Prince’s Sign o’ the Times Turns 30: The Tumultuous Making of a Masterpiece

Tracing the many false starts and detours that led to one of Prince's greatest achievements

Dusting ‘Em Off is a rotating, free-form feature that revisits a classic album, film, or moment in pop-culture history. This week, Blake Goble traces the long and tumultuous path that led to Sign o’ the Times.

Goodness, where to even begin with this chef-d’oeuvre of blistering soul, funk, pop, hip-hop, and socially inclined yet seriously sexy music?

Words can never take the place of the man, Prince, but we will try. Sign o’ the Times is Prince at his most complete, under control yet completely out of it, doubling down with his most notable batch of music to this point. If ever an album illustrated the diversity and gifts of Prince, this is it. But to understand and appreciate Sign o’ the Times, one must look at every ingredient accrued over a long and difficult period of time in Prince’s career.

This was an album made through distress and alternate directions, and its production gives off the sense that Prince might not have been clearheaded about its development. At least not in any linear sense. Prince had parts and ideas everywhere, vying for a place on the album, and only the strongest bits survived. In short: Times is Frankenstein’s monster — were the monster fabulously funky and more inclined to get down. Well, maybe get a little nasty too…

By all accounts, this was a disorganized, even troubled production. And yet, the final release is recognized as one the bedrock greats of ’87: eclectic, erotic, and even a little ecclesiastical. But before we can play in the sunshine, we gotta sift through the purple dirt.

Exactly how many false starts did it take for Prince to get this album to where he wanted it? Apologies for the Charlie Kelly-esque timeline work to follow, but tracking the Sign is a bit tricky.

Artistically, breaking down this album is like trying to list off and evaluate every piece of design in a European chapel. It’s all a work of art. Or better yet, it’s like the Jackson Pollack of Prince albums. Just try picking your favorite line of color. And if you remove one strand, you risk collapsing the whole fragile, elephantine effort. But here’s the thing, critiquing Sign for its merit is really just complimenting. It has copious amounts of classic singles, and it stands as a testament to Prince’s musical diversity. Breaking Sign down for its history is a whole ‘nother thing. A hunt for Prince’s state of mind.

In 1986, Prince directed his first feature film, Under the Cherry Moon, and while the black-and-white gigolo jaunt was a commercial flop, it resulted in a fabulous soundtrack album, Parade. But alas, the album that brought us “Kiss” and Christopher Tracy was not the hit Warner was hoping for. Prince may have been burning a bridge without knowing it. Painting the legend of Prince as control-master, he’d managed to get the original director of Cherry Moon removed from the film so he could make his debut behind the camera. Tensions between Prince and his band, The Revolution, were at an all-time high. Prince wanted what Prince wanted, and damn it, it was going to be BY PRINCE. The Artist was experiencing growth and change, but it was of a singular nature. Purple Rain made the man a household name, and with that came the demanding sense of self. What came before Sign o’ the Times wasn’t so much an artist being a nightmare or a dictator, but perhaps one struggling to define and defend himself.

It’s a pain to track Prince through this period, but that’s mercurial uncertainty for you. Prince took a million next steps, with several undone or failed project ideas.

As former Prince tour manager Alan Leeds put it, “Concepts for albums were coming to him almost as quickly as the songs were.” Welcome to Prince’s Dream Factory. Prince started configuring Dream Factory over several months in 1986, and it would have been his fourth project with The Revolution. “Teacher, Teacher”, “I Could Never Take the Place of Your Man”, and “Strange Relationship” were some of the earliest tracks that would have been included, and those date back to summer 1982. The title track, “Dream Factory”, was recorded in December of ’85 (but would be shelved until Crystal Ball in 1998). Additional developments in the Dream Factory sessions: jazzy love with “The Ballad of Dorothy Parker”, the ultra-catchy, quirky “Starfish and Coffee”, the slamming sex jam “It”. Many of them came back for Sign. Some songs went in the vault. And others would show up scattershot in later projects. In July of ’86, the breathtaking rock gospel “The Cross”, the eventual lead song “Sign o’ the Times”, and “I Could Never Take the Place of Your Man” were laid down. What was Prince’s thesis? Well, Dorothy Parker was a famed 19th century wit, but it was about a waitress. And “It” was a five-minute euphemism, and “Starfish and Coffee” was just a classically Prince inside joke. Come to think of it, Dream Factory was all over the place. But it was called Dream Factory, and anything can happen in dreams, right?

