If you were going to cast a beautiful man to play your off-center character, you can't do better than the strange and wonderful Johnny Depp. From Benny and Joon to Ed Wood to Dead Man, he's been remarkably reliable as a free spirit-on-film. And unlike the majority of working actors, Depp is constantly choosing directors at fertile, interesting points in their careers—Lasse Hallström (What's Eating Gilbert Grape), Terry Gilliam (Fear and Loathing in Las Vegas), and Ted Demme (Blow)—if they get on well enough, he's likely to work with them again, which speaks well for the actor. Depp's longest-running director-relationship, with Tim Burton, is a marriage of two simpatico minds.

Depp's career could be split into two eras: pre-Pirates of the Caribbean/post-Pirates. Before the hit/albatross-around-his-neck, Depp was an intriguing, beautiful actor best known for his eclectic, eccentric taste. After starting out as a 21 Jump Street teen-hunk, Depp went the weirdo route, refusing to cash in on his looks (he's mostly avoided romantic comedies) bringing his all to roles in small, heart-felt indies. Post-Pirates, where his camp take on Keith Richards proved the anchor of a surprise summer smash, he's veered towards headlining roles, bringing his idiosyncracies to stories with grand aims, fronted by visionary directors. This route has yielded some Oscar nominations and upped his profile considerably, giving the actor access to characters like Sweeney Todd and John Dillinger.

In his latest flick, Public Enemies, Depp teams up with kinetic director Michael Mann for a period piece about gangsters, molls, and Tommy guns (aka the "Chicago Piano"). As "Public Enemy #1," the legendary Dillinger, Depp headlines an all-star cast, including G-man-with-a-mission Christian Bale, Marion Cotillard, Billy Crudup (as a smarmy J. Edgar Hoover), Giovanni Ribisi, Lili Taylor, and many, many more. In Depp's capable hands, the elusively charismatic crook evades capture in shootout after shootout, much to the delight of the 1930s public, Dillinger's unlikely fans. This man is one smooth criminal.

Enemies sticks out in this summer of (sigh, America, do better) Transformers 2; it features stars clustered around a period piece helmed by a director best known for his bruising crime thrillers. It's a typical outta-left-field move for Depp, and as one of the world's finest movie stars, it will be interesting to see what films get made thanks to his choices. It's sure to be a mix of eclectic work—the actor just finished filming The Rum Diary, a Hunter S. Thompson adaptation—but as a full-fledged stah, he's clearly beyond his smaller and quiet 90s work. In the future, Depp will bring his unhinged energy to tentpole movies that need it. And as a true American original, he's going to make all those films far better than they have any right to be.
 

Benny and Joon

Dir. Jeremiah S. Chechik (1993)

Depp pulls from the Buster Keaton/Charlie Chaplin well in order to play the unbalanced Sam, a guy who finds himself taking care of the also-a-screw-loose Joon (Mary Stuart Masterson). It's a soulmate meeting of two crazy minds—the movie never specifies why Sam and Joon are mentally ill, it just romanticizes it—but they encounter trouble from both the outside world and Joon's worried brother Benny (Aidan Quinn). What's striking about Depp's work in this film (and many others) is that it likely read screamingly quirky on the page (and quirk was less cliché in 1993), but he's able to take a mad character, obsessed with the Hollywood greats, and give him dignity and authenticity. He's charming and believable.
 

What's Eating Gilbert Grape

Dir. Lasse Hallström (1993)

What's Eating Gilbert Grape is a wonderful novel written by Peter Hedges (put it in your library queue now) and it made a fantastic film, scripted by Hedges and directed by Hallström, in his second American flick, after the sublime My Life as a Dog brought him worldwide notice. (And, considering the amount of potential indie clichés in the film, how horrific could it have been if made in today's quirk-happy climate?) Hallström keeps a light hand, focusing on the chaos that surrounds Depp as the titular Grape—an overweight mom, a retarded brother (Leonardo DiCaprio in an excellent, Oscar-nominated performance that was robbed awards night). With all these pressures, Depp's Grape is nearly opaque, fading into the background—just trying to stay sane—and providing a quiet counterbalance to DiCaprio's bravura tics. It's a testament to Depp's lovely presence, and the solid film that surrounds it, that by the end of the movie, we understand that Grape can move beyond his family pressures and put together a sort of life.


