The Best Movie Ever | Robert Downey Jr.

Robert Downey Jr. is one of the most successful, profitable actors on the planet. But it was not always thus. After a promising start in the 1980s and an Oscar-nominated turn in the respectable biopic Chaplin, Robert Downey Jr. tested the industry’s patience with bad behavior and unreliability. He’s never stopped making movies, and he’s always made good ones, but he’s had one of the most erratic careers of any actor in the history of cinema.

Also: Rapid Reviews | ‘Captain America: Civil War’ in :60 Seconds (Exclusive Video)

But which movie is his best? With Captain America: Civil War coming out this weekend, we wanted to take this opportunity to look back at the career of Iron Man himself, and ask our resident film critics – Crave’s William Bibbiani and Witney Seibold, and Collider’s Brian Formo – which film represents the pinnacle of Robert Downey Jr.’s career.

They can only pick one film, and none them picked a Marvel movie. Take a look at their picks, let us know your favorites, and come back next Wednesday for another all-new and highly debatable installment of The Best Movie Ever!

Brian Formo’s Pick: Wonder Boys (2000)

Paramount Pictures

Robert Downey Jr. went into rehab for drug addiction without ever really playing the bad guy role. Even when he was losing control in his personal life he was always a charming actor. He generally didn’t play admirable roles, either, his charm was just natural. Even when he lets his best friend convince him to go have beers with young women they’d just met in Short Cuts, and he sees his friend beat one with a rock, he somehow emerges as a good guy, wrong place fella. But the public was aware of his private demons and even though his personal choices never did anything to audiences, there might not be a better apology-movie-valentine than his performance in Wonder Boys.

In Wonder Boys, Downey Jr. plays a down on his luck publisher who had once discovered a brilliant writer who never wrote the follow-up novel (Michael Douglas) that his career desperately needs. He hides his personal feelings of diminishing returns through sheer confidence. We meet his Crabtree on the moving walkway at the airport as he’s convincing a transgender passenger to join him for drinks. This is Downey Jr’s best performance because during a time when Hollywood wanted him to apologize for his past and the director, Curtis Hanson, had to take out an immense insurance policy on the actor because the studio was worried about a relapse, Hanson cast Downey Jr. as a man who does not need to apologize. Not for his sexual fluidity, nor his badgering of a writer, because he wants to help others flourish. And we want to see him to flourish, too.

As an actor in this delightful showcase of creatives, Downey Jr. allows Douglas, Tobey Maguire, Frances McDormand and local unknowns to each get a great scene in his presence. He plays off them. He charms the room. Just like he always has, even during darker periods in his personal life. And now he’s one of the world’s biggest stars. Don’t call it a comeback. He’s been this way for years.

Witney Seibold’s Pick: Kiss Kiss Bang Bang (2005)

Warner Bros. Pictures

Robert Downey Jr. is perhaps one of the most notable performers of his generation. He was once considered an adjunct to the Brat Pack, has played a sexual dynamos, sensitive souls, and, most frequently, charming cads. No matter what his role, Downey seems at ease. All this despite years of struggling with addiction and the occasional arrest. He has starred in ambitious art films like Natural Born Killers, actorly indies like Two Girls and a Guy, and stalled Hollywood non-starters like Gothika. In 2003, Downey kicked the habit (he’s been sober ever since), and began looking for the project that would make him a mainstream star again. He eventually settled on a comedy noir project by equally-struggling once-wunderkind Shane Black called Kiss Kiss Bang Bang. 

It’s difficult to describe the delights this movie provides. The characters are endlessly witty, wry, and cynical. Downey plays a low-rent criminal who, through a bizarre set of circumstances, ends up employed by a movie studio, and the protégé of a gay private investigator played by Val Kilmer. Shane Black is expert in writing fast, witty, sarcastic dialogue, and Downey has spent a career mastering the very same type of wit, so they were a perfect match. In many ways, the Downey persona finally matured with this film. It’s hilarious, has a great old-fashioned noir story, and features great performances from Downey, Kilmer, and the criminally underused Michelle Monaghan. 

Kiss Kiss Bang Bang flopped, to the dismay of everyone involved. It had since grown its audience, luckily, and Downey managed to find his mainstream success in the Iron Man films and the Sherlock Holmes films. This was essentially a display of Downey’s potential energy. Locked and loaded and ready to fire. 

William Bibbiani’s Pick: Kiss Kiss Bang Bang (2005)

Warner Bros. Pictures

Robert Downey Jr. is one of those actors everyone wanted to love, even when he pushed us away. And indeed, he pushed us away for well over a decade, after well-publicized personal problems turned a once promising, Oscar-nominated acting career into a series of small, scattershot supporting performances in films that were mostly unworthy of his talents. (Remember In Dreams? You don’t really have to.)

And although Iron Man became the film that defined Robert Downey Jr.’s career – for better or worse – it was Kiss Kiss Bang Bang that tossed that ball underhand in the first place. It’s one of those amazing movies that doesn’t actually make money, but so wildly impresses everyone who sees it that A) it changes the entire industry, and B) goes on to become a classic.

It’s Robert Downey Jr.’s movie, but only because Shane Black lets him have it. This is essentially the film that The Last Boy Scout was obviously supposed to be. A slick detective story in a milieu that is, nowadays, usually dedicated to action for its own sake. It is a film in which being a fast-talking sleaze has more entertainment value than an explosion. And nobody is a better fast-talking sleaze than Robert Downey Jr.

And so Kiss Kiss Bang Bang, with its brilliant screenplay and unconventional performances, paved the way for that Iron Man movie everyone liked so much. It reminded us that we love Robert Downey Jr., even when – and sometimes especially because – he’s a bit of a cad. He pushed us away, but we couldn’t stay gone forever, not when he turns out to be this damned charming.

Previously on The Best Movie Ever:

Top Photos: Warner Bros. Pictures / Paramount Pictures