Career Watch is a regular column by veteran film reporter and Moviefone guest-blogger Anne Thompson looking at the career of a major Hollywood star, analyzing the moves they've made thus far and offering career advice on where they could or should head from here. This week: newly minted action star Jake Gyllenhaal.

Signature line:
"I wish I knew how to quit you," says Jack Twist to Ennis del Mar, in 'Brokeback Mountain.'

Career Peaks: Raised in L.A. by director Stephen Gyllenhaal and screenwriter Naomi Foner, Gyllenhaal popped up as a teen actor in the 1999 true story 'October Sky,' followed by his breakout role in Richard Kelly's strange 2001 psycho-drama 'Donnie Darko,' which went on to attain cult status. Gyllenhaal burnished his acting cred by playing a series of sensitive, sweet young men in low-budget indies such as 'The Good Girl,' 'Proof' and 'Lovely & Amazing.' While it was not Gyllenhaal's finest hour, the 2004 disaster epic 'The Day After Tomorrow' marks the actor's biggest global hit to date: a total $544 million. He scored critical raves for two 2005 films, Gulf War actioner 'Jarhead' and Ang Lee's tragic gay romance 'Brokeback Mountain,' opposite Heath Ledger, which earned $178 million worldwide. Career Watch is a regular column by veteran film reporter and Moviefone guest-blogger Anne Thompson looking at the career of a major Hollywood star, analyzing the moves they've made thus far and offering career advice on where they could or should head from here. This week: newly minted action star Jake Gyllenhaal.

Signature line:
"I wish I knew how to quit you," says Jack Twist to Ennis del Mar, in 'Brokeback Mountain.'

Career Peaks: Raised in L.A. by director Stephen Gyllenhaal and screenwriter Naomi Foner, Gyllenhaal popped up as a teen actor in the 1999 true story 'October Sky,' followed by his breakout role in Richard Kelly's strange 2001 psycho-drama 'Donnie Darko,' which went on to attain cult status. Gyllenhaal burnished his acting cred by playing a series of sensitive, sweet young men in low-budget indies such as 'The Good Girl,' 'Proof' and 'Lovely & Amazing.' While it was not Gyllenhaal's finest hour, the 2004 disaster epic 'The Day After Tomorrow' marks the actor's biggest global hit to date: a total $544 million. He scored critical raves for two 2005 films, Gulf War actioner 'Jarhead' and Ang Lee's tragic gay romance 'Brokeback Mountain,' opposite Heath Ledger, which earned $178 million worldwide.

Awards Attention: 'Donnie Darko' earned Gyllenhaal an Independent Spirit nomination as Best Male Lead, and he collected the London Evening Standard Theater Award for outstanding newcomer for the 2002 play 'This is Our Youth.' He won the supporting actor BAFTA for 'Brokeback Mountain,' and while many thought he should have joined Ledger in the best actor category, 'Brokeback Mountain' earned Gyllenhaal his first and only Oscar nom, for Best Supporting Actor.

Latest Misfire: This summer's $200-million would-be franchise 'Prince of Persia: The Sands of Time,' a well-made but featherweight B-movie adventure from Jerry Bruckheimer and Mike Newell, failed to launch. After losing 'The Dark Knight' to Christian Bale, 'Spider-Man' to Tobey Maguire, and 'Avatar' to Sam Worthington, Gyllenhaal had finally landed a major action role in a summer tentpole, or so he thought. Instead, many reviewers argued that Gyllenhaal was miscast, and despite his buffed-up physique, failed to carry the action adventure. While some women reviewers liked him -- AP's Christy Lemire describes his "engaging presence" and "those big, blue eyes, that goofy smile - and that sweetness helps keep the mood light," while The New York Times' Manohla Dargis writes that "a few hours of Mr. Gyllenhaal jumping around in leather and fluttering his long lashes has its dumb-fun appeal," other critics cited Gyllenhaal's "doubts and insecurities," "puppy-dog eyes," "self-deprecation" and "hangdog demeanor." Not what you expect from a rugged action hero.

