Sign O' The Times: how Prince created a masterpiece – and ruined his career

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Released in March 1987, Sign O’ The Times emerged from this creative eruption as a sprawling 16-song masterpiece. It is widely regarded as one of the best albums of the 1980s and the closest Prince got to his own White Album. From the bleak and socially conscious state-of-the-nation title track – which referenced drug addiction, gang warfare and a nuclear apocalypse – to the raucous funk of Housequake and the all-out pop of U Got the Look, the album was kaleidoscopic and off-kilter in equal measure. Sign O’ The Times, which is about to be re-released as an even more sprawling box set, wowed the critics and remains adored by Prince fans. This week, Rolling Stone named it as one of the top 50 albums of all time.

Yet this extraordinary compendium from Prince’s purple patch marked the beginning of the end of his imperial phase. For all its greatness, Sign O’ The Times didn’t perform as well as his previous three albums: Parade, Around the World in a Day and Purple Rain. Further, the emergence of hip hop into the mainstream pop charts, a bitter falling out with his label Warner Bros and Prince’s seeming inability to exercise quality control over his future output saw the pop star’s popularity start to wane. In 1993 he changed his name to a symbol. Although he still had hit albums and remained one of the most electrifying live performers in the world until his death in 2016, Prince would no longer be seen as the megastar he once was.

“Sign O’ The Times came from a place of chaos, both creative and professional,” says Michael Pagnotta, who was Prince’s publicist from 1991 to 1995. “It went Platinum [selling a million copies in the US] after four months and the singles did nicely. But it was not Purple Rain. And that failure to follow up to his own standard was something that haunted him for the next several years at least.”

Problems had been brewing for a while. Prince was a tricky boss to The Revolution, and his on-stage outburst in Yokohama was not a surprise to some of his bandmates. A notorious perfectionist, Prince would fine members for minor indiscretions, such as drinking beer backstage. Key members Wendy Melvoin and Lisa Coleman nearly quit before the Parade tour while other Revolution members thought the band had become too large and unwieldy. One of the new members was Melvoin’s twin sister Susannah, to whom Prince was engaged and about whom he’s thought to have written Nothing Compares 2 U.

All the tensions caused a frosty atmosphere and led to black moods in Prince, who officially disbanded the group in October 1986. The singer was also bruised by a high profile commercial failure. Under The Cherry Moon, a film that tied in with the Parade album, had bombed. In addition he was preoccupied with putting the finishing touches to his costly Paisley Park Studio complex in his native Minnesota and was, as of 1985, a label executive having launched Paisley Park Records. In other words, he had a lot on his plate. The man was obsessed with his music (a Spitting Image sketch once showed a microphone stand bursting into Prince's bedroom to find him in bed with another microphone stand) and he thought that a fresh start from The Revolution would give him latitude for a creative rebirth.

His plan worked almost too well. Once back from Japan he hit the studio hard (he also split from Susannah, just to add to his woes). His first project, soon abandoned as he was in the process of firing them, was a double album that The Revolution had all but finished called Dream Factory. Given the circumstances it was unreleasable. The second project was an album known as Camille. Camille was a Prince alter ego: an androgynous character who sang in a high falsetto voice. His plan was to release an album under the name without mentioning his involvement. He recorded it and early copies were pressed but the singer, perhaps under pressure from nervous execs at Warners, pulled the plug weeks before its intended release. Prince’s third project involved combining the two: taking the best of the Dream Factory material and the best of Camille and adding a batch of new songs. He would release it as a triple album called Crystal Ball. Prince recorded numerous new tracks with titles such as Shockadelica and Rockhard in a Funky Place. However Warners slammed on the brakes. A triple album was too risky, particularly after Under The Cherry Moon tanked. So the label reached a compromise agreement with Prince: cut it down to a double album and we’ll release it. He ditched seven tracks, added a duet with Sheena Easton (U Got the Look), and called it Sign O’ The Times.

At last, a tangible product had emerged from this creative cluster bomb. “The closest comparison I can make is [The Beach Boys’] Brian Wilson and the Smile project,” says Pagnotta. “Wilson’s coming out of Pet Sounds and Smile obliterates him as a human being and an artist.