The Fat Cat Big Band is an eleven-piece New York band that plays nothing but the music of its guitarist, Jade Synstelien, and it took its name from the basement pool hall and jazz room at 75 Christopher Street where it spent its first decade. The band exists because of one booking. Synstelien, born August 17, 1974 in Minneapolis, moved to New York from Taos, New Mexico in June 2001 wanting to build an orchestra big enough to play what he was writing. Mitch Borden, who had run Smalls on West 10th Street and had opened Fat Cat as an offshoot, gave him a room to rehearse and a standing Tuesday night. The band's first gigs, in September 2001, were billed as the Staring into the Sun Orchestra, which is still the name of Synstelien's publishing and production company. In 2006 he renamed it after the club, and the Tuesday slot eventually became a Sunday one.

Eleven players is small for a big band and the instrumentation is deliberately lean: two trumpets, a trombone and a bass trombone, three saxophones, and a rhythm section of guitar, piano, bass and drums, with Synstelien leading from the guitar chair rather than from a podium. The band's own press kit makes the point directly, that the Fat Cat Big Band does with eleven musicians what other big bands need close to two dozen to do. The chairs have been filled from the pool of players working the Smalls and Fat Cat rooms, which by the late 2000s included musicians who also held seats in the Mingus Big Band, the Vanguard Jazz Orchestra, the Roy Hargrove big band and the Jazz at Lincoln Center Orchestra.

Everything the band released on record comes from two days. On July 15 and 16, 2008, at Clinton Recording Studios in New York, the eleven-piece cut thirty-one original Synstelien charts, and those thirty-one tracks became three albums for Luke Kaven's Smalls Records, the label attached to the same pair of clubs. Meditations on the War for Whose Great God Is the Most High: You Are God (SRCD-0042, eleven tracks) and Angels Praying for Freedom (SRCD-0043, ten tracks) were issued together on March 15, 2009. Face (SRCD-0047, ten tracks) followed on October 15, 2009, completing what the band called its debut trilogy. Bryan Smith engineered and mixed all three, Nathan James mastered them at The Vault Mastering Studios, and Synstelien co-produced with Samantha Merley, who also did the photography and design. Every sleeve carries the line "Blessed by Billy Kaye," a nod to the drummer who worked with Thelonious Monk and Stanley Turrentine and was by then one of the managers at Fat Cat. The personnel is identical on all three records. A separate six-track promotional sampler, Tasting Menu, drew selections from the three and was issued without a label the same year.

The trilogy got a good press for a self-contained house band on a tiny label. Mike Shanley in JazzTimes credited Synstelien with "adding to the legacy of big band music rather than emulating its past glories." Michael Steinman wrote in Cadence that the leader was "bringing highly developed arranging craft to music of marked accessibility." Mark Corroto and Duck Baker both covered the records for All About Jazz, Baker calling the band one of the most refreshing groups to come along in years, and Edward Blanco's review of Face in January 2010 called it the best of the three. David R. Adler named the band in the large-ensemble category of his top 25 of 2009. Allegro Media handled distribution in the United States, with Late Set Records taking the albums in Japan.

The club that named the band did not survive. Fat Cat closed at the start of the COVID-19 pandemic and the space reopened as Cellar Dog on June 30, 2021 under different ownership. The band moved up the street. It had already been playing Smalls, where the SmallsLIVE archive documents its dates back to April 3, 2010 and forward through December 6, 2022, including a July 23, 2017 program of Mozart's Requiem swung for the eleven-piece and a November 11, 2018 set on J.S. Bach, Billy Strayhorn, Duke Ellington and Basie alongside Synstelien's own charts. The roster turned over steadily across those years while a core held: Synstelien, Phil Stewart on drums, Jack Glottman on piano, Max Seigel on bass trombone and Alexi David on bass appear again and again.

After seventeen years without a new record, a fourth album arrived. We Must All Be Free!, thirteen tracks and the band's first release not drawn from the 2008 sessions, came out on August 17, 2026 on Staring into the Sun Production Co., Synstelien's own imprint. Its titles carry the same argumentative streak as the trilogy: "Prayer for Gaza / No War," "The Mississippi River and This Land That I Love," "The Waltz of Goosebumps for Eric Dolphy and Johnny Hodges," "Federal Reserve System Blues (Part 1)." No personnel has been published for it and no review of it had appeared as of this writing.

Synstelien writes for the band as a composer first and an arranger second: the group has never recorded a standard, and its live programs of Bach, Mozart, Strayhorn, Ellington and Basie are his own arrangements rather than repertory charts. What he does with eleven players is treat the two trumpets, two trombones and three saxophones as a real section when he wants weight and as seven soloists when he does not, which is why the records sound bigger than the payroll. The writing sits in a bebop and post-bop harmonic language with the swing kept intact, and the titles do a lot of the talking: prayers for freedom, compassion, togetherness and New Orleans on one record, a piece named for the room's owner ("Blues for Borden") and one for two of its own players ("Road Song for Stacy Dillard & Alexi David") on another. Synstelien names Charles Mingus, Bach, Jimi Hendrix and Native American chant as his sources, and the band has drawn comparisons in print to the orchestras of Ellington, the Count Basie Orchestra, Mingus, Quincy Jones and Lionel Hampton. Away from the band he is a classical guitar transcriber, with three published collections of Bach fugues, canons and two-part inventions arranged for solo guitar.