8 Times Jake Gyllenhaal Fought His Own Hotness (And Won)

8. Donnie Darko (2001)

Before Jake appeared as the titular Donnie Darko in this indie hit, he was best known as the kid in City Slickers, the kid in Homegrown and the slightly older kid in October Sky. By 2001, Jake was a chiselled 21 year old babe with all the opportunity in the world to transition from adorable child actor to desirable leading man. Instead he did... well... this. Released in 2001, Donnie Darko had an amazing cast - including Jake€™s similarly babing sister Maggie - and was surprisingly successful given that no one could actually explain what the hell it was about. Donnie Darko is a pretty good movie that I€™ve been pretending to understand since watching it at a sleepover 12 years ago. But Jake spends the whole thing with his hair matted down and his skin vaguely sheen-y, perfecting the look of €œGuy who sits alone on the bench seat at the back of the bus€. Frank, the giant apocalypse bunny, had more sex appeal than him (mainly among furries, sure, but that€™s still a pretty decent-sized demographic).
Contributor
Contributor

Brydie is an Australian writer and performer living in London and she complains exactly the same amount about the weather as every other Australian living in London. Yes, that is her natural lip colour, no, she will not be taking any further questions at this time.