In one of his first performances, Robert has an uncredited role in his father’s film Greaser’s Palace, a spaghetti western take on the story of Christ. Robert Downey Sr., was an accomplished independent filmmaker creating some notorious in-your-face comedies. Sure, it was a bit part, but his dad was smart enough to recognize his kid's talent early on.

I’m sure we all remember Gary and Wyatt wearing bras on their heads, trying to make Kelly LeBrock come to life. Besides the film bristling with sixteen-year-old hormones, Weird Science is arguably where Robert Downey, Jr. got his acting chops. Playing antagonist to Gary and Wyatt’s boner-driven fantasy, Jr. doesn’t get too much screen time, but it’s one of the first times we can see him in a film worth watching. Now a eighties classic, Weird Science has become synonymous with John Hughes's growing legend of angst-ridden teenage films.

Is anyone not in this movie? Anthony Hopkins, Dan Aykroyd, Diane Lane, Marisa Tomei … Richard Attenborough’s second biopic has Downey front and center playing the iconoclastic comic in an Oscar-nominated performance. This is the first film on the list that really shows Downey’s full range, as he had to recreate Chaplin's amazing ability to make us laugh and cry. Most impressive is Downey’s physicality, which is mesmerizing particularly in the sequences where he is recreating some classic Chaplin cinema moments. Although Downey lost the Oscar to Al Pacino, his performance is still a delight and allows us to gain some insight into someone who changed the world through cinema.

I really don’t like this film, but that doesn’t mean I can’t appreciate it. This is the kind of movie that you only have to see once, because it haunts you the rest of your life. Following a psychopathic couple that kills fifty people along a journey across America, Oliver Stone’s vision of a murder-obsessed society takes shots at everything from domestic violence to media saturation. Downey plays an Australian “journalist” who tracks Mickey and Mallory’s crime spree and glorifies their recent celebrity status to fuel his own reputation and image. With Oliver Stone specifically targeting the media as a reason for so many chaotic outbursts of violence, Downey carries this ideology to the extreme by playing a manipulative, media-hungry leech who gets what he deserves in the end. If you don’t remember the film, just close your eyes and go back into your psyche to find those images you wish to forget.

Based on Pulitzer Prize-winning author Michael Chabon’s novel of the same name, Wonder Boys is one of those small films that is loose on plot but filled with those idiosyncratic characters that make a movie memorable. Playing Michael Douglas’s editor, he walks a narrow line between heterosexuality and homosexuality and brings in the charm that makes his roles so memorable. Again, this film is crammed with a who's who of actors including a pre-Spiderman Tobey Maguire, Frances McDormand, Rip Torn, and Katie Holmes before XENU controlled her brain. It’s a movie about words and people who love to use them, and the soundtrack is not too shabby either, with a pop music score containing Neil Young and current works of Bob Dylan.

In a textbook example of foreshadowing, Robert Downey, Jr. plays a coke-addicted Beverly Hills brat who gets in way over his head. He owes 50k to his dealer, alienates his friends, and winds up in a classic downward spiral. He portrays all of this with a frightening reality that only a truly great actor or a guy on the way to annihilating himself with a wide array of substances can pull off. As he fits the bill on both counts, he's pretty convincing.