Letters to Cleo’s Kay Hanley on the 20th anniversary of Cherry Marmalade and wanting to score Connor Roy’s wedding on Succession

In the 1990s, Kay Hanley found fame as the bandleader of Boston alt-rock outfit Letters to Cleo. The band’s 1993 single “Here & Now” helped them cultivate a national fanbase that led them to a series of placements in movies and TV throughout the decade. But it was an appearance in the movie — and on the soundtrack — for 10 Things I Hate About You that helped the band go mainstream. Just two years later, Hanley would become the voice of Josie McCoy in the now-cult-classic film Josie and the Pussycats, helping solidify songs like “Spin Around” and “3 Small Words” as pop culture phenomena. 

But during her tenure in Letters to Cleo, Hanley also released a solo record — Cherry Marmalade — back in 2002. The catchy pop album never quite hit the mainstream but found a following over the years. It also allowed Hanley to find peace and stray from the darkness shrouded in the sunny-tinged Cleo songs. For the album’s 20th anniversary, Hanley had an opportunity to revisit the record and release a new edition. “At that time, I never really liked the sound of my voice, so I’d never listened to the record until I went to remaster it for vinyl [for the anniversary edition],” she explains over the phone from Los Angeles.

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In an interview with AP, Hanley revisits the making of Cherry Marmalade, the Josie and the Pussycats vault songs that exist and what’s next for Cleo.

Tell me the origin story of Cherry Marmalade.

It’s from a book that I used to read to [my daughter] Zoe Mabel when she was a baby by this demented illustrator turned children’s book writer, Calef Brown. There’s a line from one of the poems in the book called “Introducing Ed,” and “Cherry Marmalade” is one of the lines from the poem in this book. It was always just so resonant to me. I hadn’t really planned on writing a solo record. Michael Eisenstein, my husband at the time, and now ex-husband, had just finished the tour for Letters to Cleo, and things had felt a little dark at the end of that last tour, for a variety of reasons. He was leaving for a couple of months, and I was partying my ass off, and I was like, “Oh, my God, my husband’s going to be gone. I’m just going to go crazy.” And literally 48 hours after he left, I found out I was pregnant. Everything just shifted. I quit doing all the drinking and the drugs, and I went to meet him in Maui four weeks later. He’d been surfing and taking really good care of himself, and I had been taking really good care of myself, and walking and eating, drinking juices and eating vegetables. We met as new people without ever expecting to.

What was the first song you wrote for the album?

At that point, I started writing “Galapagos,” which was a pretty dark song about the last Letters to Cleo tour, which felt like the end of Cleo for that period of time. I wrote “Galapagos” and a couple of other songs and brought them to Mike Denneen from Q Division Studios, who had made all the Cleo records. And he was like, “All right, we’re going to make a record.” I just kept writing, and we made a record together at Q Division. One of the things that were most remarkable about the experience of making that record was that I felt such a deep sense of peace and hopefulness that I had never really felt in my life before. I was pregnant with Zoe, and there was just this whole new sense of, “Whoa, the future.” I felt fearless in a way that I hadn’t, and I was able to write. Usually, the formula with Cleo is that I’d be really in a dark place, and I’d write all these very happy-sounding songs because that was how I coped — very happy-sounding songs with dark lyrics — and with Cherry Marmalade, I was able to really face a lot of that darkness and not be afraid of it.

[Kay Hanley with Letters to Cleo]

Did you care about how the record would be received at that time?

I didn’t really because I’d never made a solo record. And even in Cleo, I never had a sense of how to market myself. I made a record and put it out. By the time I went on tour, I was pregnant with [my son] Henry, so I was touring pregnant, again. By then, I was just like, “Fuck all, y’all. I don’t need you and your praise and your approval.” I didn’t need it the way I craved it when I was younger. So I didn’t even look. But people seem to like it now. It was one of the last records that Q Division to be recorded on the 2-inch tape that still was edited in Pro Tools. 

Looking back, do you have any regrets about how you approached the making of this record?

When I went into this process, I remember just thinking, “Oh, the vocals are too loud. It sounds this, it sounds like that.” But I had never really listened to the record. So when I listened this time around, I don’t think I would’ve done anything differently except for loving it more, then giving it more love and attention myself. I think maybe the thing I regret the most is how it was received by me, which is why it’s so wonderful to be able to come back all these years later and do it this way.

At this point in your life, which song from the record do you hold closest to your heart?

“Trans-Neptunian Object #1,” the closer, I love that. Especially because I wrote it about infant Zoe, and I’ve never really played that much live. It never made it into the live set, so I’m really looking forward to playing that one. “Galapagos,” always. I never get through that one without crying. I would say those are my two favorites today.

You were the voice of Josie from the Josie and the Pussycats soundtrack. Are there any unreleased songs from the movie that you’d ever bring out of the woodwork?

I mean, I have no control over it, but Dave Gibbs from the Gigolo Aunts, who brought me into the project, wrote a bunch of songs. There was a song called “Merry Go Around” that I recorded, and there were probably a couple of others from the early sessions. But they weren’t my songs, so they just didn’t make it to the record.

Oh, my God. We could get a Josie and the Pussycats EP?

Yeah, totally.

Incredible. The 10 Things I Hate About You soundtrack in general is so iconic, as is your part in that. How has that impacted your overall career?

Oh, my God. I don’t know. All I can tell you is that at the time, people liked the movie, and the same thing with Josie. I definitely felt the attention from those projects, but I did not feel love and adoration until the last five or 10 years. So, I’ve never perceived it as people being influenced by me as much as they’re influenced by what these projects had to say about girls and women. They were way, way ahead of their time. I’m not the least bit surprised that people finally came around and embrace these messages about girls and women and the space that we occupy in this world. So fucking proud to be a part of that.

Who do you dream of collaborating with at this point in your career?

Well, that would mean that I have to imagine getting back into life as an artist. Right now, my life as an artist is so part-time. I’ve been collaborating my whole life. My music life is very collaborative. That’s all I do, [so] there’s this incredible freedom in retreating into solitude to write, which I’ve never done in my life until now. So my favorite collaborator right now, the most challenging collaborator I have right now, is myself.

You’ve spent a lot of your career writing music for TV and film. Are there any shows you’re interested in making a soundtrack for?

Oh, my goodness. If I could write the theme song for Connor Roy’s presidential campaign in the next season of Succession, that would be amazing. I would love to do all those really goofy rap songs for Succession. Kendall’s always doing these dumb-ass raps. I would love to write the lyrics for those where he’s making up his own lyrics to Snoop Dogg songs.

Which artists were you most inspired by when you were making Cherry Marmalade?

I was just retreating into my record collection. I was listening to a lot of Big Star and the Muffs. Definitely Wilco. One of the songs was directly inspired by a film called Little Voice. I went to the theater and saw it by myself. I cried through the whole thing, just thinking about making the connection between going to this movie and this beautiful character finding herself and what was happening to me in my life. [So] I wrote a song called “Happy to Be Here.” 

What’s next for you?

Well, I created a show with my writing partners called Kindergarten: The Musical, which got greenlit, but we sold it to Disney Junior, got greenlit in the spring, so we’re in full-on production on that. I’ve never been an EP on a television show before, so this is a new thing for me. We have started writing a Cleo record, and I have started writing a new solo record. I’d love for that to be next year, so let’s just say next year.