With his quick and silver tongue and boyish charm, Hollywood stalwart Robert Downey Jr. has made a career in film out of knowing just what to say and when to say it. Going all the way back to the mid-80s when he starred in films like Weird Science, Back to School, and even a season on Saturday Night Live, it was Downey who had the perfect timing to deliver a witty barb. Since then, his career has evolved into more dramatic roles, but there’s always a hint of that jokester with the winsome smile that underscores most of the actor’s performances. He made one of the most colossal comebacks in recent memory when he landed the part of Tony Stark in the Iron Man films and subsequent MCU Avengers sequels. From a fringe member of the ‘brat pack’ to bell cow of the Marvel Cinematic Universe, here is a list of his best performances.
Tony Stark in the ‘Iron Man’ Franchise
Did Downey get a second lease on life after he deftly played Stan Lee’s industrialist/superhero Tony Stark in the movie that essentially rebooted the entire era of the big-budget Avengers films, or what? Downey’s strengths play right into what audiences wanted to see from Stark with his dry sense of humor and intelligence. The original Iron Man (2008) did a whopping $585 million at the box office. After the sequel was deemed good but not great, Downey hit pay dirt again with Iron Man 3 which cleared an astonishing $1.2 billion. The overwhelming success of Downey in the three films really served to anchor the explosion of MCU movies that have hit theaters over the past 15 years.
Julian Wells in ‘Less Than Zero’ (1987)
Less than Zero is really Downey’s announcement as an actor to be taken seriously. He had done well in a handful of films in the 80s like The Pick-Up Artist and had some other supporting roles, but in the film based on the novel of the same name by Bret Easton, his turn as the drug-addled black sheep of a well-to-do California family is the role that you can point to as the moment Downey proves that he is capable of playing heavy and supremely flawed characters. His portrayal of Julian Wells is without a doubt the springboard that would lead to a series of more dramatic roles that would come later in his career.
Charlie Chaplin in ‘Chaplin’ (1992)
Tackling the iconic silent film star in the biopic Chaplin garnered Downey his first of two Academy Award nominations. The true story of the mustached star who took on the persona of “The Tramp” during the early film era of the 1920s through the 1940s was a spot-on portrayal and the Academy took notice with a nod for Best Actor. Downey perfectly embodies the first true “movie star” who starred in films like The Kid, A Woman in Paris, and later in Modern Times and The Great Dictator. From his trademark penguin waddle to his slapstick physicality, Downey owns the role while establishing himself as one of the best actors in Hollywood.
Wayne Gale in ‘Natural Born Killers’ (1994)
Downey is the intrepid shock journalist, Wayne Gale, in the 1992 Oliver Stone thriller about two young lovers who go on a bloody killing spree in Natural Born Killers. Wayne Gale is supposed to be a Geraldo Rivera type, no-holds-barred interviewer as he will do anything and everything in his power to get the scoop on the latest murders by trouble youths, Mickey and Mallory (Woody Harrelson and Juliette Lewis). This role required Downey to revert back to some of the goofiness and schlocky on-air antics that he can so deftly tap into whenever a character calls for it. It wasn’t a main role, but Downey left an indelible signature on the film.
Terry Crabtree in ‘Wonder Boys’ (2000)
The part of Terry Crabtree in the Curtis Hanson-directed Wonder Boys gave us all the things that we love about Downey as an actor. As creative writing professor Grady Tripp’s (Michael Douglas) editor, Crabtree is a sarcastic, deadpan wannabe writer who is both a friend to Tripp and a thorn in his side, constantly trying to give the flustered academic some inspiration to continue writing a second fiction novel. Downey is right at home in the world of Academia as his ability to deliver lines with pithiness and dry humor is when he is at his best. The film was well-received but is still considered underrated, as is Downey’s performance as Crabtree.
Harry Lockhart in ‘Kiss Kiss Bang Bang’ (2005)
Image via Warner Bros.
Proving once again that he can take on a role in any genre of film, the actor stepped into the part of Harry Lockhart in the criminally underrated neo-noir dark comedy thriller, Kiss Kiss Bang Bang, directed by Shane Black in his directorial debut. Lockhart is a petty criminal/struggling actor who suddenly finds himself in Hollywood for a screen test in this fun and twisty suspense piece that also stars Val Kilmer and Michelle Monaghan. Downey is excellent as Lockhart, a man out of his depth when he becomes embroiled in a mysterious murder that takes him into some of the seediest parts of Tinseltown. The character is another combination of whimsy and confusion who is trying to survive his short trip that has been turned completely upside down.
Paul Avery in ‘Zodiac’ (2007)
Three parts drama and two parts dry wit is the best way to describe Paul Avery, a boozy crime reporter for The San Francisco Chronicle during the era of the Zodiac Killer. Master director David Fincher captures Avery as a washed-out, jaded journalist whose passion for the job has waned during the failed attempt to discover the serial killer’s true identity in 2007’s Zodiac. Downey is part of a stellar ensemble that includes Jake Gyllenhaal, Mark Ruffalo, and Anthony Edwards – all of whom are trying to stop the menace of Northern California in the late 80s and 70s. As Avery, Downey reprises some of Julian Wells in Less than Zero with Terry Crabtree from Wonder Boys to deliver a compelling character in a grim and gritty thriller.
Sherlock Holmes in ‘Sherlock Holmes’ (2009)
With a penchant for bringing eccentric intelligence to most of his characters, Downey is the perfect choice to play the most famous detective of all time in the Guy Ritchie fueled-up take on Sir Arthur Conan Doyle‘s stories. This part feels as if it were written with Downey in mind as it is a combination of everything that makes Downey so appealing on screen. He brings the quirkiness, the humor, and the oddball mannerisms mixed with an unmatched acumen for observational humor to the classic character. No one could have been Ritchie’s Holmes the way Downey is. One of his best performances and very much worthy of its sequel two tears later in Sherlock Holmes: A Game of Shadows.
Robert Merivel in ‘Restoration’ (1995)
Restoration is a notable entry on this list as it marks Downey’s only real foray into the old English period pieces that dominated Hollywood in the 90s. The part is just what the doctor ordered in that it requires Downey’s young medical student Robert Merivel to engage in a series of debaucheries and behavior unsuitable for an associate of King Charles II and the royal family. It’s a safe bet that Merivel is what Downey would have been had he existed in 17th-century England, and plays the character from Rose Tremain‘s 1989 novel with aplomb and solidified his place as one of Hollywood’s most versatile actors.
