Much of his musical career has been devoted to the avant-garde and creative jazz world, however, and he has garnered considerable acclaim as a jazz sideman as well as leader of his own Todd Sickafoose Group. Like violinist Jenny Scheinman, Sickafoose is a West Coast native who moved east to New York City, becoming a key member of the Brooklyn jazz scene during the 2000s. While in California, the San Francisco native studied in Los Angeles with Charlie Haden and Mel Powell before returning to the Bay Area and joining the Scott Amendola Band and Scheinman's quartet; he can be heard on CDs such as Amendola's eponymous debut recorded in 1999 and Cry from 2003, as well as Scheinman's 2000 Live at Yoshi's. In 2000 Sickafoose released his first CD as leader of his own band, Dogs Outside on the Evander label. He also toured and recorded with genre-bending San Francisco singer/songwriter Noe Venable.

Sickafoose moved to Brooklyn in 2005, and when not touring with DiFranco could often be caught leading his own band or performing with groups such as Jenny Scheinman's Shalagaster at clubs like Barbès in Brooklyn or 55 Bar in Greenwich Village. In February 2006 the second Todd Sickafoose Group CD, Blood Orange, was released on the Brooklyn-based Secret Hatch record label. In addition to Sickafoose, the core quintet heard on the album includes tenor saxophonist Ben Wendel, trombonist Alan Ferber, guitarist Justin Morell, and drummer Ches Smith. Several guest musicians are also featured, including avant jazz guitarist Nels Cline, whose own largest audience during the 2000s came from his recruitment into the lineup of Wilco. Sickafoose's most ambitious recording yet as a leader arrived in June 2008: Tiny Resistors on Cryptogramophone featured a eight-piece group with Sickafoose on a variety of instruments (piano, Wurlitzer, vibraphone, marimba, and more) in addition to acoustic and electric basses. With sweeping, multi-layered compositions for the core octet supplemented by guest appearances from DiFranco and violinist Andrew Bird, the recording also displayed the bandleader's social and environmental consciousness on pieces such as "Pianos of the 9th Ward" and "Bye Bye Bees." While maintaining his alliance with DiFranco, Sickafoose continued leading his own ensemble into the 2010s while also serving as bandmember in a number of notable creative jazz groups led by others, including violinist Scheinman's Mischief & Mayhem quartet also featuring Cline and drummer Jim Black, and drummer Allison Miller's quartet featuring Scheinman and pianist Myra Melford. ~ Dave Lynch