Jeremy Holiday remembers it well: at four years old, he got his first "pop" record, Daryl Hall & John Oates' 1980 blockbuster Voices. That record set him on an incredible path that readers of The Second Disc will no doubt recognize: the journey to a fruitful career in catalogue music. For nearly 25 years, Holiday maintained an incredible tenure in the major label reissue business, working at BMG's Buddha and Heritage imprints, surviving a 2005 merger with Sony Music (and BMG's divestment from the behemoth four years later) and working at Legacy Recordings overseeing everything from packaging to editorial and metadata and producing reissues and compilations for Rick Springfield, The Isley Brothers, Ray Parker Jr., Jermaine Jackson - and yes, the world's bestselling duo.

Since the late '90s, when he penned liner notes for the premiere CD release of Sacred Songs, Hall's prog-rock collaboration with Robert Fripp, most Hall & Oates CDs bear his fingerprints, from individual CD remasters to the career-spanning box set Do What You Want, Be What You Are (2009). "One of my real goals was to elevate their catalogue, but also the overall perception of them," Jeremy tells The Second Disc. "At that moment in time, they were quite underrated at the end of the '90s."

Indeed - thanks not only to that care but a myriad of factors including the group's live prevalence and the tenacity of manager Jonathan Wolfson - the duo went from ironic punchline to respected members of the pop/rock canon, making the Rock & Roll Hall of Fame in 2014. Tomorrow (April 1), as Hall embarks on a solo tour with longtime friend and collaborator Todd Rundgren, Legacy will release BeforeAfter, a double-disc offering of Hall's greatest solo works that Holiday co-produced and wrote the liner notes for. It's a perfect encapsulation of the magic that's entranced Holiday for four decades. "When it comes to Daryl as an artist, one of the things I love so much is that he means it," he says. "That performance is coming from the soul; there's nothing ironic or distanced or detached from it."

But that day also features another release on the calendar, representing Holiday's newest chapter in the music business. The release of an expanded edition of Graham Parker's Another Grey Area by the recently-revitalized Iconoclassic Records is Holiday's first as the label's vice president of business development and artist services. After years in the majors, Holiday's going back to his roots as a reissue storyteller on the third-party side, not only adding new CDs to Iconoclassic's sterling catalogue but bringing his many skills and talents from a lifetime of major label work into new realms. Iconoclassic's artist services wing has already helped create and optimize a YouTube channel for Australian alt-rock duo Syncretism (featuring vocalist Dave Scotland and guitarist Steve Koppes, the latter formerly of The Church) and helped get the bulk of rapper Doug E. Fresh's back catalogue delivered to digital music services.

On the eve of both BeforeAfter and Another Grey Area in record stores, Holiday was kind enough to chat with The Second Disc about his motivations and philosophy of music catalogue, why he'll never give up on CDs and the value of telling a good story with a reissue. This interview, conducted by phone, has been lightly edited and condensed.

First of all, it's great to see Iconoclassic back in the reissue game. Can you take us through the process of reintroducing the label to the world?

The story of Iconoclassic really goes all the way back to the 1998 BMG Special Products holiday party. That's when I, as a fresh intern at the just relaunched Buddha Records, met senior director of sales Frank Ursoleo. Despite the differences in our ages and levels of experiences at that point, a lifelong friendship immediately sparked over both of our mutual musical heroes, Daryl Hall and Todd Rundgren. That's a conversation that Frank and I have never stopped having.

In 2007, after Frank had moved on to Sanctuary Records and I had been with BMG Heritage and Legacy, we talked about starting a reissue label of our own. After a lot of soul searching, we determined the best course was Frank to run with the label and for me to continue my career with Legacy. Over the next decade or so, Frank established Iconoclassic as a fantastic reissue label that lived up to its mission statement of "Reissues Done Right." That means in terms of sound quality and mastering, packaging, liner notes, the overall presentation.

