RANKED! The Best Movie Roles of Jake Gyllenhaal From ‘Brokeback’ to ‘Donnie Darko’ (Including His New Film ‘Guilty’)

Can you imagine living next door to Jake Gyllenhaal? Every time you stepped outside to check the mail and ran into him, you’d never know which Jake you were going to get.

Such is the range of an actor who has played everything from a lovesick bubble boy to an unhinged existential superhero (all in the same year).

Love him or hate him, we can all agree Gyllenhaal has covered a lot of ground since his first movie role as Billy Crystal’s cringe-filled son in City Slickers. And despite being a handsome guy-next-door type with striking Siamese cat eyes, Gyllenhaal has effortlessly sidestepped the rom-com rut many up-and-comers fell into during the early aughts by taking left-field roles in small-budget indie flicks.

His need for slightly dark, character-driven stories even shines through in franchise blockbusters (Mysterio, anyone?). He is a master of naturalistic humor and dread in equal measure.

Now at the tender age of 40, Gyllenhaal continues his 20-plus-year stride with a role in Antoine Fuqua’s upcoming thriller about a 9-1-1 dispatcher who gets sucked into a phone call that’s more than meets the eye:

Sure, it seems a little pointless to worry about a possible kidnapping when the world is on fire, but Gyllenhaal sells it like such a pro we can’t help but buy what he’s selling. His chiseled jaw and anxiety-riddled eyes nail it again and again. Now with over 50 movies under his belt, it’s time we ranked the top ten. Buckle up.

Cover Photo: L. Cohen (Getty Images)

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