Inside the Making of the Super-Deluxe Reissue of Prince’s ‘Sign O’ the Times’

“I didn’t always give the record companies the best songs,” Prince told IndieLand in 2014, and no one knows that better now than former Warner Bros. A&R executive Michael Howe, who has served as full-time archivist for Prince’s estate since 2017. With a mammoth, no-holds-barred deluxe edition of Prince’s 1987 masterpiece Sign O’ The Times out now, Howe explains what it’s like essentially living inside Prince’s massive vault of unreleased material. Each reissue project starts with mounds of analog tape, which have to be digitized before Howe can start digging through the recordings. “It’s an enormous amount of material to bite into,” Howe says of the Sign O’ the Times box, which draws on what he calls a “wildly creative period of Prince’s artistry.”

There’s so much on this set. What was the universe of material you were drawing from?
The guiding principle with these sort of super-deluxe editions is that we try to put together the universe of possibilities for a specific creative era, and then whittle it back from there. This period of Prince’s life was extraordinarily prolific. It was basically a blizzard of creativity between about ’79 and ’92. Really until the end of his life, but certainly in the mid-to-late Eighties, he was just firing on all cylinders. So there was a tremendous amount of material.

We established general parameters, putting to the side anything that wasn’t specifically intended as part of the Sign O’ The Times creative process. Meaning no protégé work, and not really much of the instrumental stuff that ended up as part of the Flesh, or later, Madhouse. We had to be somewhat judicious, because it would have been completely unwieldy. So we basically looked at the [October 1986] dissolution of the Revolution, and the album they were intending to release called Dream Factory, for which there was a finished production master. And then what was the triple LP Crystal Ball, which then got whittled down to what became the double album Sign O’ the Times. We tried to put the bookends on either end of those two things.

We can now put together both Crystal Ball and Dream Factory as playlists, right, given this box and previous releases?
All of it is now available, thanks to the magic of streaming, to anybody who wants to assemble a playlist, which can be done. You can put together Dream Factory exactly as it was intended to be released. I think the final configuration was around July of ’86, so you can listen to it that way. And you can listen to the triple album of Crystal Ball.

There’s a striking alternate version of “The Ballad of Dorothy Parker” with a horn arrangement on there. How much time did you spend going through alternate takes?
I went through tremendous amounts of stuff. We sent hundreds of tracks for Bernie Grundman to master, and we kind of whittled it down from there. It was a tremendously forensic undertaking. We had to put about a third aside. So basically you have maybe two-thirds of what we initially envisioned might be part of the universe of possibilities.

What were the things that were most revelatory to you, as you went through?
I find myself going back to on a fairly regular basis to the 1979 version of “I Could Never Take the Place of Your Man,” which is something that we didn’t know existed until we kind of stumbled across it. Initially, we just found a rough mix on a cassette, which was undated. We thought perhaps it was a little bit later than it was. Then we finally found  the multi-tracks and the half-inch rough, which was dated April or May of ’79. It was kind of jaw-dropping to think that he had the song in his pocket for six or seven years before he reimagined it.

How did you even find it, given that it wouldn’t have been archived with this period?
It was dumb luck, frankly. It was early in the process.

There’s a version of “Power Fantastic” on the box where you can hear the band finding its way. What was the thought behind including it?
You hear Prince walking the band through the creative process. People think of him as a very exacting, perfectionist taskmaster in the studio, but you hear him literally saying something like, “There are no wrong notes, just let it happen.” Which is not a side of Prince people know about or get to hear about.

You got to listen to Prince’s work in the studio day-by-day. How did you hear his evolution in this period, particularly as he moved away from the Revolution?
The last super-deluxe deep dive that we did, which was 1999, was the end of his time as a solo artist, and was sort of the jumping-off point for when he became the band leader in the Revolution. This is leaving the band behind, and once again becoming the solo artist. So it’s very interesting to hear that dynamic. There’s cases on the box where you see it in two takes of the same song. In “Witness for the Prosecution” and “Big Tall Wall,” you hear a rock version, which was the Revolution version, and then the electronic-ish or funk-ish feeling of the solo version, which was a later take.

How did you select the live stuff that’s on there? And what’s with the absence of anything from the movie?
We had a number of different possibilities. We couldn’t really use anything that was contemplated for use in the Sign O’ the Times theatrical film, because there were all kinds of rights issues wrapped up in that which are basically too involved for me to disentangle on this call. We tried many, many different ways to include the theatrical release of the film, and couldn’t really do it in a way that we thought was complete and had the sort of integrity that Prince would have demanded for it. So we had to look at some other possibilities from a live standpoint, and the one that jumped out at us was the [June 20th, 1987] Utrecht [Netherlands] show, which was a particularly beloved show in the fan community and had never to my knowledge circulated as a finished stereo mix. I think there’s kind of a substandard audience recording that has floated around for a while. It was an incendiary show and shone a light on his live artistry at that point. And we chose the Paisley Park, New Year’s Eve [1987] DVD because it’s such an unbelievable performance, and also because, of course, it has the Miles Davis appearance.

There’s also a studio collaboration with Miles, “Can I Play With You,” which is a lot of fun. How much other material is out there from their studio work together?
There was more stuff that never really got finished as such.  There were other things that they were dabbling with, but nothing really ever came to fruition with it, which is unfortunate, to some degree, although the mystery of it or the promise of it might be more tantalizing than than the realities.

The general rule is that you’re not releasing unfinished work, correct?
Yes. Things that were put aside, that we think Prince did not return to in any kind of meaningful way — we left those alone, out of respect for Prince’s artistry and decision-making process.

So now that you’ve heard everything, was Warner Bros. correct to ask Prince to edit Sign O’ The Times down from the triple-album Crystal Ball version?
Well, I mean, that’s a very good question. My understanding, you know, I wasn’t there for the conversation, but [former Warner president] Lenny Waronker, with whom I worked for years, and who was very close to Prince, was the guy who had to call Prince and tell him that “We love the album, but we think it should be a double, not a triple” — which, unsurprisingly, I think, was not particularly well-received by Prince. But he complied. And in retrospect, I do think it was probably the the right decision. A triple album is is pretty difficult to digest, particularly in one sitting. I think it was probably the right thing to do. And certainly was a more concise view of what he intended to convey artistically. But, you know, I have a feeling Prince would disagree with me on that!

You now have a really vivid sense of just how much great music Prince was creating all at once in the Eighties. How do you make sense of it?
It’s kind of otherworldly. I’ve had the good fortune of having worked with a number of household names or iconic artists, and Prince was just orders of magnitude more creatively evolved than anybody I can think of. His guide vocal on stuff is better than most artists’ masters from take after take after take after take. The guy just had creative energy oozing out of him and was able to jump from genre to genre with complete authority, and without really losing any audience. From quiet-storm R&B to salacious, mechanoid funk to full-throttle arena rock to Mahavishnu Orchestra fusion. I mean, the guy was just un-fucking-believable, excuse my language. And every day, I have the good fortune of being able to recognize that firsthand.  It’s pretty remarkable, for somebody who loves music, to be able to immerse myself in this. If my 19-year-old self could see what I’m doing, my head would explode.

And I presume you’re continuing to work on future projects that perhaps cannot be named.
Yes, that’s exactly right. We’re very much on to the next couple of things under consideration, neither of which I can talk about, or none of which I can talk about. But it’s an ongoing process, for sure.