Review: The Kaitlyn Fay Quartet at Jazz on Jay; Thursday, Aug. 13, 2026

Thursday at Jazz on Jay, Kaitlyn Fay said jazz-ified Broadway show tunes constitute her comfort zone, her bread and butter as a singer; and that songwriting is her scary frontier. She sounded confident in both, however, relying on her elegant, usually understated voice, going for flow more than fireworks, with expert swinging support by pianist Dave Gleason, bassist Dave Shoudy and drummer Bob Halek.

Kaitlyn Fay, above; below with her trio, from left Dave Gleason, keyboard, Dave Shoudy bass (acoustic and electric), Fay, and Bob Halek, drums

She started with the (over?) familiar “On The Street Where You Live,” definitely in her Broadway comfort-zone, but then added Latin syncopation to Gretchen Parlato’s more recent “Circling.” The tight trio swung both, and everything that followed – showing off her full palette early with the antique “Moonglow” then sailing past her scary (songwriting) frontier with the original “Library of Anxiety” whose uptempo Latin swing and agile skat-singing belied its horror-movie title. 

Gleason gloried in the solos that spiced every tune, Shoudy soloing more on electric six-string bass than upright and Halek pushing forward only late in the 90-minute show. In support or soloing, these guys are the trio any singer would love; and Fay surely did. And she earned a happy Halek grin when she nailed a complicated skat run in “Cockeyed Optimist,” title track of her 2025 album.

Dave Gleason, above; Dave Shoudy, below

Bob Halek

She stretched beyond the familiar flavor of “Street” and “Moonglow” – here, she swooped high – for Sondheim’s very Broadway “Everybody’s Got the Right” from “Assassins.” Then she brought up young daughter Quentin to duet in “Worthy,” also from “Cockeyed Optimist.” An able vocalist, Quentin showed precocious aplomb and the audience loved her.

Above: singers Quentin Fay and Kaitlyn Fay; below: with band

The show gained altitude and attitude, flying in “Blue Skies” as the band loosened into spirited riff-swapping and swinging hard in “This Could Be the Start of Something Big” – which had a big feel. They took “I Have Dreamed” from “The King and I” to Brazil as a punchy bossa with Gleason as terrific in this Latin mode as fans of his superb tropical band Sensemaya would expect. 

Fay paid sincere/playful tribute to WCDB/WAMC jazz DJ Bill McCann, by name, in the bluesy, bouncy “Radio Man.” And she kept the mood light with in a smooth shift from the comic to the sincere in “I Could Have Danced All Night.” Here, and throughout, she courteously danced backward from the mic to give the audience clear view of her trio. “Garbage Isn’t What It Used to Be” had a wry flavor; one of many Alan J. Lerner Broadway numbers she swung Thursday, this one is from the unfinished “My Man Godfrey.”

They turned serious, and sweet, with the stately “Old Time Revival Blues,” a Gleason/Fay original from “Cockeyed Optimist.” In its elegant nostalgic flavor, it evoked Allen Toussaint, and that’s a compliment. Fay’s vocal here stretched syllables over multiple notes, free and fine.

They closed hot with “Show Me” from “My Fair Lady,” exactly in Fay’s comfort zone, which actually seemed wider than she claimed.

Both keyboardist Gleason and drummer Halek are playing a double Thursday; at Jazz on Jay with Fay at noon and at Music Haven in the SUNY Schenectady’s Faculty Jazz Combo’s showcase with guest trumpeter Jon Faddis at 7 tonight.

Lanaea Bailey

Jazz on Jay Committee Chair and frequent host Lanaea Bailey announced her departure from both Jazz on Jay and her full-time programming position at Proctors Collaborative; she’s moving to Florida which needs all the sane humans it can get. Fittingly, she was the only listener to answer Fay’s quiz correctly: “What musical introduced the song ‘Everybody’s Got the Right’?”

Jazz on Jay continues Thursday, Aug. 20 with Alex Slomka and Friends; then concludes Aug. 27 with the Hot Club of Saratoga.