Focus Features

In Gus Van Sant’s biopic Milk, James Franco plays Scott Smith, an exquisitely unkempt hippie who first bewitches the dorky, middle-aged aspiring politico Harvey Milk (Sean Penn) with his mischievous grin, taut physique, and nonchalant disposition. It’s no easy feat standing out next to Penn, who oozes charisma and purpose as one of America’s first openly gay elected official, gunned down in 1977 after just a few months as one of San Francisco’s board of directors. But Franco, not one to slack on his aesthetics, plays it tacitly, as a free spirit at the cusp of adulthood. His character starts as a selfish lover with a proprietary claim on his boyfriend, evolves into a heartbroken ex who shares him with the world, and finally matures into a sensible torchbearer burdened and blessed by Milk’s martyrdom. His performance is nuanced and charming, and finally delivers on the mix of innocence, then innocence lost, that Franco has explored many times throughout his career.

Back when he was a student at UCLA in the ’90s, Franco reportedly studied acting to overcome his shyness. By the time he dropped out to pursue it full-time, he not surprisingly gravitated towards parts as socially conflicted outsiders. His efforts were often persuasive. Starring as the dejected teen Danny Desario in the 1999–2000 dramedy series Freaks and Geeks (co-produced by Judd Apatow), Franco embodied the cool alpha-male burn-out, imbuing him with a gentle temperament and disarming naiveté. (Even on set he was a bit of a loner. “I’ll admit I was not a team player,” he confessed to GQ.)

Gus Van Sant directing Franco in Milk

The actor elevated this knack for playing rebels to new heights when he won a Golden Globe in 2002 for his turn as the insecure-turned-reckless young icon in the TV movie James Dean. That performance, in turn, prompted Robert De Niro to handpick Franco for the role as his drug-addled son in 2002’s City by the Sea—another role as a maladjusted youth. Heck, even Franco’s character in the blockbuster Spider-Man films (2002 and 2004) oozed angst: Harry Osborn was a bratty privileged kid caught in a love-triangle with our hero and then decides to kill the web-slinger as payback for Daddy’s death.

With his deep brow and dramatic cheekbones, Franco appeared to effortlessly slide into these conflicted roles. But he also lent those parts a studied perspective. The actor comes from an erudite, artistic family: his mom a writer-editor, his grandfather a cartoonist, his grandmother an art-gallery owner. So, not surprisingly, he takes his craft seriously. For James Dean that meant so immersing himself so much in Dean’s lifestyle that Franco actually picked-up a pack-a-day habit; for City by the Sea, that meant living like a homeless kid for at least a few days. (“I slept on the streets and all that,” he said to GQ. “Was it necessary or not? Who’s to say? But I did it.”) And though he may have been bashful in the past, he isn’t hesitant about stoking any of his interests. Take his recent return to, and graduation from, UCLA, where he earned an English degree—before enrolling in creative-writing graduate courses at both Columbia and New York University. “I don’t sleep,” Franco, who also paints, told USA Today. “I have a lot of interests and a lot I want to get done.”

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In Gus Van Sant’s biopic Milk, James Franco plays Scott Smith, an exquisitely unkempt hippie who first bewitches the dorky, middle-aged aspiring politico Harvey Milk (Sean Penn) with his mischievous grin, taut physique, and nonchalant disposition. It’s no easy feat standing out next to Penn, who oozes charisma and purpose as one of America’s first openly gay elected official, gunned down in 1977 after just a few months as one of San Francisco’s board of directors. But Franco, not one to slack on his aesthetics, plays it tacitly, as a free spirit at the cusp of adulthood. His character starts as a selfish lover with a proprietary claim on his boyfriend, evolves into a heartbroken ex who shares him with the world, and finally matures into a sensible torchbearer burdened and blessed by Milk’s martyrdom. His performance is nuanced and charming, and finally delivers on the mix of innocence, then innocence lost, that Franco has explored many times throughout his career.

