The best Jake Gyllenhaal movies showcase how impressive the actor's career has been. He debuted in one of his father's (director Stephen Gyllenhaal) standout films, City Slickers and never looked back. Although initially typecast as a brooding, moody teen in angsty pictures such the twisty cult classic Donnie Darko, Gyllenhaal has since aggressively diversified his acting portfolio. In addition to taking on a wide breadth of challenging roles that have cemented his status as an undoubted A-lister, Gyllenhaal has also performed on Broadway, while picking up a mammoth 30 awards for his various portrayals.

Pulling together a definitive list of Gyllenhaal's movies requires a comprehensive view of his two-plus decade career, so only his films with major roles are considered. A lot of his work as a child saw him only appear briefly on screen and in minor roles. Once he began getting supporting and leading parts, Gyllenhaal's career took off...