A new collection reveals Prince’s artistic scope at the height of his powers

It’s hard to imagine now, but when Prince’s Sign O’ The Times hit record stores in the spring of 1987, it was widely viewed as a comeback record. The 1982 double album 1999 had converted the critics’ darling into a certified hit-maker; and 1984’s Purple Rain LP and film turned Prince into a superstar. But 1985’s Around The World In A Day and 1986’s Parade—while producing unassailable singles like “Raspberry Beret” and “Pop Life” (World) and “Kiss” (Parade)—drew mixed reviews and were relatively disappointing commercially.

Then along came Sign O’ The Times: two discs’ worth of hard funk, giddy pop, and wild experiments, even more expansive and adventurous than 1999. The album produced three Billboard Top 10 hits: “U Got The Look,” “I Could Never Take The Place Of Your Man,” and the title track. It also dominated the critics’ best-of-the-year lists. During rare one-on-one encounters with the media during his mid-1980s rise to fame, Prince would often indicate that he was working on music constantly in his home studio, and had entire albums sitting in “the Vault” that had been completed but never released. The eclectic, electrifying Sign O’ The Times sounded like a greatest-hits collection drawn from all that unreleased music.

What wasn’t widely reported at the time—but later became a major part of Prince lore—was that Sign O’ The Times was actually something of a salvage job. In a way, it was a “best of the never-heard” set, drawing elements from three different aborted projects: a sophisticated, romantic and jazzy album titled Dream Factory, a raw and eccentric dance record titled Camille, and a triple-disc blowout titled Crystal Ball. The latter was meant to be a defiant “I’m not washed up yet!” rebuke to all the critics who’d shrugged off Prince’s previous two LPs, as well as his flop 1986 movie, Under The Cherry Moon.

When the Prince estate and Warner Bros. announced they were reissuing Sign O’ The Times in an expanded “Super Deluxe” edition (out this Friday, September 25, but available for pre-order now), many fans hoped the set’s curators might rebuild these never-released records, each of which have been passed around in makeshift forms on bootlegs for years. But here’s the bad news: Not only does this Sign O’ The Times edition not feature track-by-track recreations of Dream Factory or any of the rest, it also omits songs from those projects that have surfaced elsewhere. If you want to hear “Dream Factory” itself, or the ten-minute version of “Crystal Ball,” you’ll have to dig out your copy of Prince’s 1998 album Crystal Ball (which, confusingly, is not the same as the album Warners rejected). Ultimately, this eight-LP set (which in its physical form also contains a DVD of a full concert performance) isn’t concerned with what-might’ve-beens. It’s more about making Prince’s ambitious, magnificent masterpiece even grander.

It does this by including over a dozen songs that never appeared on any of the nascent versions of Sign O’ The Times. While much of the material earmarked for Camille and Crystal Ball was released commercially in Prince’s lifetime, a healthy chunk of Dream Factory hasn’t been widely heard outside of bootlegs. And even people who’ve illegally downloaded bootlegs of Dream Factory—a record that went through several iterations before it was scrapped altogether—never got a copy that included some of these new songs, like the bouncy ’70s-style AM pop ditty “Everybody Want What They Don’t Got” or the sweetly swinging ballad “Adonis And Bathsheba.” Both of them have a playfulness and grace that exemplify what that album was aiming to be.

Prince never talked much to the press about his intentions, so we mostly have to rely on his collaborators’ memories to piece together his original plans for this project—and why he scotched them. Wendy Melvoin and Lisa Coleman of his backing band The Revolution have described the Dream Factory sessions as Prince’s attempt at a truly collaborative record, with the two women in particular providing not just musical support but also lyrics, melodies, arrangements and lead vocals. Prince—the largely self-taught son of jazz musicians, and a devotee of Joni Mitchell—began to incorporate more horns, aiming for a big-band/cabaret sound similar to what Mitchell played with on albums like Don Juan’s Reckless Daughter. He wanted something with scope.

Some elements of this new direction had been evident on Parade, which (as the semi-soundtrack to Under The Cherry Moon) at times evokes the feel of mid-20th century Europe, when a wave of Black entertainers took up residence in ritzy nightclubs. That same general approach is also apparent in Prince’s often under-appreciated ’90s work, where he became more of an old-fashioned bandleader, delegating solos and riffs to his hot combo rather than doing all the flashy stuff himself. But the Dream Factory era songs are looser and kookier, with more of a sense of joyous discovery. It has a lot of that sui generis Prince weirdness, in which he sometimes seemed to indulge just to crack himself up—like when he’d utter surprise interjections in odd voices, as though imitating a room full of people at a party.

According to a lot of sources (including Michaelangelo Matos’ excellent 33⅓ book on Sign O’ The Times), Prince went through three configurations of Dream Factory between April and July of 1986. The first was a single album, full of some of the most enjoyably frivolous songs he and The Revolution had ever cooked up—including a few of the more unusual ones that ended up on Sign O’ The Times, like the discursive and unclassifiable “The Ballad Of Dorothy Parker” and the thumping, oddly personal “Strange Relationship.” But perhaps because Around The World In A Day and Parade had been dinged for their more undernourished qualities, Prince and The Revolution kept recording, looking to capture the full range of styles and ideas they’d been talking about since the project began.