Back when he was a student at UCLA in the ’90s, Franco reportedly studied acting to overcome his shyness. By the time he dropped out to pursue it full-time, he not surprisingly gravitated towards parts as socially conflicted outsiders. His efforts were often persuasive. Starring as the dejected teen Danny Desario in the 1999–2000 dramedy series Freaks and Geeks (co-produced by Judd Apatow), Franco embodied the cool alpha-male burn-out, imbuing him with a gentle temperament and disarming naiveté. (Even on set he was a bit of a loner. “I’ll admit I was not a team player,” he confessed to GQ.)

Gus Van Sant directing Franco in Milk

The actor elevated this knack for playing rebels to new heights when he won a Golden Globe in 2002 for his turn as the insecure-turned-reckless young icon in the TV movie James Dean. That performance, in turn, prompted Robert De Niro to handpick Franco for the role as his drug-addled son in 2002’s City by the Sea—another role as a maladjusted youth. Heck, even Franco’s character in the blockbuster Spider-Man films (2002 and 2004) oozed angst: Harry Osborn was a bratty privileged kid caught in a love-triangle with our hero and then decides to kill the web-slinger as payback for Daddy’s death.

With his deep brow and dramatic cheekbones, Franco appeared to effortlessly slide into these conflicted roles. But he also lent those parts a studied perspective. The actor comes from an erudite, artistic family: his mom a writer-editor, his grandfather a cartoonist, his grandmother an art-gallery owner. So, not surprisingly, he takes his craft seriously. For James Dean that meant so immersing himself so much in Dean’s lifestyle that Franco actually picked-up a pack-a-day habit; for City by the Sea, that meant living like a homeless kid for at least a few days. (“I slept on the streets and all that,” he said to GQ. “Was it necessary or not? Who’s to say? But I did it.”) And though he may have been bashful in the past, he isn’t hesitant about stoking any of his interests. Take his recent return to, and graduation from, UCLA, where he earned an English degree—before enrolling in creative-writing graduate courses at both Columbia and New York University. “I don’t sleep,” Franco, who also paints, told USA Today. “I have a lot of interests and a lot I want to get done.”

Freaks and Geeks, James Dean, Pineapple Express

Part of feeding his youthful curiosities also meant revisiting comedy after spending the better part of seven years entrenched in weighty cinema. “I was fairly disappointed with some of the roles I had done,” Franco said to the LA Times. “I guess I’m proud of James Dean. But [2006 period romance] Tristan + Isolde or [that same year’s boxing drama] Annapolis are just—I worked really hard on those movies, but I just don’t like them. I don’t want to make those movies anymore.”

His career overhaul started with a cameo in Knocked Up, then a spot-on spoof of The Hills for Funny or Die. And most recently, he deadpanned his way through a fake Hollywood tribute orchestrated on the DL by Colbert Report writer Ben Karlin. But Franco really hit his stride in another Apatow project, August’s Pineapple Express. At this point, Apatow and his crew (including Seth Rogen and Paul Rudd) had pioneered their very own snarky man-child genre with films such as Knocked Up and The 40 Year Old Virgin. Franco, instead, made his clueless stoner/dealer a confused kid, ill-equipped to process stress and perennially seeking acceptance. “It seemed like Judd even realized…it’s not two idiots just smoking weed,” noted Franco to the Cinema Confidential. “It’s a relationship movie.”

Milk, too, is a relationship movie ensconced in a hagiography. Interesting then that Pineapple—an absurdist film that improbably goofs on drug-turf wars—would presage such a refined performance in his speedy return to drama. And though Franco is in, at best, half of the film, it’s telling that the actor—who not unlike many of his young characters, has finally come into his own—also shares second billing. Remarked Pineapple director David Gordon Green, of the actor’s voracious appetite for reading, to the L.A. Times: “He uses his time productively…packing a lot into life.” The same, it seems, can be said of his quietly powerful on-screen performance in Milk.

Nisha Gopalan is a senior editor at NYLON magazine. She has also written for The New York Times, Entertainment Weekly, Spin, Blender, and the Los Angeles Times.