Facing the challenges associated with leadership of a large creative jazz ensemble whose members had their own extensive performing and recording commitments (not to mention the daunting economics involved), Schuller turned toward a career leading smaller groups and collaborating with other artists as a valued sideman. He led the Schulldogs quartet during late '90s into the new millennium; the group featured tenor saxophonists Garzone and Tony Malaby along with the Schuller brothers George and Ed on drums and bass, respectfully, on the New World album Tenor Tantrums, released in 1999. Altoist Tim Berne replaced Garzone for the 2002 Playscape album Hellbent, recorded live in Albuquerque, New Mexico in 2000.
One of Schuller's longest-standing ensembles has been Circle Wide, formed by the drummer in 1999. The group's 2003 Playscape label debut, Round 'Bout Now, was a tribute to 1967-1970-era Miles Davis, and featured the drummer leading a core quintet that included trumpeter Ingrid Jensen, saxophonist/flutist Donny McCaslin, vibraphonist Tom Beckham, and bassist Dave Ambrosio (with guests Darriau, guitarist Pete McCann, and accordionist Sonny Barbato). McCaslin, Beckham, and Ambrosio returned for Circle Wide's 2008 sophomore outing, Like Before, Somewhat After, this time paying tribute to Keith Jarrett and featuring the addition of guitarist Brad Shepik to the lineup (along with Jamey Haddad guesting on percussion). In 2012 Playscape released Circle Wide's third album, Listen Both Ways, comprised mainly of Schuller compositions and featuring the quintet of Schuller, Beckham, Ambrosio, Shepik, and tenor saxophonist Peter Apfelbaum.