Music

“The worse singer I’ve ever heard.”

Gregg with Bruce Pedalty at the piano during a show in June 2025 (R. Novak Photography)

Gregg didn’t grab a microphone when he was five years old and wow a crowd with perfect pitch. He was 15 when he started singing in a high school musical, and even then it was only because all his friends were doing it. Yet when the music director called him the worse singer she had ever heard (true story), Gregg decided to begin classical voice training at the MacPhail Center for Music in Minneapolis.

He later developed his talent for jazz by studying with Twin Cities music educators Roberta Davis, Leon Thurman and Vicky Mountain.

With more than 30 years of experience, Gregg has performed as a jazz soloist, as a member of a vocal jazz quartet, and as singer and emcee with the Minnesota Jazz Orchestra, a 16-piece big band. 

He’s appeared at venues across the Upper Midwest, including the Dakota, The Times Bar & Café, Mystic Lake Casino, Artist’s Quarter, Bryant Lake Bowl, the Twin Cities Jazz Festival and the Wabasha Street Caves (Minneapolis-St. Paul), as well as Winter’s Jazz Club and Davenport’s in Chicago.

Gregg’s style is influenced by Mel Tormé, Sarah Vaughn, Mark Murphy and others. His classically-trained voice, “like butter” according to one fan (true story), brings smoothness, improvisation and energy into every jazz performance.


“I Didn’t Know What Time It Was” from the album Starting Point:


“How Does The Wine Taste” from the album Starting Point:


“Tangerine” with the Minnesota Jazz Orchestra
“One For My Baby” with the Minnesota Jazz Orchestra