The Chicago-based avant-jazz unit Vandermark 5 are led by reedist Ken Vandermark, who founded the group in 1996 with saxophonist Mars Williams, trombonist Jeb Bishop, bassist Kent Kessler, and drummer Tim Mulvenna. The group's recording debut came early the following year with Single Piece Flow on the Chicago-based Atavistic label. The quintet returned in 1998 with Target or Flag, and each successive release garnered the group increasing critical praise. Saxophonist Dave Rempis replaced Williams prior to the Vandermark 5's third LP, Simpatico (1999). The group became a favorite at jazz festivals, and in 2000 released its fourth album in four years (all on Atavistic), Burn the Incline. The following year brought their newest installment, Acoustic Machine. The band then changed drummers, welcoming Tim Daisy as the new man behind the kit. His first album with the band was 2003's Airports for Light.

The Vandermark 5 continued performing and recording prolifically throughout the 2000s, issuing the further Atavistic releases Elements of Style...Exercises in Surprise in 2004, Color of Memory in 2005, Discontinuous Line in 2006, and Beat Reader in 2008; Discontinuous Line marked the first recorded appearance of cellist Fred Lonberg-Holm (who joined the group following trombonist Jeb Bishop's departure in 2005) as a member of the quintet. Four of the band's Atavistic CDs included bonus discs entitled Free Jazz Classics, and featured interpretations of music by the likes of Ornette Coleman, Cecil Taylor, Anthony Braxton, Julius Hemphill, Sonny Rollins, and Rahsaan Roland Kirk. The discs were subsequently released as Free Jazz Classics, Vols. 1-2 and Vols. 3-4. Alchemia, a massive 12-CD set documenting the Vandermark 5's residency (with Bishop included in the lineup) at the club of the same name in Krakow, Poland during March of 2005, was issued later that year by the Polish Not Two label. Not Two also released another live set by the group in 2010, The Horse Jumps/The Ship Is Gone, recorded live during June 2009 at the Green Mill in Chicago, with the quintet supplemented by Swedish trumpeter Magnus Broo and Norwegian pianist Håvard Wiik, both members of Scandinavian free jazzers Atomic. ~ Jason Ankeny & Dave Lynch, Rovi