One of the nice things for me was in my role at Legacy, I was involved with third-party labels. My team was responsible for delivering label copy, credits, art assets to the third-party labels before it went into production. So even though I wasn't part I still got to have involvement through my work on the Sony side and see some of the great work Frank and the team were doing.

Flash forward to 2021. My career at Sony drew to a close, and one of the first calls I made was to Frank as a longtime friend, just to share the news of what was going on in my life and career. Pretty instantaneously, he offered the opportunity to rejoin Iconoclassic and carry it forward.

The first new project under the revived Iconoclassic is Graham Parker's Another Grey Area - what made you want to take on that album?

This is an artist that really perfectly fits into what Iconoclassic is about, but there's definitely a personal aspect as well in this choice. When I went to college, on the very first day at Rutgers, my parents gave me a little bit of money. While the majority of kids were meeting each other and checking each other out, I walked down to a record store I had seen and used that money to purchase Passion is No Ordinary Word: The Graham Parker Anthology. From that moment, Graham's music and his point of view were really the soundtrack to my college years. Another Grey Area was one of the first Graham records I connected with. It's a great record, perhaps a bit misunderstood at the time. It's his first record without The Rumour, and it sounds a bit different than records that came before - but I think it's important to understand that was his intention. He was trying to do something a bit different. It's a record he's always been proud of - and I wanted to reintroduce it for the 40th anniversary.

While I was at Legacy we started to do digital backfill. In 2013, I compiled this track list and it was released digitally. The initial plan was to take what was done and release that physically. But listening to it, I heard what we had done was a Mastered for iTunes release. That was absolutely perfect for the time, but it wasn't necessarily the right master for CD release. So we went back with Mark Wilder and did a completely new mastering. It's the best this record has sounded on CD.

What is the most gratifying part of the third-party licensing approach? What is the most challenging?

The most gratifying is to see the amount of love for the work the label has done. There are people who have written to us that they have the complete Iconoclassic catalogue. The label hasn't released anything new over the last couple years, but it hasn't been forgotten about. The reaction from fans has been incredible.

And getting to work on true passion projects. The records we're releasing are not picked simply because we think that they may do well. We believe in the music, we believe in the artists, and we believe there's a need for these projects to exist. Some of the pieces along the way - as a liner note comes in, just reading it and knowing all the right people have been interviewed, that a story is being told for the first time - is incredible.

As far as what's most challenging: I think it's important to understand that a third party label is different than being a repertoire owner. Iconoclassic will enter into agreements with repertoire owners for different catalogue. I would compare it to owning a house and renting an apartment. Renting, you're entering into an agreement for a limited term with limited rights. Through no fault of their own, I think the audience doesn't understand that, and look for us to do certain projects that simply would not be possible - not because we wouldn't want to do them, but because the circumstances would not allow for this project to happen.

Iconoclassic is not only doing reissues now - it's also making moves into "artist services." Can you touch a little on what that means and what you offer for clients?

The role I came into Iconoclassic to do is a business development role. There have been various different aspects to that. In terms of the label side of things. It's largely been about forging and renewing relationships, A&R - but also putting in place different structures that will enable the label to do a variety of deals that will enable it to work with a larger variety of repertoire owners.

The other piece is our artist services subdivision. Myself and the various people who work on Iconoclassic releases are all music business survivors. Over the last number of years, while physical will always be our first love, we've developed a variety of skill sets that are not necessarily devoted to physical. It's a means of creating solutions for clients - artists, management, labels, etc. - on a freelance or retainer basis.

How do you deal with the challenges of marketing titles that the artists are not necessarily available to "participate" in? What, to your mind, is the best way to reach fans of older music who might not be as "plugged in"?

One aspect I'm putting a lot of attention into is our social media presence. The label has always had one, and I'm working hard to make it be more consistent. To build an audience so that when we are releasing something, we have a larger audience of our own we are speaking to.

It's interesting - in my work in reissues over the years, I've found a lot of projects that don't have participation have been some of the most commercially successful over the years. That depends on the artist and how iconic their status may be, but I don't necessarily think it's a barrier to doing a release.

