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Go solo with Letters to Cleo’s Kay Hanley in Boston

The Dorchester native will mark the 20th anniversary of her solo debut, "Cherry Marmalade," at City Winery.

Kay Hanley performs at the 2019 Hot Stove Cool Music benefit at Paradise Rock Club. Matthew J. Lee/Globe Staff

As the parent of a daughter whose elementary school years coincided with the rise of “Hannah Montana” on The Disney Channel, I spent an inordinate amount of time hearing the music of one Ms. Miley Cyrus, who played that show’s titular character. And I remember thinking, “Sounds like Hannah Montana has been listening to Letters to Cleo.”

Of course later I realized why Miley and some of her 2000s teen-pop brethren might have been taking cues from (sorry, The Lemonheads, it’s true) Boston’s most engaging ’90s alt-rock band: Turns out that after Letters to Cleo’s run of three stellar albums in the 1990s, Dorchester’s own Kay Hanley — the lead singer and mastermind behind the group — shifted toward kids’ entertainment. 

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During the first decade of this century, Hanley provided backing vocals for Cyrus on stage, songs for shows like “Generation O!” and videogames like “Sonic the Hedgehog,” and — most iconically, some would argue — the singing voice of Josie in 2001’s “Josie and the Pussycats” movie. So it’s not a stretch to see how she might have influenced the young music-makers of the period — and they could have certainly done a lot worse in terms of musical mentors. 

After all, Letters to Cleo’s output, notably their breakout 1993 record “Aurora Gory Alice” and its wild and wooly follow-up, “Wholesale Meats and Fish,” in 1995, was some of the best alt-rock of a decade chock full of it, combining elements of guitar grunge, new-wave melodies, and, thanks to Hanley’s expressive vocals and winking attitude, a sense of fun not always present among their generally downbeat contemporaries. It’s an attitude that carried over into Hanley’s also-excellent solo work, like 2002’s more pop-oriented but still spunky “Cherry Marmalade.”

And it’s that album that will take center stage when Hanley brings its 20th anniversary tour to City Winery for two shows on Sept. 30 and Oct. 1, in front of what’s sure to be a lively local crowd of friends, longtime Letters to Cleo followers, and probably more than a few latecomers. 

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“We realized that many people have become fans after the band broke up,” Hanley told Chaos Control last year, prior to last November’s two Letters to Cleo shows at the Paradise. “A lot of people had been fans for almost 20 years and had never seen us. It was super cool to have all these people we never thought we’d see. To connect with a whole new audience was really gratifying.”

And now she’ll have a chance to do it on her own, on her home turf — not something Boston fans of alt-rock, the ’90s in general, or “Josie and the Pussycats” would want to miss.

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