Purple Rain may be Prince’s biggest-selling and arguably best album, but 1999 was his most pivotal. After releasing four scandalously excellent records of erotic R&B, he put some pants on, toned down the Lothario act, and rebranded himself as a pop savant, and the record’s synthy crossover bids like “Delirious” and “1999” coupled with the steamy vulnerability of “Little Red Corvette” set him up for superstardom. But perhaps the most surprising aspect of 1999’s success was that it was a double album without too much bloat (though the lyrics to “Lady Cab Driver” have not aged well). It was a lot of music, but it was also just enough, and that fact is all the more impressive considering Prince was busier than ever, writing for the Time and Vanity 6 in addition to making the album. Somehow he kept the quality up.
This has never been more apparent than on the six-disc, Super Deluxe Edition 1999 box set, which pairs the album with two discs of mostly unreleased outtakes from the fabled vault and electrifying live recordings from the era. It’s like an alternate universe for the album.
On an early version of the Batman-era B-side “Feel U Up,” he plays a scuzzy, squeaky keyboard line, as if it were an extension of 1999’s synth masterpiece “D.M.S.R.” There are also stunning live-in-the-studio takes of 1999’s “International Lover” and the B-side “How Come U Don’t Call Me Anymore?” that show how the album might have sounded looser if that’s what suited his whimsy. “Vagina” is a regrettably titled guitar rocker about a hermaphrodite (the refrain goes, “Half boy, half girl, best of both worlds”) that could have worked perfectly on Controversy or Dirty Mind. “Can’t Stop This Feeling I Got” is a Farfisa-organ–accented rocker that radiates the same positivity as Controversy’s “Private Joy.” He plays a jaw-dropping guitar solo throughout most of the funky “Rearrange,” flexes the Minneapolis Sound in a way that might inspire Bruno Mars and Mark Ronson to rip him off again on “Bold Generation,” and even dabbles with a reggae skank on “If It’ll Make U Happy.”
The collection also contains artifacts that Prince obsessives have long read about but never heard, like an early studio version of “Possessed,” which marries his loose, funky Seventies sound with the keyboard overload that became his fixation in the early Eighties. And even though casual Prince fans probably won’t care to hear four more minutes of 1999’s already perfect “Delirious,” there’s now a full-length version of it with even more drum machine honky-tonk turnarounds (something he experimented with more on another outtake, “No Call U”). And then there’s the “music-as-a-drug” song “Purple Music,” which, along with the purple sky in “1999,” is notable as one of the first times Prince sang about his favorite color.
None of the bonus songs are necessarily better than the ones that made the cut on 1999, but they show just how curious he was at the time, trying out new and different ideas, musical themes he would still be exploring in the decades that followed. You can also hear how “professional” he and his band were at the time, as they flit between airtight funk on songs like “Head” and loose jamminess on “Little Red Corvette” on the live recordings. There are a few well-known outtakes that could have been added to the bonus disc — most notably, the collection’s producers omitted “Extralovable,” a track he originally wrote for Vanity and rewrote it for himself in 2016, because the original referenced sexual assault — but then again, how many discs would be in the collection if everything was included?
As with the Purple Rain box set a couple years ago, this macro look at 1999 shows not just Prince’s genius but the breadth of his brilliance at the time. The songs that made the cut on 1999 — which already lasts more than 70 minutes — were just a sliver of what he was doing at the time. What’s left is for you to ponder all the musical thoughts and ideas he didn’t record.