 2008, the film transformed Marvel Studios into a cinematic powerhouse and redefined the superhero genre. Downey’s charismatic performance as billionaire inventor Tony Stark perfectly balanced wit, arrogance and vulnerability. His natural charm made Stark instantly likeable, while his emotional journey from self-centred weapons manufacturer to selfless hero gave the film genuine heart.

More than just a blockbuster, Iron Man resurrected Downey’s career and established him as one of Hollywood’s biggest stars. His performance remains one of the defining superhero portrayals of modern cinema.

2. Oppenheimer (2023)

Christopher Nolan’s Oppenheimer reminded audiences that Downey’s talents extend far beyond action films. Playing Lewis Strauss, the influential politician whose rivalry with J. Robert Oppenheimer becomes central to the story, Downey delivered one of the finest performances of his career.

Gone were the fast-talking quips associated with Tony Stark. Instead, he portrayed Strauss with quiet restraint, simmering resentment and calculated ambition. His nuanced performance earned widespread critical acclaim and an Academy Award for Best Supporting Actor, proving that he remains one of the industry’s most accomplished performers.

3. Chaplin (1992)

Long before becoming a global superstar, Downey astonished critics with his portrayal of silent film legend Charlie Chaplin. Capturing Chaplin’s unmistakable physical mannerisms, comic timing and emotional complexity was no easy task, yet Downey delivered a performance of extraordinary depth.

His portrayal earned him his first Academy Award nomination and demonstrated a maturity far beyond his years. Even decades later, Chaplin remains one of the finest biographical performances ever committed to film and showcased the extraordinary range that would define Downey’s career.

4. Zodiac (2007)

David Fincher’s gripping thriller Zodiac is widely regarded as one of the finest crime films of the 21st century. Downey stars as journalist Paul Avery, whose investigation into the infamous Zodiac Killer gradually consumes his life.

Although sharing the screen with Jake Gyllenhaal and Mark Ruffalo, Downey leaves a lasting impression through his razor-sharp dialogue, confidence and gradual emotional decline. Fincher’s meticulous direction and Downey’s layered performance create a fascinating character whose charm slowly gives way to paranoia and despair. It remains one of his most underrated performances.

5. The Singing Detective (2003)

While The Singing Detective received mixed reviews upon release, it deserves recognition as one of the more intriguing entries in Downey’s career. Based on Dennis Potter’s acclaimed television serial, the film follows a hospital patient whose feverish imagination blurs the boundaries between reality and fantasy.

Downey plays Dan Dark, a mystery writer suffering from a debilitating skin condition while wrestling with memories, guilt and vivid hallucinations. It was a particularly significant role, arriving shortly after the actor’s well-publicised personal struggles, and many critics noted the emotional authenticity he brought to the character. His committed performance anchors an often surreal narrative and demonstrates his willingness to embrace unconventional, challenging material.