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.

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