To celebrate the 30th anniversary of Prince's Sign 'O' the Times, we asked eight of our most purple-loving writers to answer five big questions about his double-album masterpiece. Is it his best work? Which of its 16 diverse, sophisticated songs are the best, and on the flipside, which is the least significant? Would we have been better off getting the originally planned three-disc Crystal Ball set instead, and could the album have been an even bigger hit if he had released different songs as singles? Here are their answers..

Is ‘Sign o' the Times’ Prince’s best album? If not, what is and why?

Michael Gallucci: Sign 'O' the Times is Prince's masterpiece. Purple Rain has some better and more popular tracks, but that album sounds more like a collection of great songs. Sign 'O' the Times is a great album masterwork, with a beginning, a middle and an end. It all flows together. And that double-record length helps fortify its standing.

Nick DeRiso: Not only do I think it’s his best album, I think it’s one of the few – one of the very, very few – examples of a double album that actually warrants the expanded length. There are times, if you are incredibly fortunate, when everything comes together for an artist – and this was one of those times. Only three of the 16 songs here have a co-writer, and all of them – save for “It’s Going to Be a Beautiful Night” – basically feature Prince performing all by himself. Yet it doesn’t play like a one-man-band record, nor does it sound as insular as his upstart early solo albums. Rendered by a supremely confident figure at the tail end of a huge decade, Sign 'O' the Times instead covers the full breadth and depth of his genius like no other Prince album.

Bill Wilson: Yes, along with Purple Rain & 1999. Every track is a great Prince song, with at least five that belong in his all-time Top 20: the title track, "The Ballad of Dorothy Parker," "If I Was Your Girlfriend," "Adore" and "I Could Never Take the Place of Your Man."

Mike Joseph: Sign 'O' the Times is, indeed, Prince's best album. Not only is it his best album, I'd argue that barring Stevie Wonder's Innervisions, it's the best album made by ANYONE ever. Mastery of multiple genres, multiple sounds, multiple instruments, multiple voices. It's what happens when you're at peak creativity AND you have a chip on your shoulder. Dirty Mind, Purple Rain and 1999 are all five-star albums (and Controversy is, like, a 4.85). But Sign 'O' the Time reigns supreme over them all.

Michael Parr: As a singular recorded statement, there is no better representation of all Prince (and the remnants of the Revolution) had to offer at what is arguably his creative peak than Sign 'O' the Times. Likely due to the fact that Sign was the culmination of his working on several projects at the same time. It was essentially "the greatest hits you hadn't heard yet."

Jed Gottlieb: Absolutely not. Yes, the double-disc set is a masterpiece in its own sloppy, funky, wild way, but Purple Rain clobbers it (and Dirty Mind might top it too). What’s so great about Sign 'O' the Times is that it takes dramatic risks. I can’t think of a predominantly pop artist who would release a slinky, stiff robotic groove like “It” or stuff a long jazz break into a song as hooky as “I Could Never Take the Place of Your Man.” So cool and at the same time those risks can make for a bumpy ride. That said, side three is probably the pinnacle of Prince.

Dave Lifton: I don't know if it is, but it's certainly the one where he took everything he had been trying over the previous four or five years and ramped up the ambition. That said, it's pretty much my go-to Prince record when I'm in the mood for him, because the diversity of ideas and sprawl almost makes it seem like its own greatest hits album.

Matthew Wilkening: This is a debate that's so difficult, there have been situations in my "real" life where I've said, "This is like choosing between Sign o' the Times and Purple Rain." Here's how I've finally come around to thinking about it, as a hardcore Prince fan - Purple Rain belongs to the world, but Sign 'O' the Times is ours. If you meet someone new who professes to be a big Prince fan, and they don't start talking about this album in particular very quickly, you pretty much know they're full of it. Plus, Prince has never sounded more connected to the real world, in terms of both lyrics and sonics. The 1999 drum machines and synthesizers are completely gone; it sounds like he wandered into the same studio where Stevie Wonder recorded his masterpieces.

What is the best / most important song on 'Sign o' the Times,' and why?

Gallucci: The title track sounded like headlines being scanned for their urgency at the time: AIDS, drugs, the Space Shuttle explosion ... And the spare, robotic beat that drives the entire thing gives it an impassive tone that's both harrowing and eye opening.

DeRiso: Might be an obvious choice, but I’d say the title track. With its street-level imagery and minimalist beats, “Sign 'O’ the Times” rightly could have been viewed back then as Prince’s nervy attempt to come to terms with the commercial emergence of hip-hop – but it's aged remarkably well. Certainly, his message remains as timely as ever.

Wilson: "I Could Never Take the Place of Your Man." For many casual fans I often heard them refer to this song (and the video) as the moment they realized Prince was a guitar God.

