Inside Prince's Groundbreaking Double LP 'Sign 'O' the Times'

How the late icon's 1987 masterpiece fused pop, rock and R&B into a sprawling new sound

Delve deep into the making of Prince's 1987 double-LP masterpiece, 'Sign 'O' the Times.'

Sign 'O' the Times is Prince's recorded apex, the summation and greatest articulation of all the musical fusions he'd alchemized up to that point. It's the album where he does it all – combining his synth-drums and meta-funk explorations with psychedelia, rock-guitar heroics and mainstream pop on the order of 1999 and Purple Rain. Reflecting both hip-hop's early cutting edge and his own restless muse, with new twists on old themes, Sign 'O' the Times was at once more confident, rangy and visionary than its predecessors. It took Prince's beat-centered, future-forward songcraft not just to the next level but to multiple levels.

Tellingly, the album is a distillation of many projects that exploded from Prince's imagination during the most creative year of his life. The first was Dream Factory, an aborted double album begun with the Revolution in December 1985, just as they were wrapping up Parade. That same month, he wrote a song for Miles Davis ("Can I Play With U?") and recorded an album's worth of jazzy-funk jam sessions – with Sheila E., her bandmate Levi Seacer Jr. and Eric Leeds – that were slated for an instrumental LP, The Flesh, which was also eventually shelved. "On any given night he might just gather us and we'd go in and just play," says Leeds. "He would always say, 'Maybe I'll put this stuff out.'"

In March 1986, Prince inaugurated his new state-of-the-art home studio in Chanhassen, Minnesota, with "The Ballad of Dorothy Parker," an avant-garde slow jam with stuttering electro beats and vocals that flash like fractals, with different effects and voice tones, as Prince plays the roles of both Ms. Parker and himself, singing a bit of Joni Mitchell's "Help Me" and even voicing the ring of a telephone. "Prince had this dream where he thought of this song – the dream of the bathtub and all that – and he came downstairs and told me, 'Let's go. Let's record,'" says Susan Rogers, Prince's staff engineer and production right hand on Sign 'O' the Times. "The console hadn't been tested yet, so while we were doing 'Dorothy Parker' I'm thinking, 'God, this is awful,' because there was no high end. But I couldn't test it because he was working. Typical of Prince, our session lasted roughly 24 hours. We didn't get out of there until the next day. And he was totally happy. The seed of the song came in a dream anyway, so he used that artistically – he just let the whole thing be kind of muffled."

Prince then recorded "Starfish and Coffee," a song built around piano, co-written (and co-sung) with his fiancée, Susannah Melvoin, and a number of other tracks. By April, he had an 11-track version of Dream Factory assembled on a cassette, and he was even toying with the title as a new name for the Revolution. That month, he had the Number One song in the country, "Kiss," and the Number Two, the Bangles' version of his "Manic Monday." Touring Europe that summer, Prince was writing at such a clip, he recorded new songs during a Paris soundcheck jam and show. This was the genesis of Sign 'O' the Times' solo-heavy, brass-plated funk jam "It's Gonna Be a Beautiful Night," though Sheila E.'s "Transmississippi Rap," recorded over the phone, was added later. There was even talk about creating a Dream Factory musical; Prince was working on a script.

By July, Dream Factory had swelled to 18 songs, including two startling new tracks. Programmed drums and sampling were transforming pop's sound: 1985 had been the year of Run-DMC's King of Rock, as well as Mantronix, Double Dee and Steinski, and the birth of dancehall reggae, via Wayne Smith's "Under Mi Sleng Teng." "Sign 'O' the Times," recorded in a 10-hour sprint, was a topical jam built around a fat bass line, wicked funk-guitar outbursts and beats that remade the new minimalism in Prince's
 image, leaping off "Kiss" into darker 
territory. "The Cross" was a psychedel
ic meditation on the Christian symbol
 and the Second Coming of Jesus, with
 layered guitars and sitar colors that re-called George Harrison's spiritual pop.
 Recorded entirely solo on a Sunday at
 Sunset Sound in Los Angeles, it was an
other example of Prince finding inspira
tion in imperfection. "[The drumming] 
speeds up, but he wasn't using a metronome. ... I thought he was actually going 
to scrap it," Rogers recalls. "But he was 
happy with it."