Biggest Problem: 'Prince of Persia' failed to open well -- and didn't change the popular perception of Gyllenhaal as a likable leading man best suited to naturalistic dramas. There's still a sizable gap between the rising star's acting bonafides and his ability to put butts in seats. While Gyllenhaal earned excellent reviews in recent dramas 'Brothers,' 'Rendition' and 'Zodiac,' the films disappointed at theater wickets.

Major movie stars have a hint of danger about them; Gyllenhaal, who hits 30 in December, is one of many boyish American leading men who will earn needed gravitas as they age. No one had any trouble buying him as a well-muscled grunt with a shaved head in the realistic Gulf War drama 'Jarhead,' but audiences did resist him in breastplate and leather in a big-budget Disney studio sword-and-scandal flick. Male action stars tend to appeal to men, while Gyllenhaal's primary fan-base is female.

Current Gossip: After Gyllenhaal broke up in 2004 with the love of his life, actress Kirsten Dunst, he continued an on/off relationship with her for two years. Post-'Brokeback,' he good-humoredly shrugged off speculation about his sexuality, including a rumored affair with pal Lance Armstrong. Gyllenhaal met Reese Witherspoon in 2006 on the set of 'Rendition,' soon after her divorce from Ryan Phillippe, but that relationship ended at Thanksgiving. Gyllenhaal insists that he enjoys being single. During filming in Montreal on 'Source Code,' he hit the town with frisky Australian actress Isabel Lucas ('Transformers: Revenge of the Fallen').

Biggest Assets: A gifted actor with impressive range, Gyllenhaal has more options than ever. While 'Prince of Persia' was a setback for him, he may have moved the needle slightly. In the movie, he is charming, sexy and physical (with a boost from stuntmen and digital effects) in the role of a wily, athletic young prince who is scooped off the street as a kid by a kindly king. And he even manages a Cockney accent amid an ensemble of Brits. All it took for Matt Damon to become a matinee idol was the 'Bourne' franchise -- which suddenly revealed him as an athletic, dangerous action star. And Hugh Jackman was just a song-and-dance man before he took on Wolverine in the 'X-Men' franchise. "It's about the right person in the right role at the right time," says one studio casting director, who points out that it took Tom Cruise fifteen years to turn into the star of 'Mission: Impossible.'

Next Step: It doesn't look like we're going to see David O. Russell's long-on-the-shelf 'Nailed' anytime soon, which co-stars Jessica Biel and Catherine Keener. Embattled financeer David Bergstein's money woes have left the film gathering dust with a crucial scene still left to film. Gyllenhaal has completed Ed Zwick's romantic comedy 'Love and Other Drugs' (November 24), playing a Viagra salesman in 1995 who falls for Anne Hathaway ('Brokeback Mountain') as well as Duncan Jones' spy thriller 'Source Code,' in which Vera Farmiga sends him traveling through time. Michelle Monaghan co-stars in the film, which is due in 2011.

Career Advice: Look for great material with directors you respect, and don't abandon the indies for studio paydays. "Find parts that ask you to show things to audiences you haven't seen before," adds the casting director. "It's not about one movie. He's in for a body of work over the long run." So far, Gyllenhaal has chosen fairly well, without falling prey to godawful studio formula fare. I like the idea of him playing middle-aged Joe Boyd, who sells his soul to the devil to become a young baseball slugger in 'Damn Yankees,' a great musical with an emotional kick. (Gyllenhaal studied singing when he tried out for 'Moulin Rouge.') And Joe Namath has approved his casting as Broadway Joe, the great New York Jets football star, which Gyllenhaal wants to be "bad-ass," he told MTV, "so it's taken a little while. I'm committed."

Anne Thompson -- who has served as Deputy Editor of Variety.com and The Hollywood Reporter, West Coast Editor of Premiere and Senior Writer at Entertainment Weekly -- writes a daily blog on indieWIRE, Thompson on Hollywood. You can check out some of her latest posts here:

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