Joseph: I don't know if I can choose a "most important song". "Adore" was influenced by the quiet storm sounds of Luther Vandross and Anita Baker (and a healthy dose of Al Green) and trumps those artists' entire catalogs. The title track was a catalog of societal ills that was quite unexpected coming from a superstar act that was thought to live in an ivory tower, and "If I Was Your Girlfriend" was a gender-f---ed tale of friendship and relationship dynamics that was 30 years ahead of its time. Trying to decide what's the most important or impactful of those songs gives me a headache.

Parr: On a record this diverse, it's hard to pick a singular "best," but "If I Was Your Girlfriend" endures. In the guise of 'Camille', Prince was free of the trappings of sexual identity and delivered one of his most complex lyrics.

Gottlieb: “U Got the Look” is a dark horse for greatest Prince song. Well, it’s not that dark, more like a deep purple. But the title track takes it. Popular opinion pegged Prince as a hedonist (and he often gave people reason to believe that), but he penned deeply political music. At a time when too many of his (would-be) peers were singing gooey love songs aimed at teens and the Top 40, Prince dropped an anthem that exposed urban ills such as AIDS, gang murders, poverty, and the proliferation of devastating drugs. He gets sexy and dirty and fun later on, but “Sign 'O' the Times” opens the album letting us know there's more to life than heavy breathing.

Lifton: "I Could Never Take the Place of Your Man" is my all-time favorite Prince song. It just explodes out of the speakers from the opening. I love the lyrics so much; he's looking to get some but then he backs away when he realizes that she needs more than that. It's kind of noble, especially coming from a guy who wrote so many songs about getting loose and freaky. You've also got three amazing guitar tones -- that distorted crunchy rhythm, the fat lead in the solo and those slinky stabs in the verse. And that moment when the keyboard harmonizes with the guitar for a few seconds? God, that's just perfect.

Wilkening: If it weren't for the title track, this would be a very interesting race between maybe a half-dozen songs - "I Could Never Take the Place of Your Man," "Starfish and Coffee," "Housequake," "If I Was Your Girlfriend," "The Ballad of Dorothy Parker" and "Forever in My Life." But there's a reason "Sign 'O' the Times" was the lead-off track and first single for this ambitious project: It draws a sharp line in the sand, separating itself from the baroque sound and romantic imagery of Parade. This sets the perfect tone for the new levels of musical and lyrical sophistication and experimentation of the following 15 tracks.

What is the “worst” / least great or least important song on the album, and why?

Gallucci: "Slow Love" is the forgettable middle song on the album's weakest side. But at least the other four tracks hint at the album's more ambitious origins and, at the very least, serve as pieces to the Crystal Ball puzzle. "Slow Love" is one of Prince's by-the-numbers slow jams, something he'd dive into more and more over the years. A sign o' the boring times to come ...

DeRiso: Though it’s got a great new-wavey groove, I never really bought Sheena Easton as the saucy duet partner in “U Got the Look.” She’ll always been the “Morning Train” lady to me, I suppose.

Wilson: "It."

Joseph: "It" is the most throwaway song on the album. I skipped it for a long time, but I'm finally beginning to come around. It's just weird to hear such a frivolous song when the rest of the album feels so creative and weighty.

Parr: Though it ties Sign to the famed Crystal Ball, "Hot Thing" seems inessential. The same could be said of "It," which ups and flips the "Darling Nikki" paradigm on its head and submits to his singular obsession.

Gottlieb: Probably “Play in the Sunshine.” The hippie feel makes it seem like a leftover from Around the World in a Day. On an album filled with endless experimentation, huge hits, and introspective soul, the track feels flat.

Lifton: "Hot Thing" bores me. That groove worked better on the title track and "It's Gonna Be a Beautiful Night" was a better James Brown vamp.

Wilkening: If you pointed a gun-shaped microphone at me, I guess the answer would be "Slow Love," but how can you really say anything bad about a song with such beautiful horns? The real reason it doesn't seem as special now is that he tread on this territory so many more times in the future - "Damn U," "Insatiable," "Scandalous," etc.

Would the three-disc ‘Crystal Ball’ have been a better album?

Gallucci: I don't think so. Sign 'O' the Times feels like a bit too much at times; expanding the set to three CDs would only encourage the bloating. I'm glad many of those songs exist in some form, but few albums are worth two LPs, let alone three. I've never listened to Sign 'O' the Times and thought, "I wish this could go on for another 45 minutes."

DeRiso: I think expanding this to the 22 tracks generally credited to the shelved ‘Crystal Ball’ set would have necessarily diluted its considerable power. That said, I’d have rejoiced at the inclusion of “Rockhard in a Funky Place” or “Shockadelica” in place of “U Got the Look” – which, having been recorded late in December 1986, was the only new addition to the reworked track listing that became ‘Sign o’ the Times.’

Wilson: Yes, 100 percent. "Joy in Repetition" (another Top 20 Prince song of all time) alone makes it a better album. Then add "Rebirth of the Flesh," "Rockhard in a Funky Place," and "Shockadelica," and Sign 'O' the Times becomes even more of a masterpiece, if possible. It was a big mistake by Warner Bros. not to release it as the original three-album collection. Plus, the entire face-painting "Slave" era could have been avoided.

