Born into a artistic family - his mother is a poet and his grandmother owns an art gallery - it's perhaps unsurprising that James ended up pursuing a career in Hollywood.
Acting wasn't always on the cards for the talented youth. Born in California on April 19, 1978, his academic strengths led him to enroll at the University of California as an English major. However, having developed a taste for the stage performing in school plays he dropped out after his freshman year against his parents' wishes to pursue a career as an actor.
His first break came in 1999 when he was cast as a leading role in the TV series Freaks and Geeks. He was subsequently cast as the lead in Mark Rydell's 2001 TV biopic James Dean. This role was to place him firmly on the Hollywood map as it ensured him a Golden Globe Award and nominations for an Emmy as well as a Screen Actors Guild Award.
The rising star cemented his popularity with the 2002 superhero film Spiderman. Cast as Harry Osborn, the best friend of Peter Parker, the success of the film led to him reprising the role in the 2004 and 2007 sequels. James also worked hard in the two years between the two Spiderman films, co-starring in the drama City by the Sea alongside Robert de Niro in 2002 and The Company alongside Neve Campbell in 2003.
In 2006 the actor won a Golden Globe nod for his performance as a stoner in The Pineapple Express. Although many believed he used method acting to perfect the role, James says that in reality he's very straightlaced: "I used to smoke weed, but I haven't done it in a long time. Everybody, even now, thinks, 'That guy is stoned.' It's just the way I talk, because I don't smoke weed. Somehow, there's something about me, the way I talk, that implies I'm on drugs."
2006 was also a year for love as James met Forgetting Sarah Marshall actress Ahna O'Reilly and the low-key couple have been dating ever since.
The actor has also proved his talents in many other aspects of the arts, publishing a collection of short stories called Palo Alto in 2010 as well as displaying his paintings in galleries in LA, in 2006. Two years later he moved to New York and enrolled at four graduate schools at the same time. In 2010 he started a PhD in English at Yale University.
Director Judd Apatow said of the star: "He's a very education-minded person. We used to laugh because in between takes he'd be reading The Iliad on set..."
Speaking of his decision to go back to school, James said: "I was really tired of acting. I was putting a ton of work in and not getting as much satisfaction out of it. So I just needed something else to focus my attention on, to take the pressure off. Turns out that I love school."
Notching up his list of awards, James won the 2008 Independent Spirit Award for his role opposite Sean Penn in Milk. The movie's producer Dan Jinks said of the star: "There's a sensitivity that exudes from him. He can without trying make you see into his soul. He makes it seem effortless."
His part as Sean's boyfriend, amongst other roles as a homosexual in the past, has caused many to question James' sexuality despite his longterm relationship. However the actor proved his sense of humour when he spoke of his and Sean's first kiss on-set.
The kiss "lasted a minute. It doesn’t sound like a long time but in front of 200 people it's a long time. You can't deny what's going on. I'm kissing Scipioli and it's still going on and it's not stopping and it was when he had a beard and the beard is scraping me. Afterwards we were like, "All right, how are those Raiders?"
In April, after the film was shot the two went to Coachella, a music festival in LA with James' girlfriend Ahna. "What do you think about me being the other girl?" Sean asked Ahna, according to James. "He would always ask me if my girlfriend was the better kisser."
His gripping portryal of trapped mountain climber Aron Ralston in 127 Hours won the actor an Oscar nod in 2010, ensuring his star is firmly on the rise.