Not many performers have had as strange and impressive a career as Jake Gyllenhaal. In fact, his first three “big” movies are kind of a thesis for his trajectory: a sensitive, classical turn in the endearing October Sky; an unnerving, odd performance in the obtuse and dark thriller Donnie Darko; and going full-on goofball for the silly comedy Bubble Boy. These three films show both Gyllenhaal’s versatility and his willingness to give every film his all, no matter how frivolous it may seem. His career spans from blockbusters (The Day After Tomorrow) to serious dramas (Brothers) to dramedies (Love & Other Drugs), and no matter the genre, Gyllenhaal always turns in something interesting.

So in anticipation of Gyllenhaal’s latest film, Life, I’ve opted to look back and cherry pick the actors’ five best performances. And know this: I seriously considered putting Bubble Boy on here.

5. 'Donnie Darko'

This is the film that kind of put Gyllenhaal on the map as an actor who could do more than deliver a solid performance in a nice film like October Sky. Filmmaker Richard Kelly’s twisted, ultimately befuddling sci-fi pic is an absolute trip, but Gyllenhaal sells it with everything that he’s got. The movie doesn’t work at all without Gyllenhaal anchoring this thing from a character perspective, and the nuanced darkness of the performance was absolutely a sign of even greater things to come.

4. 'Enemy'

Two Gyllenhaals for the price of one! Filmmaker Denis Villeneuve’s head-trippy follow-up to Prisoners is a divisive film to be sure, but I’m firmly on the “loved it” side. Enemy finds Gyllenhaal filling the role of a college professor who discovers that he has a doppelganger, leading him to question pretty much everything about his life. Beyond Villeneuve’s masterfully manipulative direction, Gyllenhaal delivers a pair of spectacular performances here that are just different enough to buy that you’re (maybe) watching two different people onscreen. It was a tall order to be sure, especially since the narrative doesn’t do much hand-holding for the audience, but Gyllenhaal knocks it out of the park and then some. And that final scene!

3. 'Brokeback Mountain'

Gyllenhaal also has the distinction of starring in one of the great love stories of our time. It’s weird to think that just over 10 years ago Brokeback Mountain was this whole “controversial” thing where Gyllenhaal and Heath Ledger were oddly lauded for their “bravery.” The actors didn’t see it that way—they were simply bringing an intimate, tragic love story to life, and they did so in an absolutely terrific manner. Ledger towers over this thing, but Gyllenhaal holds his own in the much more openly expressive role of Jack, and the film would serve as another stepping stone for Gyllenhaal to bring his complex talent to bigger studio fare.

2. 'Zodiac'

Gyllenhaal’s frustrations with director David Fincher during the filming of Zodiac are well documented, but ultimately the actor came to acknowledge that the process was all in service of making a great film. And indeed, Zodiac is a flat-out masterpiece that also makes impeccable use of Gyllenhaal’s strengths. He brings a curious sensitivity to the character of Robert Graysmith, but Fincher also brings out Gyllenhaal’s knack for comedy in surprising ways—Zodiac is dark as all get-out, but it’s also hilarious when it wants to be. The obsession that haunts Graysmith isn’t easy to carry across the film’s extended timespan, but Gyllenhaal sells it tremendously, culminating in one of the great anti-climactic climaxes in cinema history.

1. 'Nightcrawler'

But Gyllenhaal’s best performance so far is even more proof that the guy is one of the most interesting actors working today. Gyllenhaal carries 2014’s dark thriller Nightcrawler with aplomb, appearing in nearly every scene. It’s a haunting performance that absolutely earns comparisons to Travis Bickle, as Gyllenhaal’s gaunt frame and plain appearance telegraph this character’s obsessive drive right from the get-go. Through all of his despicable actions, Gyllenhaal still manages to make Louis Bloom human and compelling—on some level you kind of want to see the guy succeed, even as he is devoid of any sense of decency or respect for life. The film itself is brilliant, and now serves as one of two masterful performances from Gyllenhaal. But the versatility of his career, ambition of character, and passion for cinema and performance promise that there are plenty more great performances to come.