Iron Man 3, which will be released in theaters this Friday, is already projected to break $1 billion in worldwide grosses. Consider it another victory lap for Robert Downey, Jr. The actor, who has become the face of the Marvel franchise, has now reached such heights of superstardom that it’s hard to believe that Jon Favreau (who directed the first Iron Man) had to fight so hard to convince the studio to cast him. But Downey was not always such a sure thing.

Actors are used to ups and downs, but Downey’s career has been truly tumultuous. He started out in teen comedies like Weird Science and Back to School, did a short, unmemorable stint during one of Saturday Night Live’s dead periods, became Hollywood’s hottest young thing in films like Chaplin, bottomed out with drugs and alcohol, then worked his way back to superstardom.

But much of his earlier work has now been forgotten, hidden by the bright glare of iconic roles like Tony Stark and Sherlock Holmes. His new stardom brings its own constraints, and it seems unlikely we’ll ever see him in the type of nuanced roles he has played so well in the past. With Iron Man 3 out this week and The Avengers 2 on the horizon, let’s take a moment to look back at some of the best Downey performances that have been overlooked. If it wasn’t already obvious, these should go on your queue immediately.

Kiss Kiss Bang Bang (2005)

The reason I know Iron Man 3 is going to be good is because its directed by Shane Black, whose only previous directorial effort is this 2005 post-modern film noir starring Downey and Val Kilmer. Downey plays Harry Lockhart (tremendous noir name), a small-time New York crook who gets mistaken for an actor and is flown to Los Angeles for a movie screen test  – although his acting career quickly falls by the wayside when he gets caught up in a complicated case involving a gay private eye (Kilmer), a slimy millionaire (Corbin Bernsen), and Lockhart’s old high school flame (Michelle Monaghan). Downey’s rapid-fire delivery is a perfect fit for Black’s crackling dialogue, and the movie has more surprises in 10 minutes than an entire summer’s worth of big-budget blockbusters. See it. See it now.

 

Chances Are (1989)

Downey plays Alex Finch, the kind of nice, young man every good girls wants to bring him to meet her mother. Mary Stuart Masterson plays such a girl in this underrated gem that evokes a bygone era’s screwball comedies – with a karmic twist. She meets and falls for Alex, only to discover that he is the reincarnation of her dead father. When Alex walks into their home, he starts having flashbacks, and before long, he has fallen in love with Miranda’s mother (Cybill Shepherd) – the dead father’s wife. Downey and Shepherd proves adept at both physical comedy, witty banter, and palpable sexual tension. Underneath it all is an emotionally resonant and romantic story about finding love after loss.

 

Heart and Souls (1993)

Heart and Souls could be seen as a companion piece to Chances Are. In the latter, his character is dealing with a past life. In Heart and Souls, he’s dealing with more than one. Downey plays a cocky young business man who accidentally becomes the vessel for four people killed in a bus crash. Given a chance to fix the great mistakes in their lives, each of them uses Downey (sometimes physically embodying him) to track down friends, family members, and old flames. The supporting cast is terrific (the “ghosts” are played by Charles Grodin, Kyra Sedwick, Alfre Woodard, and Tom Sizemore), but Downey shows his comedic versatility when he has to “play” each of the other actors. Here’s a good example:

 

Two Girls and a Guy (1997)

Downey plays Blake Allen, a narcissistic actor/singer who gets confronted in his apartment by the two women (Heather Graham and Natasha Gregson Wagner) he has been simultaneously dating. After a few minutes of screaming and yelling, the movie shifts to an interrogation, as the two women try to figure out just what is wrong with this guy they thought they loved so deeply. Blake spends most of the film trying to weasel his way out of the predicament,  while keeping his sense of righteousness intact. As the title implies, the film has strongly sexual themes, but Toback is far more interested in these characters’ emotional entanglements – not their physical ones. It becomes an exploration of the psyche of a man whose charisma covers some very deep psychic scars.

NOTE: I really wish a clip of this film’s “mirror scene” were available somewhere online, but watch the movie, and you’ll know what I mean. There have been some great mirror scenes in the past (Taxi Driver and Wanderlust – very NSFW – spring to mind, for very different reasons), but this one tops them all.  There may not be a better 90 seconds of acting in the history of film. Go find it. For now, here’s the trailer.

 

Zodiac (2007)

Released the year before Iron Man, Downey plays second fiddle to star Jake Gyllenhaal as a reporter at the San Francisco Chronicle following the story of the Zodiac serial killer. One of America’s most famous unsolved murders, the Zodiac terrorized citizens of the Bay Area and captivated amateur sleuths by warning newspapers in advance of his crimes. Gyllenhaal’s naïve cartoonist gets the bulk of the screen time, but Downey makes a larger impression as the reporter who works the story to the bone, eventually becoming a target himself. In this terrific scene, we see what his work has wrought:

 

Further Viewing:

Chaplin (1992) – The film is not great, but Downey is. He magically conjures up the spirit of Charlie Chaplin, the world’s first film star, and effortlessly recreates some of his most famous physical gags.

Less than Zero (1987) – In this adaptation of Bret Easton Ellis’s famous novel, Downey commands the screen as a charismatic, young drug addict who falls prey to the temptations rampant in Los Angeles in the 1980s.

Wonder Boys (2000) – This was one of Downey’s comeback roles, after his stint in prison. He plays the beleaguered literary agent to a famous writer who is struggling to write a follow-up to his hugely successful debut. It’s probably the best film ever made about writers.