"Sign O' the Times" (1987)
"Sign O' The Times" may be the oddest of Prince's lead singles. The man was at the height of his commercial and critical success, and his previous album Parade – a delirious tour into French jazz-pop that yielded the all-time funk classic "Kiss" and the cinematic debacle in Under the Cherry Moon – had taught his audience that Prince could be wonderfully unpredictable. Yet "Sign O' The Times" sounded like nothing he had done before. The starkly minimalist track found him playing blues guitar over a Fairlight synthesizer, and wailing over the world's troubles. "Man ain't happy truly until a man truly dies," he sings. Engineer Susan Rogers, who worked on the track along with keyboard programmer Todd Harriman, told Billboard, "He was coming down from the headlines of his huge success and he was aware that his audience was changing and things were changing for him. So it may have been a little bit darker in that respect." Peaking on the Billboard Hot 100 at Number Three and topping the Village Voice's Pazz & Jop poll for single of the year, "Sign O' The Times" was an affirmation that Prince's audience would follow him anywhere, no matter where he led them.