3. The Good Girl (2002, dir. Miguel Arteta)
While most people remember The Good Girl as the first (and only) genuinely emotional performance by Jennifer Aniston, the film truly works because of Gyllenhaal’s convincing work as a mopey stock boy who adopts the name Holden (as in Holden Caulfield) to reflect his alienation. With a wonderful script by Mike White, The Good Girl is a quiet and tender story about exploration and temptation that follows Justine (Aniston) and Holden as a flirtation turns into an affair with disastrous results.
Gyllenhaal is perfectly cast as Holden, thanks to his big, puppy dog eyes and naturally soft voice. He plays Holden as a dreamer who’s blinded by his desire for a life with Justine. While early on Holden seems to be mature and wise beyond his years, Gyllenhaal unleashes his true childish selfishness as the film progresses. The Good Girl was one of the first movies to gain Gyllenhaal mainstream attention thanks to Aniston’s fame. He would use this opportunity to launch an ever-evolving and impressive career.