The eldest of Betsy and Doug Franco's three sons, James Franco drops out of UCLA after his freshman year to study acting at Robert Carnegie's Playhouse West. "All my friends looked at me with pity thinking I made a pretty poor move," Franco recalls to the Chicago Sun-Times. "But after you take the leap, you know in your heart if you made the right move or not."
Franco lands on the small screen in Judd Apatow's cult-hit series Freaks and Geeks, alongside comedic actors Seth Rogen and Jason Segel. He also makes his film debut with a bit part in the Drew Barrymore comedy Never Been Kissed and lands his first lead role in 2000's Whatever It Takes. Although the latter flops, Franco falls for costar Marla Sokoloff.
With his striking resemblance to screen icon James Dean, Franco headlines the eponymous TV biopic. "I took up smoking, like Dean, and cut off most of my friends," Franco tells the New York Times. "I'm doing everything I can to approximate his life." His performance earns him a lead actor Golden Globe, as well as an Emmy and Screen Actor Guild Award nominations.
Franco costars in Spider-Man as Harry Osborn, friend turned enemy of Peter Parker (played by Tobey Maguire). "I was auditioning for Peter Parker," he reveals to EW. "But it wasn't like the role of a lifetime for me. And the part I got had a lot more psychological push and pull than you would normally expect. So it worked out really well in the end." With Maguire and Kirsten Dunst, Franco reprises his role in the record-breaking trilogy, which grosses more than $1 billion in the U.S. alone.
Franco steps out with actress Ahna O'Reilly at the Las Vegas celebration of Maxim's 100th issue, but remains mum on his relationship. After five years together, Franco goes public with their split in Playboy in 2011. "It's over," he says. "We'd been living together in L.A. and then came to New York to go school for two years. Then I signed up for more school at Yale. I think that was it for her."
In between filming such flops as Tristan & Isolde and Annapolis, Franco returns to his studies at UCLA. "I am going back to school because I love being around people who are interested in what I'm interested in," he says. "That is the best way to learn." In 2008, he graduates with his bachelor's in English and enters Columbia University's graduate fiction-writing program, while studying directing at New York University and taking fiction writing classes at Brooklyn College.
Gucci chooses Franco to be the face of their new men’s fragrance. That December, the actor's good looks also score him his second honorable mention in PEOPLE's Sexiest Man Alive issue. But, as Franco tells Elle, he wasn't always at ease with his physical appeal: "In junior high and high school, sure, girls told me I was cute or whatever, but I was so shy I could never really make anything happen or cash in."
Franco reunites with Freaks and Geeks pals Apatow and Rogen for Pineapple Express. His performance as a pot dealer who loves his Bubby earns him a Golden Globe nod. Costar Rogen tells EW, "We put him in a grungy wig and some baggy clothes and...it's almost like he isn't even handsome in this movie." While Apatow explains, "You tell him, 'Okay, you're going to play a pot dealer,' and he comes back with a three-dimensional character you totally believe exists. He takes it very seriously, even when it's comedy." The film earns more than $87 million domestically.
Franco appears on the September issue of GQ, where he discusses his intense preparation for roles (earning his pilot license; shadowing a male stripper) and his regrettable film flops. "It's just sad for me, because I know I worked so hard, and I just feel like in some ways I kind of blew it," he says. "It’s just hard to get away from what I see as the stain of these bad movies."
In the Oscar-nominated biopic Milk, Franco plays Scott Smith, boyfriend of Harvey Milk–the first openly gay man elected to public office. "There haven't been a lot of male-housewife roles," Franco, who receives an Independent Spirit Award for his supporting role, jokes to GQ. "But I knew if I played it truthfully, I'd bring a political film to a human level."
BIOGRAPHY (top to bottom): Yearbook Library; Everett Collection; Columbia Pictures; John Sciulli/WireImage; National Photo Group; Courtesy of Gucci; Everett; Nathaniel Goldberg/GQ; Everett Collection