After fifteen months of training, he began auditioning in Los Angeles, California, and got his first break in 1999, after he was cast in a leading role on the short-lived but well-reviewed television series Freaks and Geeks. Franco has since described the series as "one of the most fun" work experiences that he has had. Franco's first major film was the romantic comedy Whatever It Takes (2000), where he met his co-star, now ex-girlfriend Marla Sokoloff. He was subsequently cast as the title role in director Mark Rydell's 2001 TV biopic James Dean. Ken Tucker of Entertainment Weekly wrote: "Franco could have walked through the role and done a passable Dean, but instead gets under the skin of this insecure, rootless young man." He was distinguished with a Golden Globe Award, as well as being nominated for an Emmy Award and a Screen Actors Guild Award.
Franco was originally considered for the lead role of Spider-Man/Peter Parker in the film version of Spider-Man, but was instead cast in the supporting role of Harry Osborn, the son of the villainous Green Goblin. The success of the Spider-Man film led him to reprise the role in two sequels, Spider-Man 2 (2004) and Spider-Man 3 (2007). Franco was cast in the 2002 drama City by the Sea. Franco has also co-starred with Neve Campbell in Robert Altman's The Company (2003). He appeared in the 2005 war film The Great Raid, in which he portrayed Robert Prince, a captain in the United States' Army elite in the sixth Ranger Battalion, to plan the rescue of prisoners of war from the Cabanatuan prison camp.
In 2006, Franco co-starred with Tyrese Gibson in Annapolis and played legendary hero Tristan in Tristan & Isolde, a dramatization of the Tristan and Iseult story also starring English actress Sophia Myles. He then trained with the stunt team "The Blue Angels" and received a pilot's license in preparation for his role in Flyboys, which was released in September of 2006; the same month, Franco appeared briefly in The Wicker Man, a horror film starring Nicolas Cage, who directed him in Sonny. Franco made cameo appearances in The Holiday and Knocked Up. He was also featured in the mockumentary, "Finding Ben Stone", on the two-disc edition of Knocked Up, where he gets fired from the lead role.
He starred in the 2008 film Pineapple Express, a comedy co-starring and co-written by Seth Rogen and produced by Judd Apatow, both of whom worked with Franco on Freaks and Geeks In the New York Times review of the film, critic Manohla Dargis wrote: "He’s delightful as Saul, loosey-goosey and goofy yet irrepressibly sexy, despite that greasy curtain of hair and a crash pad with a zero WAF (Woman Acceptance Factor). It’s an unshowy, generous performance and it greatly humanizes a movie that, as it shifts genre gears and cranks up the noise, becomes disappointingly sober and self-serious."
Franco has been signed to star opposite Sean Penn, Josh Brolin, and Emile Hirsch in Gus Van Sant's upcoming Harvey Milk bio-pic Milk. On September 20, 2008, James hosted Saturday Night Live.
Franco has also starred in a number of humorous viral videos. One such video purports to show the actor being fired from the film Knocked Up, which was directed by Apatow. The video currently has over 500,000 views on the comedy video-sharing site Funny Or Die. Franco also hosts a satirical series of acting lessons, Acting with James Franco, also on Funny Or Die. Franco's latest viral comedy appears to be a parody of a Hollywood tribute video.
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Pineapple Express 
Nights in Rodanthe
Milk
Howl
