Reginald Workman was born June 26, 1937, in Philadelphia, Pennsylvania. He played piano, tuba, and euphonium as a boy before settling on double bass in the mid-1950s. He came up working with Gigi Gryce, pianist Red Garland, and drummer Roy Haynes in the late 1950s, and also recorded during this period with Donald Byrd, Duke Jordan, and trumpeter Booker Little.

In 1961 Workman joined the John Coltrane Quartet, replacing bassist Steve Davis. He is heard on Coltrane's Olé Coltrane (Atlantic, alongside a second bassist, Art Davis) and on the core sessions of Africa/Brass (Impulse!), and he toured Europe with the group that November, documented on "Live" at the Village Vanguard. He also appeared with Coltrane and Eric Dolphy on a West German television broadcast that survives on video. Workman left the group after the European tour and was succeeded by Jimmy Garrison.

From 1962 to 1964 Workman held the bass chair in Art Blakey's Jazz Messengers, in a lineup with Freddie Hubbard, Wayne Shorter, Cedar Walton, and Curtis Fuller, recording Caravan, Ugetsu, and Free For All. He then worked in Yusef Lateef's group (1964-65) and became one of the most in-demand bassists on Blue Note's roster through the decade, recording Shorter's own Night Dreamer and Juju (both with pianist McCoy Tyner and drummer Elvin Jones), Lee Morgan's Search for the New Land, and dates for Grant Green. He was equally active on the era's freer wing, appearing on Archie Shepp's Four for Trane (1965, with John Tchicai, Roswell Rudd, and Alan Shorter reworking Coltrane compositions) and, later in the decade, on Pharoah Sanders's Karma (1969), where he and a second bassist (Richard Davis, then Ron Carter) anchored the two side-long pieces including "The Creator Has a Master Plan." He also worked in this period with Herbie Mann and Thelonious Monk.

Workman began leading his own record dates in the 1970s, starting with the Japanese-only Conversation, credited to "Reggie Workman First" (Denon, 1979) and The Works of Workman (Denon, 1979), a bass feature coordinated by Tsutomu Ueno. In 1978 he co-founded the Super Jazz Trio with pianist Tommy Flanagan and drummer Joe Chambers, and he formed the Reggie Workman Ensemble in the 1980s, recording Synthesis (1986) and beginning a long-running duo and small-group collaboration with pianist Marilyn Crispell that produced Gaia (1988, a trio with Crispell and Doug James) and continued into a reunion festival performance in 2000. He also joined a collective quintet billed with Sonny Fortune, Billy Harper, Stanley Cowell, and Billy Hart on Great Friends (1987) and Such Great Friends (1991). Workman began teaching in this period as well, joining the faculty of the University of Michigan and, from 1987, The New School for Jazz and Contemporary Music in New York, where he has remained a longtime professor.

In 1987 Workman co-founded Trio 3, a collective avant-garde trio with saxophonist Oliver Lake and drummer Andrew Cyrille that has recorded steadily for three decades (sometimes expanded with a rotating pianist, including Geri Allen and Vijay Iyer), and he continued to lead his own dates: Images (recorded live at New York's Knitting Factory, Denon/Leo, 1989-90), Altered Spaces (Leo Records, 1993), Summit Conference (Postcards, 1994, with Andrew Hill, Sam Rivers, and Julian Priester), and Cerebral Caverns (Postcards, 1995, an unusually colored sextet with Geri Allen, Sam Rivers, Julian Priester, Elizabeth Panzer on harp, and Tapan Modak on tabla). Beginning in 1984 he also collaborated on multidisciplinary performance-art works with director and choreographer Maya Milenovic Workman, including "Ophelia's Ocean" and "Guernica Continuum." His honors include the Jazz Foundation of America's Life Achievement Award and the International Association of Jazz Educators' Citation of Excellence (both 1997), the Mid Atlantic Arts Foundation's Living Legacy Award (1999), a Living Legend citation from the African American Historical and Cultural Museum in his native Philadelphia, and the Eubie Blake Award.

Workman has continued recording and performing into his ninth decade, largely in trio and quartet settings alongside Andrew Cyrille: Reflections (TUM Records, 2004, with saxophonist Juhani Aaltonen) and Witch's Scream (TUM Records, 2006, with reedman John Tchicai). In 2020 he received an NEA Jazz Masters designation and, jointly with Maya Milenovic Workman, a Guggenheim Fellowship in music composition. In 2024 he recorded the quartet album Embracing the Unknown for Mahakala Music with saxophonists Ivo Perelman and Chad Fowler and Cyrille on drums. A new group, Trio Imagination, with pianist David Virelles and Cyrille, released Creative Inspirations in September 2026, and Workman remains active on the concert stage, including a documentary-linked performance piece at that October's BRIC JazzFest and an improvised collaboration with Wadada Leo Smith, Sylvie Courvoisier, Mary Halvorson, Nicole Mitchell, and Terri Lyne Carrington at the Kennedy Center.

Workman has long been rated among the most technically accomplished bassists in jazz, and among the most versatile: a player equally convincing driving hard bop's fast tempos in the Jazz Messengers and Blue Note's mainstream, and working entirely outside metric and harmonic convention in Archie Shepp's, Pharoah Sanders's, and his own free settings. His time feel and full, resonant tone made him a first-call studio bassist through the 1960s, while his standing association with Trio 3 and his own small-group leader dates place him among the defining bassists of the post-Coltrane avant-garde. His four-decade tenure at The New School has also made him one of jazz bass's most influential teachers.