I'm thinking ahead to an unannounced project - it's a solo artist that's deceased. In terms of the liner notes, we wanted to tell the story of this record. But the person who created it isn't here to tell that story, and there's not a lot of existing material of the artist telling the story of this record. But through reaching out to all the different people who were part of it - about 10 musicians, songwriters, producers, engineers - we were able to create an amazing oral history in the liner notes that ran 6,000 words. Then hopefully, once this record comes out, all of those people can be ambassadors for the album.

That's one of my favorite aspects of the B.T. Express release. The members that played on that record haven't been an intact band since the '70s. And they haven't been interviewed that much over the years. A. Scott Galloway, our liner notes writer, is one of my favorite people to work with - he tracked down everybody, and they have wonderful stories to tell. The stories are absolutely there and are interesting, and I'm thrilled the Iconoclassic release is presenting the story of this release for the first time. It makes that reissue so much more than if it was only putting the music back into the marketplace. That storytelling aspect does set this release apart.

Do It ('Til You're Satisfied) indicates that you'll be pursuing all genres with Iconoclassic, beyond the genres and artists the label is known for working in. Can you talk about the "branching out" process?

One of the interesting things is sometimes the perception versus the reality. When I look over the history of the label, its first couple releases were Laura Nyro. Its next couple were by The Isley Brothers. There have been a lot of different things strewn through its history. But I do think the perception of the label is it's late '60s/early '70s rock label. That's based on some of the really really great work it's done with The Guess Who, Canned Heat, Grand Funk Railroad and Jefferson Airplane.

Going forward, this label loves early '70s rock, and will absolutely be continuing to release other projects in line with what people's expectations might be. But I think there's a real opportunity to go down different roads. I see B.T. Express as being of a piece with the Isleys, perhaps Earth, Wind & Fire. I know also there are more things that will further the context of it. We're working on an Ohio Players project which will be announced soon. It'll tie together a little more.

We're doing a 2CD deluxe edition of The Light User Syndrome by The Fall. That probably seems the most far afield from the things the label has done in the past. But then you look back and see the label has done things with the '80s Lou Reed records; this is sort of a further step down that road.

There's so much wonderful music out there. I think of Iconoclassic as an approach to catalog, not a strict genre label. What does stay consistent is the time period it's covering: that will remain music from the '60s through the '90s. But in terms of genre, there's so many wonderful records there. And I do tend to think that people's tastes are not as narrow - that people like a lot of different music.

Your first two releases are CDs. Do you anticipate trying your hand at vinyl? Do you have a personal preference?

We do envision doing some vinyl titles in the future. It's not the focus right now - it's pretty well known that there's a lot of production delays at the moment. As a player that's not been in the vinyl field before, it does not necessarily make sense at this moment to pursue too many vinyl titles. I think once things open up a little more, and it's possible to do things with a better return time, that's something we'll look into.

For what it is we do, I think the CD is the ideal medium. Storytelling and context are such an important piece of what we do. Some of those concepts I think the CD is really the ideal medium for that kind of musical storytelling. If vinyl offers a wonderful tactile experience and streaming offers endless choice and convenience, I think the CD offers this canvas of musical storytelling. The catalog business you and I love so much - so much a piece of that is storytelling.

I'm a huge lover of the CD format. It almost makes it seem like we knew what we were doing, that at the same time we're releasing CD titles again, there's pieces written about a CD revival. The numbers are growing significantly, year on year, for the first time in awhile. I hope anyone who either has not experienced CD or anyone who has moved away in the last couple years will rediscover it. It's a wonderful way to experience music - and it's different. Not better or worse!

You've written the liner notes for BeforeAfter, a Daryl Hall solo collection, hitting shops the same day as Another Grey Area. Was this planned or just good luck?

It's either dumb luck or divine intervention! It's Daryl's baby - something he's so proud of and so behind. I offered my point of view, but ultimately, the choice of repertoire and the sequence is his. He came up with a record that flows, and tells a story he wants to tell. It's a story that really - having studied him as a fan for over 40 years but also having worked with him over 20 years - this record feels more like Daryl Hall than any of the other projects I've had the pleasure of working on with him.

