Dated: Bob Dylan (1965)
Sedgwick was an icon of many names: “It Girl,” Vogue’s “Youthquaker,” and 1965’s “Girl of the Year.” As Andy Warhol’s muse, Sedgwick was caught in a whirlwind of romances within Warhol’s inner circle in the mid-60s, most famously with singer-songwriter Bob Neuwirth and the legendary Bob Dylan, who apparently ended their short-lived relationship by marrying another woman, Sara Lownds, in a secret ceremony.