Our pick of Robert Downey Jr.’s best films, from Zodiac to Iron Man

Robert Downey Jr. in Dolittle  (AP)
Robert Downey Jr. in Dolittle (AP)

Robert Downey Jr. has set the internet on fire by picking out his top films from his career – they’re quite unexpected.

“Honestly, the two most important films I’ve done in the last 25 years are The Shaggy Dog, because that was the film that got Disney saying they would insure me. Then... Dolittle,” Downey Jr. said in a New York Times article published yesterday.

He then explained his reasons behind choosing the 2020 film Dolittle: it took a lot, he said, to turn the film into something remotely “serviceable”; his wife (who was the co-producer of the film) was under a huge amount of pressure; and in the fallout of the “crisis” the husband and wife team – who are founders of the production company Team Downey – changed some of their top advisors.

“And that whole time, my dad was passing away, and as an avoidance mechanism, I decided to send crews over and get his thoughts on his winter years, and that turned into “Sr.”... probably the most important thing I will ever do.”

Released in 2022, “Sr.” is a documentary about Robert Downey Jr.’s dad, filmmaker Robert Downey Sr. An intimate reflection on both Downey Sr.’s life and the relationship between father and son, its sentimental velue is obvious. But, The Shaggy Dog?

Downey Jr. has had a stellar career, acting in a whopping 80 films since his first credited film role in the 1970 comedy Pound. Since then, his credits include major blockbusters, indie favourites and everything in between, including teen science fiction flick Weird Science (1985), the satirical comedy Bowfinger (1999), the 2005 black comedy Kiss Kiss Bang Bang and the indie drama, A Guide to Recognizing Your Saints (2006).

Next up Downey Jr. will star in Christopher Nolan’s Oppenheimer, which opens in cinemas later this month: he plays American businessman Lewis Strauss who was the chairman of the U.S. Atomic Energy Commission.

On the eve of what we assume will be another great performance, here’s our own pick of Downey Jr.’s best films.

Chaplin (1992)

In this biographical comedy from Richard Attenborough, Downey Jr. starred as English comic Charlie Chaplin. The film, which also featured John Thaw, Anthony Hopkins, Milla Jovovich and David Duchovny, told the story of Chaplin’s life. It picked up a handful of awards, including three Oscar nominations (including a Best Actor nomination for Downey Jr.), three Golden Globe Awards nominations, and four British Academy Film Awards (Downey Jr. won Best Actor in a Leading Role).

Critics liked it less, with The New York Times’ 1992 review saying, “Chaplin is to serious biography, even to Mr. Attenborough’s Gandhi, what unfortified cornflakes are to real food. Its slick packaging around what is mostly warm air.” But nearly everyone praised Downey Jr’s performance specifically: The New York Times added that “Mr. Downey and Ms. Chaplin [Chaplin’s own daughter, Geraldine, played his mother Hannah in the film] give the movie what class it has.”

Natural Born Killers (1994)

Oliver Stone’s graphic crime drama saw Downey Jr. playing Wayne Gale, a journliast who is following the case of Mickey Knox (Woody Harrelson) and Wilson Knox (Juliette Lewis), a couple who go on a killing spree. Although the film deals with thorny subjects including childhood trauma, poverty, freedom and the role of the media in the US, it’s somehow utterly exhilarating: with its balance of violence and humour it makes sense that the original story was written by Quentin Tarantino.

Today the film has gained cult status, despite some critics believing it failed to properly develop its more interesting and complicated themes. Tarantino later disowned the film: “I hate that f***ing movie,” he said in 2013. “If you like my stuff, don’t watch that movie.”

Fur: An Imaginary Portrait of Diane Arbus (2006)

A fairly bonkers film, Fur reimagines the life of American photographer Diane Arbus (1923 - 1971) with Nicole Kidman playing Arbus and Downey Jr. playing her lover Lionel Sweeney, a man with hypertrichosis (atypical hair growth). Arbus was known for her boundry-pushing images, which is where screenplay writer Erin Cressida Wilson and director Steven Shainberg (both of whom made the 2002 American erotic comedy Secretary) must have found some of their inspiration. The film is zany, to say the least, but incredibly captivating.

“One of the weirdest yet amazing movies of our lifetime,” said a fan on the trailer. “That’s exactly what I expect from Nicole Kidman and R. Downey Jr. Great movie. It makes you think about it even when the lights go out,” said another.

Zodiac (2007)

David Fincher’s adaptation of Robert Graysmith’s true crime novel, Zodiac, is seriously terrifying. Jake Gyllenhaal played Graysmith, a political cartoonist working for the San Francisco Chronicle who ended up becoming obsessed with a series of unsolved murders around the city in the late Sixties and early Seventies. Downey Jr. played reporter Paul Avery. The story follows the duo as they work together to try and work out the identity of the killer.

“Rarely has a film with so much blood on its hands seemed so insistently alive,” said The New York Times, which described the film as “magnificently obsessive”, “informed by history and steeped in pulp fiction,” adding that “the storytelling is seamless”.

Iron Man (2008)

Although Downey Jr. was already extremely established in Hollywood, Iron Man is seen as being the film that revived his career. The actor had struggled with drug addiction for years. By 2008 he was on the mend, but arrests and stints in rehab had had a huge impact on his career.

Everything changed when director Jon Favreau saw him as a good fit to play maverick inventor turned superhero Tony Stark in Iron Man, backing the actor despite some alleged real reluctance from Marvel. Favreau’s gamble paid off: the film was a huge hit, making $585.3 million worldwide at the Box Office. Downey Jr. was launched into superstardom: he has since starred in nine subsequent Marvel films, including The Incredible Hulk (2008), The Avengers (2012) and Spider-Man: Homecoming (2017).

Sherlock Holmes (2009)

Sherlock Holmes is a character that lives so large in people’s imaginations that it can be a struggle to represent him on screen. There was actor Jeremy Brett, who came close perfectly bringing the character to life in the late Eighties Granada TV series Sherlock Holmes. But until Downey Jr. took over the role, the character had never truly been successfully recreated on film. Guy Richie’s 2009 adaptation energised the Victorian novel, adding his signature action sequences, and a huge amount of humour, to the role – which worked brilliantly with Downey Jr. playing Holmes and with Jude Law playing Dr. John Watson.

“Sr.” (2022)

“Sr.” explores the life of anti-establishment filmmaker Downey Sr. who died from Parkinson’s in 2021. It focuses on the relationship between the maverick filmmaker – who in the documentary is making his own documentary about his life – and his Marvel Universe-starring son.

Speaking about the experience of making the film, director Chris Smith said: “Larger than life, but open and human as ever, it was such a pleasure and life-affirming experience to capture some glimpses of the highs, lows, and everything in between.”

Oppenheimer is set to open in cinemas on July 21