Once upon a time, Robert Downey Jr. was an actor starring in movies not tied into the Marvel Universe. True, his Tony Stark kickstarted the MCU and remains one of its most indelible characters, but beyond the Iron suit (or maybe alongside it), RDJ explored some challenging, small films, and branched out into more serious and comedic fare. He was a daring young actor, a troubled middle-aged actor, and eventually one of the biggest stars in all the land.

Here are his ten finest roles, and they come in all shapes and sizes:

10. Tommy Larson, Home for The Holidays – Jodie Foster’s Thanksgiving family comedy taps into a holiday rarely exploited on screen for its stressful and unnerving comedic potential. Downey plays the gay brother of Holly Hunter’s, Claudia, and they absolutely sell their relationship. Downey is the troublemaker here, a perfect fit for the mischievous persona he built early in his career.

9. Wayne Gale, Natural Born Killers – Downey took a bit part in Oliver Stone’s searing pop culture expose and transformed it into one of the most memorable parts of a fascinating film. Part Robin Leach, part Geraldo, part any number of other salacious TV personalities, Wayne Gale is a schlock salesman ready to exploit the sensational murder spree of Mickey and Mallory Knox.

8. Julian, Less Than Zero – Revisiting Less Than Zero these days, after we know the trials of Robert Downey Jr’s personal life, his portrayal of Bret Easton Ellis’s troubled LA youth is even more unsettling than it was in 1987. Julian is adrift in a world of morally bankrupt LA teens, and finds himself spiraling out of control. Crippled by drugs and selling his body, a young RDJ shows off his raw acting power like few other actors of his age at the time (he was only 22) could have done.

7. Harry Lockhart, Kiss Kiss, Bang Bang – Shane Black’s neo noir comedy has gathered a cult following over the years, thanks in part to his stunning ability to get good work out of Val Kilmer many years after he’d burned too many bridges to count in Hollywood. But without the rapid-fire charm of Downey’s wannabe big time crook, Harry, the film wouldn’t sing the way it does.

6. Terry Crabtree, Wonder Boys – Curtin Hansen’s adaptation of Michael Chabon’s terrific novel is an intimate, sometimes overlooked gem of a picture. Michael Douglas deserved an Oscar nomination for his role as a disheveled writer and professor, but Robert Downey Jr. brought an air of misplaced confidence and arrogance to the film as “Crabs,” his deviously gay editor. Douglas and Downey sell their authentic friendship on screen, and Crabtree’s Eddie Haskell-like meddling is responsible for most of the hilarious moments throughout the picture.

5. Tony Stark/Iron Man, The MCU – Where would the Marvel Cinematic Universe be without Robert Downey Jr.? Of all the casting decisions Marvel has made over the years, RDJ and Tony Stark seem to exist as one. It’s almost as if the character was created in the 60s with some sort of prophetic insight into the future. Stark and Iron Man capture all the bravado and wit that defines Downey as a man and an actor.

4. Blake, Two Girls and A Guy – In the middle of some of his toughest times as a human being, in the throes of dangerous drug addiction, Downey was managing to find his way into incredibly small but fascinating work. In Two Girls and A Guy, Downey’s Blake finds himself in a sticky situation when his two girlfriends find out about one another and decide to confront him in his apartment. This is Downey doing what he does best, using his smarmy wit to create a character we detest but somehow manage to truly enjoy being around at the same time.

3. Kirk Lazarus, Tropic Thunder – In a perfect sendup of method acting, Robert Downey Jr. played the insanely dedicated thespian Lazarus in Ben Stiller’s pitch perfect comedy. Lazarus is such a method actor, he dyes his skin in order to accurately portray an African-American soldier in Vietnam. Rife with racial barbs and a commentary of “serious” acting, this would be Downey’s second Oscar nomination, an impressive feat since this was a harebrained comedy top to bottom.

2. Charlie Chaplin, Chaplin – Downey’s performance as Chaplin was set up to be the first of many Oscar nominations, and probably a handful of wins, for the actor. Only his personal life began upending his work. Nevertheless, Downey embodies the legend with a balance of darkness and light. Despite the fact Richard Attenborough’s film around Downey’s performance was lacking, Downey shined through.

1. Paul Avery, Zodiac – David Fincher’s Zodiac is a film less about the killer himself, and more about the lives the murders affected (beyond the victims and families of course) as they pursued the truth. Jake Gyllenhaal’s obsessed cartoonist may be the lead, and Mark Ruffalo’s desperate detective may have more screen time, but Robert Downey Jr.’s eccentric, drug-addled, alcoholic journalist Paul Avery quietly dominates. The last time we see Avery in the film, crippled by booze and sitting in a darkened boat house watching Pong on his TV, is one of the more unforgettable falls of a human being in all of cinema.