Durnig the 1980s in the Baltimore/Washington DC area, he played with Sonny Stitt, Clifford Jordan, Albert Dailey, Mose Allison, Zoot Sims, Cab Calloway, Buddy Hackett, Phyllis Diller, and pianist Marc Copland, with whom he still plays today. He also served on the faculties of the Peabody Conservatory, Towson State University, and the Baltimore School for the Arts. He formed a quartet, Tekke, in 1989 with David Kane, Glenn Cashman, and Michael Smith.
In 1997, he cofounded the cooperative improvising trio Paraphrase with saxophonist/composer Tim Berne and drummer Tom Rainey. Together, they pursued a compositional approach to free improvisational practice. They recorded two live albums together and toured extensively until 2002.
In 1998, he released his first album as leader, Heyday, with his band Jagged Sky (featuring David Binney, Ben Monder, and Kenny Wollesen). 2001 saw the release of Spin & Drift with Uri Caine, Berne, and Rainey, in which he played pedal steel guitar for the first time.
Since 1992, Gress has maintained an extensive touring schedule, traveling to Europe, Asia, and South America. Those with whom he has and continues to work include Tim Berne, Ravi Coltrane, Uri Caine, John Hollenbeck, Fred Hersch, Marc Copland, Don Byron, Steve Coleman, Dave Douglas, Jack DeJohnette, John Surman, Ray Anderson, Erik Friedlander, Kenny Werner, Bill Carrothers, Ralph Alessi, Tony Malaby, Steve Lehman, and Edsel Gomez. To date, he has appeared on over 140 recordings, 4 of which have received Grammy nominations.
Gress’ own ensembles have toured Europe four times since 2002, in addition to isolated festival appearances in Italy and Portugal. In 2004, the UK’s BBC Radio and London’s Guardian selected his quartet’s live radio broadcast as Jazz Concert of the Year.
Composition awards include an NEA grant (1990), funding from Meet the Composer (2003), a Chamber Music America New Works Grant (2005), a CMA French-American Exchange Grant (2007), and an Encore Grant from that same organization (2008). He continues to compose for larger groups and has begun experimenting with virtual synthesizers.