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With a kindergarten-inspired musical in the works and two shows at the Paradise, Kay Hanley’s past is very present

Kay Hanley and Letters to CleoChris Sikich

For Kay Hanley’s latest project in her second career as a Hollywood songwriter, she’ll revisit being 5 years old. “Kindergarten: The Musical,” currently in production for a 2024 launch on Disney Junior, will be an animated series that begins on the first day of, yes, kindergarten.

“Everything you’re ever going to learn in your life — all the miserable stuff, all the happy stuff, all the friend stuff, all the paranoid stuff — all of it happens to you when you get to that classroom for the first time,” Hanley says. “The smallest things are huge. We get to write stories about these tiny slices of life for a 5- or 6-year-old that turn into these huge musical productions.”


Scouring her younger years for creative inspiration has become a successful career for Hanley, who will serve for the first time as executive producer on “Kindergarten: The Musical.” She created the show with her writing partner, Michelle Lewis, and Charlton Pettus, a writer and touring member of Tears for Fears who is originally from Brookline.

Hanley will take another walk down Memory Lane, to her mid-20s, when her band, Letters to Cleo, plays a pair of shows at the Paradise this weekend.

The band — which broke up around 2000, reunited briefly in 2008, and has been back together again since 2016 — is celebrating the 30th anniversary of its debut album, “Aurora Gory Alice.” Surfing the alternative rock tsunami of the mid-1990s, the record rode the barrel after it was re-released on a major label.

“There’s a couple of songs I’m not, like, ‘Woo-hoo!’ to play,” Hanley admits with a laugh. “But most of ‘em I’m psyched to play. It’s a really cool time capsule for all of us, thinking about songs we wrote when we were basically my kids’ age.”


The band stayed busy through the ‘90s, culminating in an appearance as themselves in the romantic comedy “10 Things I Hate About You” (1999). Next they recorded a dozen songs for a cartoon. By then, however, they were ready to break up, and Hanley had found her second act. She provided the singing voice for the lead character in “Josie and the Pussycats” (2001), which opened the door to two decades of steady work in Hollywood.

“I didn’t want to be in a band when Cleo broke up,” she says. “I really wanted to go behind the scenes. I didn’t know that I wanted to write for cartoons, but I knew that I didn’t want to be the front person of a band. I didn’t want to show myself.”

After a while, she also didn’t want to be in a relationship, which she was, with LTC bandmate Michael Eisenstein, the father of her two children, Zoe Mabel and Henry Aaron. The end of their marriage was rough, Hanley says, but they have grown to be friends again.

“It’s such a failure when a marriage breaks down. It’s so hurtful to everyone involved, especially the kids. But Michael and I, we’re each other’s people.” Both are now remarried.

“We have a very warm and professional relationship,” Hanley says. “We will have dinner, all four parents and the kids. That’s, like, my favorite dinner date.”

She and Eisenstein have also begun to write songs together again. With co-founder Greg McKenna, drummer Stacy Jones, and bassist Joe Klompus, Letters to Cleo just released two new songs — “It’s Sunny Outside,” a love/hate letter to LA, and “Bad Man,” an abuse victim’s revenge fantasy.


“Like a lot of songs I write, they’re parables, sort of allegories,” she explains. “I have been in abusive relationships. I have not been married in one, but it has happened. But those people don’t even deserve songs about them.

“Michael and I just started writing, and for some reason I was thinking of steeping someone’s tea with nightshade.” That ominous line led to the darkly comic story behind the song.

For this weekend’s shows, the band invited its old friends the Gigolo Aunts to open. That band’s Dave Gibbs moved to LA in the late ‘90s. He helped Hanley land the “Josie” gig and has had his own successful career in Southern California, where he now co-owns a top-rated wine bar.

Letters to Cleo in concert at the Paradise in 2017.Josh Reynolds for The Boston Globe

“We played together all the time back in the olden days,” Hanley says.

Now clean and sober, Hanley is frank about her struggles with alcohol. She tells a wild story about the night the band celebrated the release of “Aurora Gory Alice” at the late, lamented T.T. the Bear’s Place, which was its “home away from home.”

After the show, Hanley confronted a police officer who was hassling the band headlining The Middle East next door for leaving its van in a no-parking zone.

“With my tiny white-girl privilege, I’m going to reason with the police,” she recalls. But the officer “did not take kindly to this at all, and he starts yelling at me. And my Dorchester came out.”


When her bandmates tried to restrain her, she struggled to break free, and “inadvertently” hit the officer. The next thing she knew, she was face-down on the hood of the police cruiser, being handcuffed.

Thankfully, she says, “there was no internet back then. Can you imagine? So many of the things I did were not documented for posterity, and I’m really happy about that.”

What was documented were the band’s bright, super-melodic songs, which have carried on. In its heyday, Letters to Cleo shared stages with Weezer, Oasis, the Breeders, and dozens more bands whose music has not held up quite as well.

“My third act is taking me into some very interesting places,” Hanley says. “I’m having a great time.”

So why make the effort to organize more shows with the group that dates back to her young adulthood?

“Because I don’t need to!” she says emphatically. “If I needed to, I would hate every second of it.”


With Gigolo Aunts. At the Paradise Rock Club, 967 Commonwealth Ave. Nov. 17-18 at 7 p.m. $35.

James Sullivan can be reached at Follow him @sullivanjames.