All this solo recording was a sign,
 and the decision to formally disband
 the Revolution came that fall. Keyboardist Lisa Coleman and 
guitarist Wendy Melvoin had already raised the possibility of leaving, for reasons that included Prince's relationship with Wendy's twin sister, Susannah, which was
 growing rocky. Eventually the duo were dismissed, along with drummer Bobby Z, who would be replaced by Sheila E., looking to swap her newly minted pop career for a chance to demonstrate her A-list musicianship; only Revolution keyboardist Matt Fink remained.

Though completed, Dream Factory was scrapped by Prince, who wanted to make a clean musical break. With the loss of his longtime friends and musicians, Prince doubled down on his workaholism. He cut new songs at his home studio, among them "Hot Thing," a dizzying bit of electro-funk featuring blasts from saxophonist Eric Leeds. He began work on a new film project (never finished) titled The Dawn. He reworked an old song, "Wouldn't You Love to Love Me," for Michael Jackson, after rejecting his rival's invitation to duet with him on "Bad." He cut material for country-pop acts, including Dolly Parton and Deborah Allen, and even a song for his beloved Joni Mitchell, "Emotional Pump" (she passed, as did Jackson and Parton).

The next breakthrough was "Housequake," a twisted, hard-funk party jam with Prince's pitched-up vocals, which he started recording the day after the public announcement of the Revolution's breakup. As a statement of updated direction, announcing a "brand-new groove," its cyber-stepping James Brown get-down could hardly have been clearer. That song's altered vocals, meanwhile, fueled another idea: a female alter ego said to be inspired by 19th-century intersexed memoirist Herculine Barbin, whose nickname was Camille. Prince decided "Camille" should have her own LP. So he blasted out five songs in under two weeks, and by November the completed record had been test-pressed. It featured another stunning song, "If I Was Your Girlfriend," a gender-jumping slow-jam head trip that longed for deeper connection with a lover. It was hard not to read it as a letter to Susannah Melvoin. Naturally, Prince began conceiving a Camille film project too.

Eventually, these ideas, too, were shelved, and Prince decided he would release a three-LP, 22-track magnum opus titled Crystal Ball, which drew on all the material he'd been creating. Warner Bros. was worried about overwhelming the market with such an expensive set, however, especially in light of the performance of his past few projects. "It was one of those rare meetings where the label executives actually came to the studio," recalls Rogers, who was working with Prince at Sunset Sound. He was eventually forced to pare the album down to a double LP. "He was upset about it," Rogers says. "Then he accepted it and we moved on."

For all his creative wildness, Prince was equally driven to succeed in the marketplace; for him, these ambitions were not incompatible. One of the final songs recorded for Crystal Ball was "Adore," a song targeted toward R&B radio with dazzling falsetto works and gorgeous horn arrangements. With its image of angels raining tears over the beauty of two lovers, it stands as perhaps Prince's supreme love song. Plucked from his vault, the 1982 recording of "I Could Never Take the Place of Your Man" was updated and put on the roster, adding a pop-rock song in the style of "1999," complete with an extended jam at the end. "U Got the Look" was a New Wave pop trifle with jagged synths and fierce guitar noise, featuring vocals by Sheena Easton, who just happened to be passing through the studio in L.A. when Prince was recording it.

The double LP, now titled Sign 'O' the Times, was stitched together carefully at Sunset Sound and finished in January 1987. "Sequencing a record with him was really extraordinary," Rogers says. "He put so much value in the sequence. Each side was like an act in a play: It had to have a beginning, middle and an end. Great artists understand that a work of art should give you a sense of momentum when you first encounter it, and a sense of momentum when you walk away from it."

The upshot was a record packed so full of groundbreaking ideas, reflecting both the mainstream moment and Prince's restless muse, that it was hard for some to wrap their heads around. "What people were saying about Sign 'O' the Times was, 'There are some great songs on it, and there are some experiments on it,'" Prince told Rolling Stone in 1990. "I hate the word 'experiment' – it sounds like something you didn't finish. Well, they have to understand that's the way to have a double record and make it interesting." It's more than interesting – it's a pop-art landmark.

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