 

Ed Wood

Dir. Tim Burton (1994)

It's kind of amazing to think about Depp's transformation in this film—he's accurately boyish and manic, nailing the rat-a-tat-tat patter of the time (by studying Mickey Rooney, Ronald Reagan, and Casey Kasem) in Burton's loving tribute to the worst director in the world. It's even more amazing to think about Depp as sad-eyed, nearly silent Edward Scissorhands in his previous (and very influential) collaboration with Burton, and how that differs from Ed Wood's loving farce. Depp was "depressed" about filmmaking at the time, and this film, and the chance to work with Martin Landau (who won an Oscar), rejuvenated his acting. The film was a flop, yet it received several Oscar nominations and was noted for its celebration of Wood's filmmaking—after all, even if he was "the worst filmmaker in the world," he thought he was making Citizen Kane.
 

Fear and Loathing in Las Vegas

Dir. Terry Gilliam (1998)

Alex Cox, the cult British director who made the biopic Sid and Nancy, had the first crack at a screenplay adaptation of Hunter S. Thompson's novel, but as the film made its way out of development hell, it fell to Gilliam. Thompson suggested Depp as the only person who could play his alter-ego, Raoul Duke, and the two men forged a legendary friendship, thanks to this film. (Read Depp's Rolling Stone eulogy for Thompson, "A Pair of Deviant Bookends.") Depp was one of the head mourners at Thomspon's funeral, and—a testament to his movie-star power these days—he's gotten a production of Thompson's The Rum Diary off the ground, to be directed by Withnail and I's Bruce Robinson (who at one point turned down Fear and Loathing because he didn't think it could be captured on film).

Now, Fear and Loathing, the film, has a certain cult cache. It is filmed a bit like a Tony Scott/MTV film, with quick cuts and surreal worlds and Depp leading the way, giddily. Whether the film is appealing or not depends on your opinion of Thompson and the level of your drug use. The trivia page on IMDB for this film is fascinating, of course.
 

Dead Man

Dir. Jim Jarmusch (1996)

Jarmusch's film died a quick death (ironically!) in the theaters, but it's getting a revival on DVD. And perhaps that's a testament to the talent involved: the silvery, black-and-white cinematography, Neil Young's haunting score, and Depp as banker William Blake. Essentially, the movie's a big metaphor. Blake's journey in this film is like the journey to the underworld, with many allusions, starting with the character's name, to poet William Blake. Whether you'll like it depends on your mood for "filmed poetry." Jarmusch's next narrative, Ghost Dog: the Way of the Samurai, comes from a similar spot, but in this case, the philosophy is countered with samurai awesome-ness.

See it on the big screen when Dead Man screens at the BAMcinematek on Thursday, June 2, at 6:30 pm.
 

Blow

Dir. Ted Demme (2001)

The man who started the cocaine import business in America, George Jung, grew up in small-town Massachusetts (the ever blue-collar shoe factory town of Weymouth) and went west to California, where he became a marijuana dealer, and eventually one of the world's top cocaine distributors. Demme's film, adapted from Bruce Porter's book BLOW: How a Small Town Boy Made $100 Million with the Medellin Cocaine Cartel and Lost It All, hits the beats you'd expect from a drug biopic—Jung pursues money and hedonism, Jung gets in jail, etc.—but with Depp at the center, sporting a decent, subtle Massachusetts accent, it stays compelling. Penélope Cruz acquits herself in a screamy role that'd be hard for anyone to play, but it's interesting to see a very young Emma Roberts as Depp and Cruz's child. Sadly, this was Demme's last narrative film (with the underrated Beautiful Girls as one of his best); he passed away from a heart attack a year later. An autopsy found cocaine in his system.
 

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