In 2010, Gyllenhaal stared into the mirror, saw a leading man looking back, and blinked—or so the line on him goes. That was the year that he starred in Love & Other Drugs, the romantic comedy in which he played a frequently undressed pharmaceutical rep, and Prince of Persia, a big-budget sword-and-sandals epic adapted from a video-game series. Neither movie fared well critically or commercially, and since then he’s been making what are referred to in Hollywood as “interesting choices,” chasing drug cartels (End of Watch), kidnappers (the disturbing abduction drama Prisoners), car accidents (Nightcrawler), and—in Denis Villeneuve’s strange and dreamy Enemy—himself through films that offered little in the way of box-office glory and plenty of chances to map out darkness. And if that weren’t enough artistic cred, Gyllenhaal also explored theater, starring in two dramas by the British playwright Nick Payne, If There Is I Haven’t Found It Yet and Constellations, his Broadway debut. This account of his turn toward the bleak and unconventional is so much the accepted wisdom that before he collects me at my hotel for dinner, a friend in New York e-mails, “I hope he picks you up in a shitty Kia . . . just the latest in his bold, unexpected Hollywood choices.”