I was all prepared to be the pretentious douche who, when ranking Robert Downey, Jr.’s five best roles, weighed the list heavy with pre-rehabbed Downey. Until Iron Man, Downey had always been a brilliant but under-appreciated actor. Even still, most of his pre-comeback script choices were spotty, at best. He used to excel at the smarmy sleazy guy with the occasional bit of charm (The Pick-Up Arist, Two Girls and a Guy) and, up until around 1995 — when his career went off the rails — he made a lot of bad to mediocre guilty pleasure movies, like Heart and Souls, Air America, Chances Are and Only You (if he wasn’t snorting coke before Only You, that movie probably would’ve driven him to it). He was trying really hard, I suppose, to be a romantic comedy leading man, and had drugs not taken over his life, it’s sad to think that he might have forever been rutted in Matthew McConaughey territory.
Granted, he had some fine roles during that time frame, too (one of which is mentioned below). He was great as the Geraldo-type sleazy journalist in Natural Born Killers and delightful in both Home for the Holidays and Soapdish. It’s best, however, to treat the years between 1995 and 2000 as the black-out years. Downey must have been so balls-out high during that period that he took anything that came with an advance in cocaine: Mr. Willowby’s Christmas, One Night Stand, Danger Zone, Restoration, Hugo Pool, U.S. Marshall, The Gingerbread Man, In Dreams, and Friends and Lovers with Stephen freakin’ Baldwin.
Unlike some actors (Robin Williams), cleaning up was not only good for Downey’s lifespan; he’s improved as an actor, too. Part of that, I suspect, is that he’s been given better roles to work with, but maybe having a clean head has simply made him a better actor and the toxic period in his life has given him something from which to draw his talents.
Here are, not RDJ’s best movies, but his best roles:
5. Wonder Boys: Goddamn, I love this movie. It’s really Michael Douglas and Tobey Maguire’s film, but Robert Downey, Jr. has such an electric and integral role as the gay literary agent, that it’s as much him — and the soundtrack — that you take away from the movie than it is Douglas and Maguire. Wonder Boys came out during that period in Downey’s life where he was in and out of rehab; in fact, I believe that Downey was actually in prison when Wonder Boys was released and it was his role in this film that reminded us of what a loss to the film world it would be not to have him around.
4. Chaplin: I didn’t love Chaplin, the movie — it was overly long and still didn’t manage to properly cover Chaplin’s life — but Downey’s depiction of the silent film star deservedly elicited an Oscar nomination. Downey, theretofore known best for frivolous roles in frivolous films (Weird Science, Johnny Be Good, among others) completely sold the character, effortlessly capturing the essence of Chaplin — the heartbreak, the joy, and the sadness — while deftly mimicking the gestures. It really was a mediocre film, but Downey brought even the smallest moments to life.
3. Tropic Thunder: It’s tempting to move this to number two on the list, because RDJ was so flat-out phenomenal as Kirk Lazurus, the dude playing the dude disguised as another dude. Tropic Thunder wouldn’t have been a particularly good film without RDJ (and the Cruise cameo). I don’ think there are many actors in the world who could’ve pulled that off, especially without offending half of America. But RDJ excellently captured the buffoonery of his character without turning his character into a buffoon. If the rest of the film had been as good as RDJ’s performance, he most certainly would’ve converted that Oscar nomination into a win.
2. Iron Man: Tony Stark represents the third evolution of the action hero since the ’80s, from the Schwarzenegger/Stallone brawny type to the compact martial arts bad ass Bourne type to what is essentially a charismatic, narcissistic geek. Tony Star is a better looking Steve Jobs — a gadget geek slash Playboy. He’s never an impressive action star outside of the suit, he’s just a brilliant scientist with a lot of money and charm. You can rain on my RDJ mancrush as much as you’d like — and really, calling me “gay” is about the least insulting thing anyone could ever say — but it’s not about that. A gay crush on RDJ would be a lot more dignifying than what I have, which is a little boy idol worship. I don’t want to be with RDJ, I want to fucking be him, and Iron Man pushes all those buttons. He’s Superman, only he gets to play with gadgets and sleep with anyone he wants. As a dude, what’s not to love about that guy?
1. Kiss Kiss, Bang Bang: Kiss Kiss Bang Bang is not only RDJ’s best role, it’s his best movie, too. This was the comeback role that the little-seen The Singing Detective was not. It was the perfect blending of the old (sleazy charming) and the new (endearingly charming, light on the smarm). It was a deceptively challenging role, too. RDJ played a petty thief playing an actor shadowing a real detective ahead of his screen test for a role as a detective (another dude disguised as another dude role). There’s a lot of layers, there, and RDJ pulled it off with absolute magnetism. It’s a great movie, from start to finish, and even Val Kilmer is excellent in it, but it’s RDJ and his kinetic conversational energy that pulls you in and envelopes you. Brilliant role. Brilliant movie.