Then Prince took a hit in July. The details of The Revolution’s breakup went tabloid. New members. Shifting lineups. Jealousies. Firings. Individual members’ ambitions beyond the great Purple. Maybe it was life finally imitating art imitating life – millions saw the band catch shit from Prince in Purple Rain, which drew from real drama. It started with Wendy Melvoin and Lisa Coleman being dropped from the band. Or maybe fired. It’s not perfectly clear. The Revolution’s end was nigh. There were rumors of a Prince/Wendy/Lisa project, but that never came to fruition. There was much gossip, but by mid-1986, Prince had shifted gears.

Dream Factory was shut down. The Revolution was over. Now say hello to Prince’s new pet project: Camille.

Camille was a self-titled project for a new singer he was developing named Camille. Also, it should be noted that the androgynous Camille wasn’t real. Camille was a pseudonym for Prince, with his falsetto artificially raised to sound like a woman’s. It was a fascinating new direction, one of those forgotten music stories that’s too Prince to not be true. The Artist went into the studio with engineer Susan Rogers in mid ’86 and started tinkering with a pitch-shifter. He also recorded his voice at a slower tempo, then sped up the sound. (For an example of this sound, consider the shriek of “Erotic City”.)

The Camille concept gained momentum. Sign songs like “Housequake”, “Strange Relationship”, and “If I Was Your Girlfriend” were developed as part of the proposed eight-track LP. If Prince could keep the secret, which was the plan, then Camille could have been an artificial queen. (Bowie, ever the feminine icon, still never fully ventured into pretending he was explicitly a woman; Prince could have made huge waves with this conceit.) Then, as Camille reached mastering in November of 1986, the album died. Prince left Camille. The reasons for this are uncertain at best, but Prince moved on. Some speculated that Prince felt the pressure of being on his own sans a Revolution, and Camille could have been a safeguard. Others think Prince feared Camille’s lack of commercial security.

Now we look into Prince’s Crystal Ball. Before there was the three-disc double album in 1998 that’s canonically the Crystal Ball, there was the 1986 Crystal Ball, an unreleased triple LP. Same name, different uses. Another way to think of it: Crystal Ball was the director’s cut of Sign o’ the Times. (Again, the directional shifts and dramas are hard to track from ’85 to ’87, but lord, the ceaseless output.) This was going to be the one. A stew of leftovers made into something special. Prince amassed 22 tracks – seven from Camille, nine from Dream Factory, and a few new songs special to Ball. The rollicking “Play in the Sunshine”, the spirited and sexy “Adore” (then known as “Adore (until the end of time)”), and the epic funk jam “It’s Gonna Be a Beautiful Night” were new highlights. Prince tinkered with the run order, kept playing with the Camille persona for certain songs, and continued to expand the universe in the studio.

Crystal Ball was an epic, a tour-de-force that swirled with every ounce of Prince’s personality and musical inclination. Funk and rock and god and sex, it could have been the total Prince piece. He sent Crystal Ball to Warner in November ’86.

In the end, Warner Bros. Records balked at the girth of Prince’s proposed LP. Given the commercial stagnation of Parade, and perhaps reaching a boiling point over Prince’s flighty yet fervent demeanor, Warner demanded cuts. Three discs was too much. Prince pushed back, asserting that this was simply the album he was going to release. But Warner countered in a million ways. It was too expensive a proposition. Prince put out too much music and confused listeners. Crystal Ball was for diehards only. As Prince himself put it in 1996: “Because people at Warner were tired, they came up with reasons why I should be tired, too.”

