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.