Before Sarah Dooley made a name for herself in music, she was active in Chicago Street Theatre.
The 2007 graduate of Valparaiso High School performed in the melodic “Annie,” for instance.
Nowadays, Dooley lives in Brooklyn, N.Y., and dishes pop music, with a twist.
But succinctly describing it can be tricky.
“It’s always very difficult for me,” said Dooley, who performs her “More Stupid Things” show at 7 p.m. Sunday at the Chicago Street Theatre venue in Valparaiso.
“It’s piano driven, singer-songwriter type music,” she said of her distinctively adventuresome, and often whimsical, material.
“I always kind of compare it to Regina Spektor,” Dooley said.
Spektor is a singer-songwriter and pianist who forged a reputation in New York City with her captivating storytelling and alternative, but accessible, stylings.
Dooley likewise veers off the beaten path with clever, original ditties such as “My Body is Champagne,” which boats a wistful jazzy bent and tinkling keyboard work.
“Peonies,” meanwhile, carries a sweet, pensive edge, while “Watching ‘Goonies’ at My House” features Dooley’s signature work on the keys that bounces and delights.
Dooley’s solo show at Chicago Street Theatre is part of the venue’s One Night Jam concert series that kicked off in 2000 and has showcased Grammy-nominated country/American artist Gretchen Peters and Grammy-winning rock musician Jim Peterik, known for his work in the Ides of March and Survivor.
Dooley’s upcoming Sunday show is a sequel to last year’s appearance at Chicago Street.
“Her music is fun, quirky — and that fits her personality just fine,” said Valparaiso’s Paul Braun, director and production manager of “One Night Jam.”
Braun recalled when Chicago Street marketing director Eric Brant told him about a Dooley album a couple of years ago.
“I saw that it was sitting at No. 1 on the iTunes charts; I felt a sense of pride that one of our own was having success,” said Braun, alluding to Dooley’s “Stupid Things” album.
He noted that when Dooley played at the One Night Jam last year, the appearance ended up being “a huge success.”
This year, the 27-year-old singer is adding a different touch to her intimate, one-person show.
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“I recently got a mandolin,” the keyboardist said, relating that she is teaching herself how to play it, and writing songs for it. “I’m going to play three new original songs on the mandolin,” said Dooley, giving a hint of what’s in store for her Valparaiso audience.
Her musical influences include Fiona Apple.
“I love Carole King,” Dooley added. “I like Nellie McKay. She is brilliantly silly.”
McKay is a singer-songwriter and pianist who has often incorporated free-flow humor into her pieces that radiate jazzy, pop-laced elements.
Dooley’s experience with entertainment during her Valparaiso days not only includes performing in Chicago Street theatrical productions, but also taking on a classical instrument.
“I actually played violin all through middle school and high school,” she recounted.
“Ultimately, I would love to be just a working musician,” said Dooley, pointing to her desire to be on the road and make albums.
Bob Kostanczuk is a freelance writer.
Sarah Dooley
Where: Chicago Street Theatre, 154 W. Chicago St., Valparaiso
When: 7 p.m. Sunday
Tickets: $20; VIP $40
Information: 464-1636, ext. 1; www.chicagostreet.org