Living the Classics:

Prince’s Sign ‘O’ the Times

Words: Asher White
May 1 2022

35 years since Sign ‘O’ The Times, as clunky and complete a statement as we could ever want from Prince.

With our series Living the Classics, WBRU is publishing essays on any album from any artists’ back catalog that a writer believes to be classic—whatever the term may mean. 

Something occasionally overlooked about Prince is that for all his feline grace, he was actually often kind of awkward. As a public figure he was liable to make ill-advised statements and mystifying decisions; his discography, expansive as it is, is rife with clunky, occasionally inexcusable moments. This is, in part, what made him so captivating: not only was he a god, but a somewhat unreliable and perplexing one.

Nowhere is this duality clearer and more exhilarating than on Sign ‘O’ the Times. It would be his 9th album and 8th consecutive (!) masterpiece, riding off of an insane hot streak that had begun with 1979’s Prince and would continue into 1989’s Lovesexy. At 28, he had a triumphant career behind him—crafting perfect by-the-books disco; premiering his own brand of carnal electro-funk; finding outrageous success with the pyrotechnic smash hit Purple Rain before pivoting to artful psychedelia; paring down his signature style into spiky, airtight funk. On Sign ‘O’ the Times, it all began to catch up with him: it’s the drunken walk home, the restless night, and the bleary-eyed morning after; the moment his vacuum-sealed sound threatened to expire.

On the album cover, Prince is framed by and turning away from a display of opulence: lush greenery, fireworks and Las Vegas signage, an enormous drum set, a glowing crystal ball, piles of flowers, the detached front of a car. His iconic, suggestively-shaped guitar, usually a token of his raw sexuality, lies flaccid on the floor, drooping down towards the bottom of the frame. Prince himself is on his way out, exiting his surroundings like a 1980s Angelus Novus. It’s unclear where he’s heading (it would still be a half-decade before he ran to religion and went full monastery-mode—though Sign’s “The Cross” begins to reveal a pathway towards salvation). Most importantly, he is not in focus, clipped at the bottom right corner and blurry: he’s too close to the lens.

The first few listens of Sign ‘O’ The Times can be disorienting—it lacks the concision and drive that makes earlier Prince albums so immediate. Instead, Sign is fraught and disjointed, with a tracklist that mounts tension but doesn’t provide much relief. The titular opening track has occasionally been deemed a “protest song,” but this isn’t quite right—it bluntly references the era’s hot topics (AIDS, drug addiction, gang violence, natural disasters, poverty), but its politics are too ambivalent; its target too unclear. "Times… it's silly, no?” he murmurs. What is he protesting? Time itself?

It’s a weird move, surveying urgent global crises with a disembodied and non-committal sense of disappointment. It’s an even weirder way to open an album. And it’s an even weirder primer for “Play in the Sunshine,” a 5-minute rockabilly bender that includes a proggy dual marimba-guitar solo, a synth-drum/live-drum showdown, and a dizzy half-time choral outro. But this is the drama of Sign ‘O’ The Times: apocalyptic hedonism; uneasy, alienated intimacy; disquieting darkness alongside blindingly bright light. “It,” which presumably should be a cathartic sex jam, is actually remarkably tense, with synth beds more fit for a suspenseful 80s CSI drama than an R&B album. Same goes for “Hot Thing,” which is tortured and aggro even before the metallic buzzsaw synth sears through the chorus. Or “The Cross”, a quasi-doom-metal power ballad to Christ. And what’s going on with the Renn Fair flutes in “Strange Relationship,” a song that had, years prior, been recorded as a jazzy (and maybe superior) piano track?

All of this is not to disparage Sign ‘O’ The Times but rather emphasize its unlikely and vertiginous brilliance. First of all, it contains obvious gems: both “Slow Love” and “Adore” are some of Prince’s greatest love songs; each reach ecstatic highs that can, without warning, make a grocery store checkout line seem unbelievably erotic (and should probably be illegal to listen to in public alltogether). “I Could Never Take the Place of Your Man” is the greatest song ever written. But the album is, fundamentally, a “grower”, in both the micro and macro sense. It grows on the individual listener—spend enough time with it, and it reveals its depth: its odd sequencing begins to sound strategic and indisputable, its murky colors richer, its queasiness suddenly addictive. But in a larger sense, the album has proven its value over time. “Housequake” is a revolutionary synthesis of James Brown and Run DMC; the gender neurosis of “If I Was Your Girlfriend” essentially predicts Andrea Long Chu’s landmark essay “On Liking Women”. And there’s never been a dearth of Prince/Andre 3000 comparisons, but more than any other album, Sign O’ the Times demonstrates the former artist’s profound influence on the rapper: Prince, like Andre 3000, is a deeply eccentric romantic who litters his songs with strange, intimate asides, murmuring questions in the margins of his songs (the essential coyness they share is particularly pronounced on Sign; “The Ballad of Dorothy Parker”’s muted, aquatic funk—as well as its bemused, polyamorous attitude—is a dead-ringer for several Love Below tracks).

Retrospect has cast Sign ‘O’ the Times in a warmer light, and over the years, it’s increasingly been regarded as Prince’s magnum opus. If it is the definitive Prince album, it is so only for its betrayal of a “definitive Prince.” Sign documents the superstar at a moment of incredible uncertainty. Paralyzed by his notorious perfectionism and mired in indecision—it’s technically the wreckage of 3 failed projects—it veers violently between the poles that framed his career: sex vs. love, extravagance vs. sparseness, sin vs. God (eventually God won—it happens to the best of us). Sign’s perilous position between imminent downfall and total transcendence makes it the artist’s most thrilling work. Ultimately, the allure of Prince is suspense: the suspense generated by his pursuit of perfection, by his refusal to be truly vulnerable, by his lingering just out of reach. Up until then, he was sure to come out on top in the end, surefooted and unscatched. But on Sign ‘O’ the Times, the chaos goes deeper, the stakes heightened: for the first time in his career, it seemed like he might not pull it off.






WBRU RADIO (Alternative)

360 (R&B/hip-hop)