(5) Enemy (2013)
In Denis Villeneuve’s stylish thriller, Jake plays dual roles as Adam and Anthony, two people who look almost identical but are distinctly different in personality. Here Jake succeeds in the best way possible to offer two interpretations that, without stylistic devices or overacting, differ enough for us in the audience to distinguish them, but not so much that it feels flat or implausible. There is subtlety here in his acting that works wonders for both characters.
(4) Brokeback Mountain (2005)
He told us afterwards that everyone, including his agent and manager, advised him against accepting the role of Jack Twist in Ang Lee’s remarkable drama, but almost 20 years later we know with great certainty that it was, of course, heaven’s luck that he refused to listen. Because here, of course, Jake is brilliant. Gyllenhaal portrays Jack as an initially cheerful, curious, bouncy and idealistic young man who slowly but surely grows into the person he condemned as a young man. Anger, regret and disappointment fill his broken heart in a performance that still enchants after all these years.
(3) Donnie Darko (2001)
Playing a sleep-deprived teenager with no ambition, who wants nothing more than to rebel – while large parts of life collapse shortly after an airplane engine crashes into the house where you live, is obviously easier than mixing that interpretation with a hypnotized, homicidal young man who is asked, via a ghost in a rabbit costume, to carry out all sorts of acts of violence in this remarkable classic. Gyllenhaal’s performance in Donnie Darko will forever be one of those breakthrough roles that we remember with joy and fascination.
(2) Prisoners (2013)
There is an inherent darkness to the detective Loki in Denis Villeneuve’s magical, dark thriller, and much of this has to do with Jake’s acting. He brings his character to life by initially attempting to subdue and suppress a desire to pursue truth and justice by causing perpetrators the same pain their victims endured – only to succumb to these primitive emotions. Loki is a side character in a story about a father desperate to find his kidnapped daughter, but despite great acting by Hugh Jackman and others, it is still Loki I am most curious about long after the credits have rolled.
JAKE GYLLENHAAL’S BEST ACTING PERFORMANCE:
(1) Nightcrawler (2014)
There is something slightly absurd, almost maddening, about the fact that Gyllenhaal did not win an Oscar for his role as Louis Bloom in Dan Gilroy’s magically intense, dark and deeply fascinating character study in which Jake takes on the role of a manic freelance photographer. On the neon-lit nights of Los Angeles, he photographs deadly victims as if they were real estate ads, literally walking over corpses to take the picture, with a conviction and intensity that is just as watchable today as it was a decade ago. Jake is truly raving in this role, for which he has also slimmed down considerably, and he obviously should have won the Golden Boy for this role.