Joseph: While the songs that didn't make Sign 'O' the Times are all good (and "Joy in Repetition" is somewhere in the canon of best Prince songs of all time), I think the tight two-disc edit is what makes the album as good as it is. Most of the songs that got cut are kinda fluffy by comparison.

Parr: If Matt Fink is to be believed, there never was an album called Crystal Ball, rather it was a tune that was dropped due to the band's (at this point, the expanded version of the Revolution) inability to make it work live. That said there is little doubt that Prince had designs on creating a narrative—would it have been a better record is debatable. The additional tracks most commonly included have all seen release in one form, or another, making it as easy as putting a playlist together to roll your own. Now if we were talking about Dream Factory

Gottlieb: Name your favorite triple album. Take your time, I’ll wait. If you’re a bluegrass nut I’ll give you the Nitty Gritty Dirt Band’s Will the Circle be Unbroken? But let’s be real, even George Harrison’s All Things Must Pass could use a little pruning. For Sign, I’d cut “Play in the Sunshine” and live cut “It’s Gonna Be A Beautiful Night” and make it tighter and not expand it as Crystal Ball would have done. Prince has very few duds, but also never knew when stop and let an album be.

Lifton: Triple albums are way too much music. Even for Prince.

Wilkening: No. But good golly, I still want to hear it. And I also want somebody to explain exactly why he used that same title for 1998's oddly (and too often, poorly) chosen triple-disc collection of unreleased tracks.

Did Prince hurt the album’s chances for larger commercial success by releasing "If I Was Your Girlfriend” as the second single - and if so, was it worth it anyway?

Gallucci: The title track, even though it hit the Top Five, was pretty weird. "If I Was Your Girlfriend" is a great song, and I like it as a single, but it was an odd fit on mainstream radio at the time. Still, Prince's previous album, Parade, yielded only one Top 20 single; Sign 'O' the Times had three Top 10s, so the single's low showing on the singles chart was just a small snag. His commercial powerhouse days were waning by then anyway. Prince was always one of pop's riskiest artists. ‘If I Was Your Girlfriend” was one of several that didn't quite pan out in the end.

DeRiso: As much as I love this song, it certainly hurt him commercially. Musically rather bleak, vocally odd and lyrically stupefying for the times, it was a gust of patented Prince weirdness when most listeners were probably hoping for something lightweight and fun after the darkly topical title track. That said, would he even be Prince without that kind of sex-bending audacity? Moves like this may not have sold him more albums, but it certainly cemented his legend.

Wilson: Yes and yes. It's one of his best songs ever but not a commercial single choice to make coming off of "Sign 'O' the Times" – but in many ways I'm glad he did release it as a single, as it did get more exposure for a classic Prince song.

Joseph: I don't know what the hell Prince was thinking by releasing "If I Was Your Girlfriend" as the second single. It shouldn't have been a single PERIOD. There was no way radio was playing it (rock radio, pop radio OR black radio--which was mighty conservative at the time). A guy who was already seen as a weirdo singing about being his girlfriend's girlfriend (and, let's face it...Prince being Prince, we're not sure if he meant "girlfriend" or GIRLFRIEND, if you know what I mean...) using a pitched-up female-sounding voice? No commercial prospects at all. Would Sign 'O' the Times have been a bigger hit had he gone with "U Got the Look" or, say, "Hot Thing" as the second single? I dunno. Probably. But he didn't, and it's fruitless to suggest what might have been.

Parr: The pop world wasn't ready for Camille, but it reconnected him with urban radio at a time when his art was increasingly alienating—in other words, worth it.

Gottlieb: Yes, it did. The song is so damn intimate. It destroys gender roles, plays with the lines between love and lust and friendship, shows Prince at his most vulnerable. All this over a backing track that’s slow, cold, and dark. If the album’s singles had been, in this order, “U Got the Look,” a radio edit of “I Could Never Take the Place of Your Man,” “Starfish and Coffee,” “Slow Love,” this would Prince’s second best-selling album (after Purple Rain, naturally).

Lifton: The next two singles went Top 10, so it couldn't have sunk it too badly. Still, there was no way "If I Was Your Girlfriend" could have been a hit. I can imagine the feud between he and Warner Bros. over releasing it, and the label had no choice but to give in. It wouldn't be the last time they fought.

Wilkening: Of course it did. And some part of him probably knew it would, or at least that he was taking a commercial risk. But that's exactly the spirit - "Let's take the bass out of 'When Doves Cry'" - that made him so unique. If "U Got the Look" came out second and a shortened "I Could Never Take the Place of Your Man" next, he might have sold twice as many albums. But then again, if that happened Sign 'O' the Times wouldn't be such a perfect "real Prince fan" litmus test.

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