Wednesday, October 14th, 2026

Two Sets - 7:30pm | 9:30pm

Emmy-nominated Trumpeter and Vocalist Benny Benack III has

quickly become a leading voice in Jazz for his generation. He

headlines clubs and festivals around the world seemingly nonstop,

on the heels of his latest critically acclaimed live album “This Is The

Life” (2025) which has garnered thousands of streams and topped

the JazzWeek Radio Charts. He is the rare talent who is just as

formidable as a fiery trumpeter ranging from Freddie Hubbard to

Louis Armstrong and everyone in between, while as a singer he

delivers sly, mature, naturally expressive post-Sinatra vocal stylings.

His sophomore album “A Lot of Livin’ to Do” (2020) featured the

likes of bass luminary Christian McBride, achieving viral online

fame w/his vocalese rendition of "Social Call" ft. Veronica Swift

that's been transcribed and covered by singers around the world. He

has crooned his way to millions of more listeners alongside groups

such as the Grammy-winning “8-Bit Big Band” and YouTube

sensation “Postmodern Jukebox”. His (2023) album “Third Time’s

the Charm” went all the way to #2 on the charts and featured a

veritable line-up of special guests including Peter Bernstein, Bria

Skonberg, Chad LB & more.

His double-threat credentials were first apparent when he was a

finalist in the 2014 Thelonius Monk Competition on trumpet, and

then won Third Place in the 2021 Sarah Vaughan Vocal

Competition. His resume for both was recently bolstered by

Downbeat Magazine’s Readers Poll for 2025, where he placed #1 for

Rising Star Male Vocalist and was also #8 for Rising Star Trumpet.

His global recognition has been bolstered through his collaborations

with the GRAMMY-award winning “8-Bit Big Band” and touring

with Postmodern Jukebox. IMG Artists and Jazz @ Lincoln Center

have selected him to front numerous projects touring North

America, notably alongside fellow trumpeter Bria Skonberg and

young star vocalists Stella Cole and Kate Kortum. The recent

advent of live-streaming concerts has been a boon as well, both

through his residency at Smalls Jazz Club, as well as frequent

appearances at fellow superstar Emmet Cohen’s “Emmet’s Place”

online series. He has arrived as one of the most in-demand touring

artists and music educators in the Jazz world, with a never-ending

intercontinental schedule that reflects his indefatigable love for the

music, with his smile and panache on full-display wherever it takes

him next.

Winnie's Jazz's Upcoming Shows

The Winnies All Star Sextet featuring Sal Valentinetti