Montgomery Clift had the most earnest of faces: big, pleading eyes, a set jaw, and a side part that reminds you of old pictures of your granddad. Onscreen and off, he was what the kids these days would call “an emo” and the least generous of your friends would call a “sad sack.” If he lived in the ‘90s, he would have been king of the heartfelt mixtape. Clift played the desperate, the drunken, and the deceived, and along with Brando and Dean, heralded a new direction in cinematic masculinity. But a car crash in the prime of his career left him in constant pain, and he drank himself to an early death. The trajectory of his life was as tragic as any of his films. But for 12 years, he set Hollywood aflame.