It was an unbelievable experience working with him on this. Daryl Hall is absolutely the reason and inspiration for why I'm here, why we're having this conversation. Just like Graham Parker was the soundtrack for my college years, Daryl is the soundtrack to my life, virtually from the beginning. His music means as much to me now as it ever did. And when it comes to the liner notes, I think that's why he asked me to do them, because he knows that I get what he's about as an artist. Not everybody that's ever written about him really gets what he's about. For any artist, that can be frustrating.

How does it feel to be "back" working with Hall after decades of work on the Hall & Oates catalogue?

I try to be a music business survivor. Along the way, you evolve with the industry, and the work you're doing evolves. For the last couple years, I had not been working on physical product or even reissues. Having the opportunity to work on BeforeAfter and the Iconoclassic reissues really reconnects to that pure love for catalogue, for musical storytelling, for compiling, for remastering, for CDs - all of that stuff.

The reason I wanted to do it in the first place is that pure love for it. All of this stuff, I may have lost sight of it a little bit. It wasn't as though I was unhappy doing the work I was doing over the last couple years. But coming back to this work was like coming home. It feels right. It feels like the perfect fit.

What do you get from Daryl's solo material, and what do you hope fans who are maybe less familiar with it get out of this set?

What I hope people get out of it is how eclectic he is, how comfortable and natural he is working in different styles people may not necessarily associate with him. He'll go further into a particular direction [as a soloist]; there may be elements of prog on the '70s records, but Sacred Songs he went fully in that direction. Soul Alone - there's no "rock and soul." That's a straight soul record.

One of the unique elements of his solo career is you can hear him going all in on certain styles, then the next record is going to go in a different place. There's so much he's interested in, musically; there's so much he's great at musically, and there's so many people that want to collaborate with him.

You see that with Live from Daryl's House as well - and one of the cool aspects about the record is that there's eight tracks from LFDH episodes. That music has not really been released on record. It shows him going in and out of different styles, working with different people - some of whom he might not be expected to work with. You see how natural those collaborations are, and the respect that's there, mutually.

What areas of opportunity do you want to see catalogue music explore?

Music is the actual opportunity. There's a lot of talk about content, certainly. A lot of talk about NFTs, and platforms - I think there's not as much talk as there should be about music, artistry, creativity. There's almost an opportunity in the fundamentals that are perhaps being overlooked at the moment.

What music enriches your spirit right now?

I've been on a big Roy Ayers kick lately. So much great music he's been involved with through the years. Music that's been speaking to me quite a bit - it has a great feel, a great vibe. You can't feel stressed or negative listening to him.

Your work in the music business has found you going down many paths. What keeps you going?

That there's still work to be done. There's so many artists I love where there's a project that hasn't happened yet that I believe should happen. I know what that project is in my own mind, and I want to make it a reality.

It's amazing: after all this time, there's no shortage of ideas. And not only my own! I love when people come to me with their ideas. The people who I really respect - whether someone like Donald Cleveland, or yourself, or Joe, or, Frank, or John Sellards or Edward ODowd or Ralph Chapman - when any of these wonderful people bring something up, maybe I haven't heard that record. But I'll pretty quickly come to understand it the way they do, because we're speaking the same language.

And if I were to stop doing this, I would miss the conversations. I would miss the music. I wouldn't want to be somebody standing on the sidelines, critiquing what other labels are doing. I want to be in the arena. It's not easy - it's a tough industry. It always has been, it always will be.

But it's really rewarding and enjoyable to do great projects, and see the reactions from people paying money for these projects and enjoying them. And not to put too fine a point on it, but people are hurting right now. Everybody's dollar is going less far than it even did a month or two ago. If they're spending money to buy a record, which is really a luxury, I want it to be as great as it possibly could be. And when people reach out and say they love the work that was done, it's so meaningful.

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