Two months later, they had a double-album version of Dream Factory, ending with the wonderfully nutty “All My Dreams,” which sounds like a fevered rendition of a corny 1930s movie musical, performed by the cast of Sesame Street. One month after that, Prince reshaped Dream Factory yet again—into another delightfully offbeat and off-the cuff double-disc set, adding a handful of future Sign O’ The Times classics, like the title track and the ironically cheery “I Could Never Take The Place Of Your Man.” If this had been the record Prince released, it likely would’ve been just as beloved as Sign O’ The Times.

But two things happened before the artist could pull the trigger. The most important development was that Prince had a falling-out with The Revolution, for reasons even the band members have never been able to explain fully. Coleman and Melvoin have speculated that Prince decided collaboration didn’t suit his self-image. Others have said that some of Prince’s longtime cohorts (including Wendy and Lisa) irritated him by complaining about some of the new musicians he was bringing into the studio. Whatever the reason, Prince suddenly soured on Dream Factory, even though Warner Bros. was reportedly ready to release that third version of the album.

Prince retreated to his studio and went back to working as more of a one-man-band, experimenting with recording technology that made his vocals sound high and alien. He dubbed this new voice “Camille,” and recorded several sparse, rhythmic, and heavily synthesized songs in this style, include a new version of “Strange Relationship” and two more songs that ended up on Sign O’ The Times: the sinewy, sexually slippery “If I Was Your Girlfriend” and the hilarious, hard-edged house-party jam “Housequake.” Camille—which Prince wanted to release without fanfare, credited to “Camille”—was also close to being released in 1986. But it never hit stores, and the reasons why (like nearly everything else in Prince’s biography) are disputed. Either Warner Bros. didn’t want to put out an anonymous Prince album, or Prince himself began to doubt the spiritual righteousness of this arcane music.

Either way, he rallied immediately, returning to the idea of going big. The triple-album Crystal Ball—the one Warner Bros. nixed—would’ve contained most of the final version of Dream Factory and most of Camille, with the former’s songs re-arranged and re-recorded to de-emphasize The Revolution’s contributions. Crystal Ball added a few new songs too, including several eventual Sign O’ The Times favorites: the peppy “Play In The Sunshine,” raunchy “Hot Thing,” low-key country-soul sketch “Forever In My Life,” and an extended live performance of the glorious free-for-all “It’s Gonna Be A Beautiful Night.” It’s hard to say how Crystal Ball would’ve been received, had Warner Bros. not balked at the length. Prince certainly never forgot the slight, adding it to the long list of grievances that would later lead to him puckishly changing his name to an unpronounceable symbol.

Yet in his 33⅓ book, Matos argues that no matter what Prince intended, Sign O’ The Times was exactly the album he had to release in 1987. Matos notes that it arrived in a year when the charts were filling up with Prince imitators, and reminded critics and music buffs that no one could make hooky, soulful, beat-driven pop-rock that sounded anywhere near so inspired or idiosyncratic. Matos also suggests that by renaming the album after its only overtly political song—an unflinching “state of the union,” in the spirit of Marvin Gaye—Prince joined the rising tide of pop stars who’d begun commenting on social injustice at the end of the Reagan era, making him seem all the more on-point. (“Sign O’ The Times” remains one of his most popular songs, perhaps because rock’s old guard appreciate that it sounds like protest music.)

Even after listening to six discs’ worth of songs that were under consideration for this album, the original two-LP Sign O’ The Times still seems like the best way Prince could’ve refined and packaged this material. The track order is perfect, flowing easily from Top 40 fodder to avant-garde funk to some of the most free-flowing eruptions of Prince’s subconscious ever committed to tape. (Nobody but Prince could’ve come up with a song as elusively magical as “The Ballad Of Dorothy Parker,” which sounds like something he just started humming to himself while fiddling around with a new synthesizer.)

It might’ve been better if this set’s generous collection of outtakes were arranged into a more logical order, to tell the story of these sessions more coherently. Nevertheless, the Super Deluxe Sign O’ The Times does help explain where this music came from, and why it feels more fleshed-out and urgent than much of what Prince released post-Purple Rain. He went on a journey with these songs, released and unreleased.

Like Neil Young, Stevie Wonder, Brian Wilson, and many of pop music’s other legendary studio rats, Prince conditioned himself to converse through song, turning whatever was going through his head on any given day into music… and then recording it right away, while the feeling was fresh. The Sign O’ The Times special edition contains fully arranged, performed, and produced songs—thrilling ones, too, like the ecstatic call-and-response jumper “When The Dawn Of The Morning Comes”—that Prince stuck in his vaunted Vault and never revisited. He tossed releasable music aside, knowing he could make more.

Still, when you compare what Prince workshopped versus what he actually sent out into the world, it becomes clear that he rarely released any music unless he felt it was saying something: about his own beliefs, about human nature, or even just about what music itself could do. Prince thought very deeply about what he wanted his albums to be. In 1987, one popular take on Sign O’ The Times was that it was all about Prince proving himself again: to the fans, to the press, and to his fellow pop stars. But these songs may have meant even more to the person who recorded them. This was Prince the explorer, reaching far and wide—on the hunt for the kind of sounds even Prince had never heard before.