Thinkin' Big at Black Squirrel

A 16-piece crew reminded modern audiences why big bands used to be so... big.

· 2 min read
Thinkin' Big at Black Squirrel

Taylor Kelly and Thinkin' Big
Black Squirrel Club
1049 Sarah St.
Philadelphia
Aug. 6, 2026

There’s a famous and often-cited Duke Ellington quote that speaks to the practical economic challenges of maintaining a big band. “There is nothing to keeping a band together.” Ellington quipped. “You simply have to have a gimmick, and the gimmick I use is to pay them money!”

It’d be hard to imagine in today’s landscape, but American popular music was once dominated by the sound of jazz big bands. Storied bandleaders like Ellington, Count Basie, Lionel Hampton and Benny Goodman once toured and packed dancehalls nationwide with well over a dozen instrumentalists in their employ. In addition to allowing jazz musicians to expand their collaborative networks, these large ensembles made for a fuller exploration of the music’s harmonic, rhythmic and melodic potential.

Today, the big band as a configuration is largely absent from jazz, with the exception of the bands that are maintained by universities and a few privately-funded institutions. Vocalist and trumpeter Taylor Kelly and bandleader and trumpeter Jonah Francese met in 2011 while playing in Francese’s 18-piece band Thinkin’ Big at Berklee. Since then, Taylor has moved to Philly and made waves in the local scene here and Francese is teaching in Chicago while recording and performing with Thinkin’ Big. Occasionally, the two old friends will reunite for a show that re-examines the big band’s infinite musical possibility.

On Thursday, Aug. 6, Taylor Kelly and Thinkin’ Big brought a 16-piece band to the Black Squirrel for an exhilarating night of classics and original compositions. Even during the tune up the sound of the band filled the room. It was visceral and all-encompassing as the full brass section, woodwinds, and rhythm section prepared to play. The first started with an original Francese tune with a grand opening melody that the band followed into a slow, steamy jazz-funk groove. The first tenor sax player stepped up with a fluent, swinging solo and the drummer’s nimble yet powerful solo was a highlight, proving that each member possessed considerable talents as soloists. In addition to the Thinkin’ Big instrumentalists, Kelly invited a handful of guest vocalists to add to the musical stew being cooked up on stage. Singer Gizelxanath Rodriguez joined for a gorgeous cover of “Dindi," a famous bossa tune composed by Antônio Carlos Jobim. Philly native Aquildawud and trumpeter and rapper Tennishu joined for a few fantastic originals and an impromptu freestyle session. It was an inspired evening of creative music. Taylor Kelly and Thinkin’ Big’s Black Squirrel show was as fun as it was ambitious. The big band brought out the full depth and breadth of both the timeless classics and contemporary gems.