After I wrote about Parade, I had friends who each claimed a different side of that album as their favorite Prince side. I have enough trouble picking a single Prince album as my favorite, never mind an individual side—but now I’m wondering what my answer will be after I make it through the next twenty or so albums. While I reserve the right to chance my mind, today it is hard to argue with Side One of Sign O’ The Times.

Released exactly one year after Parade, this double album went through several different incarnations before emerging in its final, glorious form.¹ I should confess at the start that I have always had a soft spot for a sprawling double album; I prefer Exile on Main Street, for example, over some of the more-focused Stones albums from their peak period, and glory in the overstuffed world of The White Album. Most double albums usually inspire debate about what songs could have been cut out, to make an even better single album, but the tracks I might choose to delete are probably not the same ones other fans would get rid of, and the really odd songs that get to live because of the extended time are often my favorites. Sign feels very complete to me, to the point there’s really only one song I’d leave off. In fact, there are too many great songs to talk about them all, so let’s focus on our case study of Great Prince Sides, and make an argument for Side One.

The opening track sets the tone for the entire album, as it does on so many Prince records. He’s addressing bigger topics this time, and doing so more skillfully than he did in, say, “Ronnie Talk to Russia.” While Prince lyrics can certainly be a mixed bag, there are lots of classic couplets here: “In France, a skinny man died of a big disease with a little name/By chance his girlfriend came across a needle and soon she did the same,” for one. Or, “A sister killed her baby ’cause she couldn’t afford to feed it/And yet we’re sending people to the moon.” The words also have a slightly playful vibe, though, which is why I think the song doesn’t sink under its own sobriety. “Let’s fall in love, get married, have a baby,” he suggests at the end, “We’ll call him Nate/If it’s a boy.” Well—okay by me.

Musically, we’re in midtempo one-man-band Prince land, which is a fine land to be in, though this time the music is powered not by Linn drums but by a Fairlight synth.² The song marches relentlessly for almost five minutes, the groove only falling away briefly after the lines “if a night falls and a bomb falls.” In the long outro we get some sharp lead guitar work, a synth drum break (and it works, I swear!). The song itself deconstructs in its final seconds, breaking back down to just that synth drum pattern, then instantly segues into what sounds like the noise of a city street.

“Play in the Sunshine” is a complete mood change. Higher-pitched keyboards, Prince singing about wanting to “meet you” and “kiss you” and then do “it all over again”: we are far away from AIDS and man ain’t being happy until he dies. “Before my life is done/some way, somehow, I’m gonna have fun,” a chorus of Princes sing, giving way to shouts of “Play!” while a guitar solo screams, and I’m all in. It’s an even better song than I remember it being, and I think the sequencing helps. It’s a huge shift in gears, and I think that helps the song feel even more manic.

“Sunshine” ends with ethereal, childlike voices, the music slowly breaking down; it feels like the end of one of those great summer days when you’re exhausted, and a little melancholic it’s over, but also still buzzed from all the fun. Then the song is abruptly cut off—it sounds as if a needle is being pulled across the record—and a new voice comes along and says, “Shut up, already! Damn.” Party Prince is here, singing in the voice of his female alter ego, Camille. Some of his dance party tracks don’t age well, but this is one I think sounds even better now—the music moves in more interesting ways than I remembered. “There’s a brand new groove going ’round,” Prince/Camille sings just as a cool keyboard suddenly comes into the mix, changing the mood—I love when words and music play off each other like that. There’s even a bridge of sorts (1:02, for example), and best of all, a consistently playful attitude. Some of his later dance tracks sound forced, like he’s working too hard, but how can you not love the man even more when he sings, “Let’s jam/Don’t wait for your neighbor/Green eggs and ham”? Horns, layers of vocals, a driving drum pattern, those funky Prince stabs on rhythm guitar: it’s all here. By the time he directly references the musical past he’s drawing on (“Let’s do the Twist/A little bit harder than they did in 66”) you understand just how well he’s pulled it off. The song ends with the same words it opened with—“Shut up, already! Damn”—but this time they are spoken in Prince’s natural voice, leading us into the side’s closing track, “The Ballad of Dorothy Parker.”

Where to start with “Dorothy”? For one, there’s a story that Prince didn’t even know who the real Parker was—he just liked the sound of the name.³ The narrator is a man who’s “kind of going someone” and has just been “talkin’ stuff/in a violent room.” He finds himself drawn to the attractive, intelligent, mysterious “waitress on the promenade.” Dorothy works the night shift, and is more confident and in control than many of the women in Prince lyrics: she’s the aggressor, asking our narrator if he wants to “take a bath.” She makes him laugh, gets bonus points for being a Joni Mitchell fan, and after his time with her our narrator “felt much better.” He goes back to the “violent room,” but this time takes a bubble bath with his pants on, the way he did with Dorothy, and “all the fighting stopped.” What does it all mean? It’s one of the Prince lyrics open to lots of different interpretations, which is one of the reasons it works so well.⁴ Do they actually have sex or not? Is Dorothy really a prostitute—is that what working night shifts “on the promenade” means? Is the violent room where he lives with this person he’s kind of seeing, or is it, like, the rest of the world?

The music is driven by Linn drums again, with a wonderful sort of futuristic jazzy feel. I think the direct reference to “Help Me” underscores this point, as do the wonky keyboards, which float in and out of time against that steady Linn groove. The layers of vocals are presented in a wide range of volumes and styles, and the whole thing just feels like it’s floating somewhere in space. It’s unlike any of the other three songs on this side, which are all also unlike each other.

And that perfect opening side lays out the template for the rest of the record. More dance tracks (The wonderfully dark-sounding “It” really holds up for me, “Hot Thing” sort of holds up, while “U Got the Look” is still the weakest song on the whole album); more odd, fantastic pop songs (“Starfish and Coffee” and “Strange Relationship,” the latter of which may just make my Top 10 Prince list, were I ever to try and construct it); appearances from Guitar Prince (most notably in “I Could Never Take the Place of Your Man”); and of course some ballads (“Slow Love” and “Adore,” which ends the album on a surprisingly sweet note). We even get a final track from the fired Revolution (“It’s Gonna Be a Beautiful Night”).

I could have gone into more detail on any of those songs quite easily, and the whole collection holds together beautifully. Like Parade, it’s even better than I remembered. The difference is, Sign is usually one of the two answer I give when asked my favorite Prince record. The other is just around the corner—but before that, we’ll need to take a little side trip. In the meantime, let’s watch him sing with Muppets.

1 The year after releasing Parade was a bit tumultuous, even by Prince-ian standards. He fired his band, whipped an album featuring a female alter ego name Camille, then handed Warner Bros. a triple album—and got annoyed when they thought such a move did not make sense for someone with declining album sales.

2 For my more technically-oriented friends, there are a lot of good interviews with Susan Rogers, his go-to engineer at this time. Like this one: https://www.officialcharts.com/chart-news/the-inside-story-on-the-recording-of-prince-s-legendary-sign-o-the-times-album__31053/

3 The story comes from Eric Leeds, who worked with Prince a lot, but I could also see Prince being the kind of guy who liked to fuck with people: https://www.songfacts.com/facts/prince/the-ballad-of-dorothy-parker

4 Not to spend too much time on the obvious, but also to make sure the point isn’t confused here: there’s a difference between lyrics that don’t mean anything and lyrics that are filled with lots of different potential meanings, yes?