We Talked to Letters to Cleo About Being the Go-to Soundtrack Band of Your Favorite Teen Flicks

10 Things I Hate About You has earned its place in the official canon of the greatest teen films of all time—no point in arguing with us on this one. Released at the very end of the 90s, this modern take on The Taming of the Shrew was formative beyond encouraging a legion of girls that platform flip-flops, slip dresses, and strapless satin-y tops were de rigueur. (Actually slip dresses are back, so it seems the wardrobe stylist nailed something timeless with that one.) If you were anything like me, you probably envisioned your prom being as romantic as that moment when Heath Ledger’s Patrick Verona surprises Julia Stiles’s Kat Stratford with her favorite band, Letters to Cleo, and the pair receive a personal serenade of “Cruel to be Kind.” Watching it back now it also makes us miss Heath Ledger all the more— so fresh faced and green to it all.

It’s a given that a few notes, a little melody, a strident chord, can turn a movie moment on its head, but music is a particularly important facet of teen flicks—the bedrock, if you will—because it’s when you’re a teenager that music hits the hardest. When you’re 15 and going through it, every lyric applies, every artist has a particular and uncanny insight into your soul. Imagine any John Hughes film stripped of Oingo Boingo, Sigue Sigue Sputnik, The Psychedelic Furs or Orchestral Manouvres in the Dark? Do you think Judd Nelson’s fist pump during the closing scenes of The Breakfast Club would have been nearly as triumphant if Simple Minds wasn’t providing his theme tune? Do you reckon Phoebe Cates emerging from the pool in slo-mo in that fantasy scene in Fast Times at Ridgemont High would’ve been quite so epic, (or the cuts to Judge Reinhold jerking off been so amusing) without “Moving in Stereo” by The Cars? Nuh-uh.

Back in the 90s and early 00s, Letters to Cleo were all over the teen movie soundtracks of the era—The Craft, Josie and the Pussycats and 10 Things I Hate About You. (In 10 Things I Hate About You, the band even snagged that all important cameo). They provided the songs that made these teen drama resonate that much deeper. Formed in 1990 and led by Kay Hanley, the six-piece ermerged from Boston’s burgeoning alt-rock scene. The indie outfit most famously recorded a cover of Cheap Trick’s “I Want You to Want Me,” which would eventually find its way to the 10 Things I Hate About You soundtrack, but less-known is the fact that Hanley took on the vocals of Josie and the Pussycats for the 2001 movie (2016 marks its 15th anniversary). In front of the camera and behind the scenes, Letters to Cleo were the unsung heroes of 90s/00s cult teen films.

We caught up with Kay Hanley to find out how Letters to Cleo got involved with so many soundtracks over the years, what her kids think of her band, and the new music they have coming down the pipeline.

Noisey: Josie and the Pussycats Kay Hanly:

I remember when the soundtrack came out, and I wondered if Rachael Leigh Cook was singing in it because I was so young and didn’t realize another artist was backing her voice. As I grew up, I realized it was the same voice I heard on the 10 Things I Hate About You soundtrack.
It didn’t feel like we did more movies than other bands, but it sure turned out that way, didn’t it?

Tell me about all of the movies you were able to work on/in in the 90s and 00s.
Gosh. This producer we worked with was like the “soundtrack king,” but his specialty was having popular bands do cover songs. Basically he would corral all of his favorite bands, have them come to LA and record tons of cover songs. Then he’d pitch these bands’ songs to the movie studios and he’d end up getting a budget. You’d record it, stay at this awesome hotel and have so much fun. He was the one who ended up hiring us for The Craft and 10 Things I Hate About You. With 10 Things I Hate About You, we happened to be in LA and we happened to be recording covers for the movie and the director Gil Junger, needed a band to play “the band” in the movie. They were making the movie in Seattle. Larisa Oleynik was a huge music fan and apparently she was the one who found out we were doing music for the soundtrack and was like, “We have to get them.” It was fucking awesome. We had great times.

What was your favorite song to write for the soundtracks you worked on?
We didn’t write anything specifically for 10 Things I Hate About You. We recorded “I Want You to Want Me” by Cheap Trick. We were such Cheap Tricks fan, it was awesome. For Josie and the Pussycats, I co-wrote a couple of songs and Michael and I wrote “Shapeshifter.” That was my first experience as a gun for hire. I was just the singer on that—I didn’t have anything to do with it creatively. That was the first time I had done anything like that. Nobody had ever hired me just for my singing before.

After being such a big part of the soundtrack scene in the late 90s and early 00s, how do you think the cult-movie soundtracks have changed?
I don’t think they have. I think that music is an incredible way to sell a mood. It’s kind of how a director tells you how you’re supposed to feel in a moment. It creates completely different moods. The fact that you can even use popular songs to do that is kind of awesome. Directors who can use popular songs to create a mood without taking their heads out of the game entirely to do that… I think it takes a special kind of music to be able to do that. I think soundtracks haven’t changed—I think they serve the exact same purpose. For me, that was the band Family of The Year on the Boyhood soundtrack. I was like, “I have to figure out who that is.”

Do you have more than one kid now?
Yes, I have two.

Have your kids watched the movies you’ve soundtracked or been in? What do they think?There’s a picture I posted on Instagram a few years ago of Henry [my son] pausing a scene of 10 Things I Hate About You. He didn’t seem to acknowledge me, but I think secretly they’re super stoked that their parents were in these movies, and they have a band people care about. A lot of the reason why people care about our band is because of our work in films. I think we’re better known for 10 Things I Hate About You than our one hit we had.

According to your Wikipedia page, Letters to Cleo is working on a new EP and has plans to tour this fall. Is that true?
There’s a Letters to Cleo Wikipedia page?

Yeah! It’s extensive too.
Oh, cool! I’ve seen my Wikipedia page, but I don’t think I’ve ever seen the Letters to Cleo Wikipedia page. I should go check that out and make sure the details are correct. Yes, we’re making an EP. It’s our first recording in 18 years. We’re not going to do a full-on tour, but we’re going to do some dates in the fall. It’s totally for fun. We’ve all managed to stay in the music business, which is amazing, and we’re all quite busy with our careers, families and all that stuff. Doing something like this has to be a labor of love because we’re not going to make money off of it. I don’t think any of us is willing to quit our careers to pursue Letters to Cleo again because it’s not anything that’s interesting to any of us, but it is really fun. The stars aligned, and everything was very effortless and easy. We’re all tag-teaming the recording. It’s just fun! October or November we’ll be on the East Coast touring.

On that note, where has your career taken you over the past 18 years?
I’m a composer. My main job that I’ve been doing for the past couple of years has been writing the music for a Disney show called Doc McStuffins. I do a lot of music stuff for television. It keeps me very busy and very engaged and inspired. I write and record music every single day, and someone else sings it. [Letters to Cleo] is all doing that. Stacy [Jones], the drummer, is basically the music coordinator for bands. Michael produces a lot of indie bands and does a lot of mixing. He plays live with a lot of people. Greg [McKenna] still lives in Boston and has a studio out of his house. He’s a mechanical engineer. So, we’re all still doin’ it.

You guys reunited briefly in the 2000s. Did you plan to release an EP earlier, but it just didn’t happen?
No. We made a live record from that called Letters to Cleo: From Boston Massachusetts. It was just for fun. My god, that was almost eight years ago.

Ilana Kaplan hearts teen flicks and rad music. Follow her on Twitter.