When jazz singer Madeleine Peyroux brings her act to the Cistern Yard, it will be with a stripped-down trio of voice, bass, and guitar — a far cry from the full bands and string quartets she’s played with in the past.

Guitarist Jon Herington has been accompanying Peyroux’s fine singing voice, which has been compared to Billie Holiday’s and Edith Piaf’s, for about nine years. He was there for the full-band performances, but he says he has enjoyed interpreting Peyroux’s catalog of original songs and classic covers alongside bassist Barak Mori.

“Moving to a simpler format like this, one thing we realized right away was we all had to commit to trusting silence and space, that, OK, the only way we’re going to find any dynamic range with this kind of small, quiet three-piece thing is to really let it be as minimal as possible, one thing at a time,” Herington says. “If you can get used to that and get comfortable with that, with space and a sparser approach, then when everybody’s playing at the same time, it feels rich.”

Peyroux and Herington crossed paths after following divergent musical careers. Born in Athens, Ga., Peyroux got her start as a teenager busking on the street of Paris, eventually joining the Lost Wandering Blues and Jazz Band and touring Europe performing jazz standards.

Herington grew up in West Long Branch, N.J., musically reared on blues-rock and the sounds of the British Invasion. His high school band opened for Bruce Springsteen, then only a local hero, and he didn’t get into the jazz world until he attended music school at Rutgers University. Although he appreciated classical music, he quickly ruled out classical guitar as an option because he had already fallen in love with the electric guitar.

“If I was trying to be disciplined about playing the guitar, it seemed like the direction that made sense to me, because I had become more interested in jazz harmony, and it seemed like there was a lot more to learn there. It also seemed like there was a place for the guitar in that music,” Herington says.

He got rid of his solid-body Les Paul and picked up a big, fat Gibson Johnny Smith jazz guitar, starting on a musical career that would eventually take him to New York City. He says he took what work he could find: local gigs, teaching, weddings, bar mitzvahs, session recording. The big break finally came when he was filling in for a guitarist in the Broadway production of the Who’s Tommy. A fellow pit musician recommended him to Steely Dan as the legendary jazz-rock band was recording its 2000 album Two Against Nature, and he jumped at the opportunity. Herington has since toured and recorded with Steely Dan and other touring artists, and it was Steely Dan producer Walter Becker who ultimately introduced Herington to Peyroux.

“When I first started working with her, I was working as a musical director where I had a bit more control, but there was some friction, and I kind of resigned that role, preferring to just sort of play the guitar and let things work the way they worked naturally,” Herington says.

Trust, a key to any jazz act, grew with time.

“Over the years I think she’s learned to trust me a lot more than she did in the beginning, and I’ve gotten more comfortable and kind of figured out what she likes. It feels better than ever now,” he says.

Peyroux and her band have a knack for reinterpreting well-loved classics. Bob Dylan’s “You’re Gonna Make Me Lonesome When You Go” is transformed from a warbly folk-rock number to an intimate piece of shuffling jazz.

“On a lot of the moodier ones, the best strategy is to try to stick to simple, clear, beautiful-sounding parts,” Herington says. “It’s really quiet, too. She’s the quietest musician I’ve ever worked with. I mean, the band, you can talk over it. It’s pretty wild, and that’s kind of refreshing for me, actually, after like 13 pieces of Steely Dan onstage at the same time.”

The band also keeps quiet on Elliott Smith’s “Between the Bars,” which Herington says is his favorite cover to perform. The original recording was so sparse — just a guitar and Smith’s breathy voice — that even a simple three-piece band could trample the material without proper restraint. Peyroux’s version, which builds only slightly in intensity, will break your heart just as sure as Smith’s.

Ultimately, Herington says he had to encourage Peyroux to take a vocal solo on two or three songs in the Spoleto setlist. It’s a risky choice in the open air of the Cistern Yard as opposed to the intimate venues the band has traditionally played, but Herington says it’s worth the challenge. Maybe she’s harkening back to her busking days in Paris.

“She does sound best to me when she’s not pushing, very restrained,” Herington says. “But she has more lung power than you would know from listening to the records, I’ll tell you that. When she’s live, she will sort of go for it a little more.”

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