A fixture on the Chicago-area music scene since the 1990s, Vandermark has earned wide critical praise for his playing and his multilayered compositions, which typically balance intricate orchestration with passionate improvisation.

His father, Stu Vandermark, was the Boston correspondent for Cadence Magazine and currently is a noted essayist on jazz, primarily concerned with improvisation.

Although a trio, Lombard Street incorporated "suite forms" characteristic of later arrangements for groups of both substantial and limited instrumentation.

Developed further in Barrage Double Trio (e.g., "Agamemnon Sleeps") this simultaneously linear and episodic perspective on arrangement broadly has been the overarching architecture in most of his works for large-ensembles since that time.

Since then, he has performed or recorded with many musicians (including Hal Russell, Paal Nilssen-Love, Hamid Drake, Fred Anderson, David Stackenäs, Paul Lytton, Joe Morris, Ab Baars, The Ex, Mikolaj Trzaska, Marcin Oles, Waclaw Zimpel, Axel Doerner, Mats Gustafsson, Bartlomiej Oles, Wolter Wierbos, Joe McPhee, Zu, Peter Brötzmann, Fredrik Ljungkvist, Paul Lovens, Lasse Marhaug, Yakuza, Kevin Drumm, and members of Superchunk).

He was once a member of Witches and Devils and the Flying Luttenbachers and has led or co-led several groups, including DKV Trio, Free Fall, Territory Band, CINC, Sonore, the Vandermark 5, the Free Music Ensemble, School Days, the Sound in Action Trio, Steam and Powerhouse Sound.

Initial personnel were Vandermark, Mars Williams (saxophone), Jeb Bishop (trombone and electric guitar, though the latter was gradually phased out), Kessler (bass) and Tim Mulvenna (drums).

Their music could be broadly classified as post bop, though their earlier era had strong leanings towards punk rock and noise due to Bishop's ragged guitar contributions.

Active c. 2004–2007, the Free Fall Trio included Vandermark and two Norwegian musicians: pianist Håvard Wiik and bassist Ingebrigt Håker-Flaten.

Like Giuffre, Vandermark played clarinet and emphasized a rather hushed and subdued chamber jazz that still managed to swing and take creative leaps.

"[10] Personnel has varied but has always included Vandermark, Rempis and Fredrik Ljungkvist on reeds; Axel Dörner on trumpet and Per-Åke Holmlander on tuba; Jim Baker on piano; Kessler on bass and Lonberg-Holm on cello; and Paal Nilssen-Love and Paul Lytton on drums.

Territory Band also incorporates elements of noise and electroacoustic improvisation via the contributions of Kevin Drumm, who departed in about 2005 and was replaced by Lasse Marhaug.