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.
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.