Gress became interested in jazz and the double bass while a teenager, joining the Pennsbury Concert Jazz Band, a nationally-prominent high school jazz ensemble, in 1975, spending two years as bassist and arranger for the group. His interest in composing original material for large ensembles, such as those of Johnny Richards, Billy May, and Pat Williams, led him to Baltimore's Towson State University in 1977, where he studied composition and counterpoint with Hank Levy, known for his work with Don Ellis and Stan Kenton. While at Towson, Gress established a playing relationship with saxophonist Ellery Eskelin, with whom he cofounded Joint Venture with Paul Smoker and Phil Haynes. They released three albums on Enja Records between 1987 and 1994.
During 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 three live albums together and toured extensively.
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, Samo Salamon 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.
- Heyday (as Drew Gress's Jagged Sky) (Soul Note, 1998)
- Spin & Drift (Premonition, 2001)
- 7 Black Butterflies (Premonition, 2005)
- The Irrational Numbers (Premonition, 2008)
- And Again with Shims Trio (Deepdig, 2012)
- The Sky Inside (Pirouet, 2013)
With John Abercrombie
With Tim Berne
- Visitation Rites (Screwgun, 1997)
- Please Advise (Screwgun, 1999)
- Pre-Emptive Denial (Screwgun, 2005)
With Uri Caine
- Wagner e Venezia (Winter & Winter, 1997)
- The Goldberg Variations (Winter & Winter, 2000)
- Uri Caine Ensemble Plays Mozart (Winter & Winter, 2006)
With Joint Venture
- Joint Venture (Enja, 1987)
- Ways (Enja, 1989)
- Mirrors (Enja, 1994)
- Ralph Alessi, Baida (ECM, 2013)
- Ray Anderson, Big Band Record (Gramavision, 1994)
- Lynne Arriale, With Words Unspoken (DMP, 1996)
- Jon Ballantyne, The Loose (Justin Time, 1994)
- Don Byron, Romance with the Unseen (Blue Note, 1999)
- Marc Copland, Night Whispers (Pirouet, 2009)
- Marc Copland, Better by Far (InnerVoice, 2017)
- Dave Douglas, Five (Soul Note, 1996)
- Dave Douglas, Convergence (Soul Note, 1999)
- Yelena Eckemoff, In the Shadow of a Cloud (L&H, 2017)
- Yelena Eckemoff, Better Than Gold and Silver (L&H, 2018)
- Ellery Eskelin, Setting the Standard (Cadence, 1989)
- Erik Friedlander, Chimera (Avant, 1995
- Erik Friedlander, The Watchman (Tzadik, 1996)
- David Kane, Machinery of the Night (Magellan, 2006)
- Tony Malaby, Apparations (Songlines, 2003)
- Liam Noble, Romance Among the Fishes (Basho, 2005)
- Jason Robinson, Tiresian Symmetry (Cuneiform, 2012)
- John Surman, Brewster's Rooster (ECM, 2007)
- Tom Varner, Martian Heartache (Soul Note, 1996)