Prince, in a rare moment, compromised. The project ran until the end of ’86, and “U Got the Look” was added just before the new year. Thank you, Sheena Easton. Several tracks were cut, and “Sign o’ the Times” was made the first single, as well as the newly assembled double LP’s album’s title. Finished in January of 1987 and released on March 30th after all those strange starts and missed directions that suggested a crazed, maybe even out-of-control artist in ruin, Sign o’ the Times was hailed as an instant classic. Genius. Prince’s hottest thing.

It went platinum by July, spent 108 weeks on the Billboard Pop charts, and the album went on to be nominated for Album of the Year at the Grammys (losing to The Joshua Tree). A concert film for the album was rushed into production and released by Warner Bros. and Cineplex-Odeon in November of 1987. Naturally, Prince directed it. (Warner, please, Blu-Ray that already.)

The album signaled a new stage of greatness for Prince, and critics and fans adored the cacophonous beauty of it all. Chicago Reader nailed the album’s total control and equal lack of control as Prince mastered hodgepodge. In The Village Voice, the album received an A+ and was voted #1 in that year’s Pazz & Jop, beating out Tunnel of Love and The Joshua Tree in a landslide. Just last year, Pitchfork asserted that finding a track supreme is impossible.

And that’s just the thing. That’s the not-so-subtle secret of Sign o’ the Times. It throws so much good shit out there. It was and still is loved as a full representation of Prince, and the artistic madness in the studio is key to approaching its wild array of sounds.

Marvel at the non-obvious connections. “Sign o’ the Times” is like the inverse of “Let’s Go Crazy”. A sullen, world-weary Prince sings of gang violence, drugs, and AIDS atop a single synthesizer riff with bass sounds. It’s stark, dramatic, world-weary, and a hell of a new direction. Is this album going to be Prince’s societal psalm? Hardly. From the low comes the high of the giddy “Play in the Sunshine”, as Prince sings of sun and kisses and loving your enemies. Maybe life’s not so grim, or it’s worth the fight, or you know what? It’s just the most enthusiastic thing and counters the title track’s gloom with wit and optimism.

And the hits just keep coming. “Housequake” is a thumping party, and Prince, while potentially more evolved and globally minded, still knows how to have a good time. Each song feels like a strong next step – logical or illogical, the music’s always dramatic, and Prince surprises with great success every couple of minutes. It’s impossible to find a bad track. “Dorothy Parker” isn’t about the writer. Prince just liked the sound of the name and opted to tell a jazzy story. But the key is that it wasn’t only inside jokes and references for Prince. The album sounds like great rock and roll.

This LP has everything. Minimalist and maximal sounds. Lyrically heavy tracks with a touch of current events. Non-embarrassing, constantly invigorating funk and groove music. Music for sexy times, too.

Even the album cover – a blue, busted-down Pontiac Grand Prix stopped in front of a messy boulevard of Busby Berkley-like signs, surrounded by drums, flora, lights, the Prince guitar, and a cheeky crystal ball — slyly hints at Prince knowing that out of wreckage arrived a great. Prince is out of focus in the foreground, forcing attention to the mess behind him. It has the rococo determination and over-detailed eminence of the Sgt. Peppers cover.

Thirty years on, Sign o’ the Times is still like a treasure chest. Prince plundered only the best ideas from a moment of creative tumult and worry and came out with something whole, unique, and truly special. The album is all over the place with its messages, and that’s because its development was chaos as creation. Trial and error. The world’s best smattering of leftovers from other works. Some thought it might be the worst of times. Many would argue the best. But in the end, Prince made damn sure folks knew it was the sign o’ the times.

His times.

It’s silly, no?


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