However, Hemingway's membership in the Braxton quartet has not been the only high watermark in his career. While still drumming with Braxton during the early '90s, Hemingway began coming to prominence as a bandleader in his own right, heading a "transatlantic quintet" including American Mark Dresser from the Braxton quartet on bass as well as three musicians based in Amsterdam: cellist Ernst Reijseger, trombonist Wolter Wierbos, and saxophonist/clarinetist Michael Moore. Hemingway played drums and percussion and composed all of the quintet's original material, which can be heard on a number of acclaimed CDs. The ensemble's recordings include Special Detail (1991), Demon Chaser (1994), and The Marmalade King (1995), all on the Hat Art label and unfortunately now out of print. Two more recordings on the German Random Acoustics label are Slamadam (1995) and Perfect World (1996). In 1991, the band -- minus cellist Reijseger -- also made a quartet recording, which was released as Down to the Wire by Hat Art in 1993.

Hemingway disbanded the quintet after 12 years, citing the "formidable cost" of bringing the Netherlands musicians to North America for tours of the United States and Canada. Waltzes, Two-Steps & Other Matters of the Heart, the quintet's apparent final CD recorded at live European dates in 1996, was released by GM Recordings in 1999.

At the 1997 New York Jazz Festival, Hemingway premiered a new quartet with a shifting lineup drawing from a core group of musicians based in the United States. Quartet musicians included Ray Anderson or Robin Eubanks on trombone, Ellery Eskelin on tenor saxophone, and Mark Dresser or Michael Formanek on bass. While on tour in Europe during November of 1997, this new "American quartet " (with Robin Eubanks on trombone) recorded material for the CD Johnny's Corner Song, released by Auricle Records in 1998. Able to avoid the transportation costs associated with European musicians, Hemingway took the new band on the road for numerous appearances across the United States during 1998 and 1999. Key compositions performed on tour during this period were later recorded by the Hemingway quartet (with Anderson on trombone and Dresser on bass) for 2003's Devils Paradise.

Hemingway has also made forays into the world of contemporary classical music. He received commissions to write "Contigualis" for string quartet and "The Visiting Tank" for string quartet plus live electronics. These compositions were recorded in February 1999 at Merkin Hall in New York City along with two other works ("Aurora" for sextet and "Circus" for quintet), which were revisions of earlier commissions. The program was recorded for John Zorn's Tzadik label and released as the CD Chamber Works later in 1999. Hemingway has also received commissions for a concerto for percussionist and orchestra; a concert-length work for tape and percussion; a quadraphonic electronic composition; and a piece for multiple slide projectors, tape, and percussion, among other chamber and multimedia works.

Performances and recordings of solo percussion and electronic music have also been part of Hemingway's artistic endeavors. In 1996, Random Acoustics released Electro-Acoustic Solo Works (1984-1995) and Acoustic Solo Works (1983-1994), a pair of CDs documenting this facet of his career.

In addition to his own projects, Hemingway has been a member of ensembles led by bassist Reggie Workman and pianist Anthony Davis. He also participates in various collaborative groups, including BassDrumBone with Ray Anderson and bassist Mark Helias and a trio with Ernst Reijseger and German pianist Georg Graewe. In addition, Hemingway appears semi-regularly in a duo with pianist (and Braxton quartet alumnus) Marilyn Crispell; a trio with Crispell and bassist Barry Guy; Tambastics with Mark Dresser, flutist Robert Dick, and pianist Denman Maroney; and the Iliad Quartet with guitarist James Emery. Other musicians with whom he has recorded and performed include Derek Bailey, Leo Smith, Oliver Lake, Frank Gratkowski, Conrad Bauer, John Cale, and Hank Roberts.