Obed Calvaire was born in 1982 in Miami, Florida, to Haitian parents, and grew up inside the Haitian Protestant church culture of South Florida rather than around records. His parents kept television and mainstream pop out of the house; what he heard instead was Haitian radio and the music of marathon "40 Days and 40 Nights" revival meetings, where he first sat down at a kit because the scheduled drummer had not turned up. He kept the chair. Two of the musicians he met at those revivals, the keyboardist Harold St. Louis and the bassist Addi Lafosse, went on to the same middle school and are still playing with him today. His paternal grandfather was a Vodou priest and his maternal grandmother took part in the same religion, a family inheritance that sat alongside, rather than inside, the austere Protestant home he was raised in. He attended the New World School of the Arts, the Miami-Dade public high school for artistically gifted students.

He went north to the Manhattan School of Music and finished the undergraduate course in three years, taking his bachelor of music in 2003 and a master of music in jazz drum set in 2005, studying in the drum studio of John Riley. New York work started before either degree was finished. From 2002 to 2004 he held the chair in the Steve Turre Sextet, and by the mid-2000s he was a regular in the city's large-ensemble economy: the Vanguard Jazz Orchestra, the Mingus Big Band, the Bob Mintzer Big Band, the Roy Hargrove Big Band, the Metropole Orkest in the Netherlands, and the Clayton Brothers Quintet co-led by John Clayton and his brother Jeff.

His recorded work through that decade tracks the same trajectory. He is on Aaron Parks's early Keynote sessions The Wizard (2001) and Shadows (2002), on the trumpeter Philip Dizack's Beyond a Dream (2005, Fresh Sound New Talent), and on the Haitian singer Emeline Michel's Rasin Kreyol (2004). 2008 was a dense year: he cut Live at Louis 649 (Anzic Records) with the Israeli saxophonist Eli Degibri and the organist Gary Versace in an organ trio, recorded two nights at Smalls with the David Kikoski Trio for SmallsLIVE, and played on the bassist Linda Oh's self-released debut Entry. He also joined the Trinidadian trumpeter Etienne Charles's band around Folklore (2009) and stayed through Kaiso (2011), Creole Soul (2013), Creole Christmas (2015), Carnival (2019) and the Creole Orchestra project of 2024.

From 2013 to 2021 he held the drum chair of the SFJAZZ Collective, the San Francisco octet that commissions a new piece from each member every season alongside a program devoted to one modern composer. He is on the Collective's annual live sets across that whole span, from The Music of Chick Corea (2013) through the Joe Henderson, Michael Jackson, Miles Davis, Thelonious Monk and Antonio Carlos Jobim programs, playing beside Miguel Zenón, Matt Penman, Avishai Cohen, Edward Simon, David Sánchez, Robin Eubanks, Stefon Harris and Warren Wolf. The same years brought the violinist Zach Brock's Criss Cross records Purple Sounds (2014) and Serendipity (2015), David Binney's Anacapa (2014), Helen Sung's Anthem for a New Day (2014) and a long run with Monty Alexander, including Harlem-Kingston Express Live! and Wareika Hill: Rasta-Monk Vibrations.

In 2021 he took the drum chair of the Jazz at Lincoln Center Orchestra under Wynton Marsalis, succeeding Ali Jackson in a rhythm section with pianist Dan Nimmer and bassist Carlos Henriquez. He had already recorded The Democracy! Suite with a JLCO septet in 2020, released on Blue Engine Records in January 2021, and the band's subsequent Blue Engine catalogue with him in the chair includes Big Band Holidays III (2023), Freedom, Justice and Hope (2024) and The Shanghai Suite (2024). In January 2024 he music-directed and produced the orchestra's Max Roach centennial concerts at Frederick P. Rose Hall, two nights on 19 and 20 January that Blue Engine issued that August as The Music of Max Roach. Every piece on it is a Roach original recorded between 1957 and 1966 except one: Calvaire's own "Between Max and Ti-Roro," which sets Roach beside Ti-Roro, the Haitian drummer of roughly the same generation.

Parallel to the orchestra he has kept a working small-group life. Dave Holland brought him into a trio with guitarist Kevin Eubanks for Another Land, recorded at Sear Sound in New York on 10 and 11 September 2019 and released by Edition Records in 2021, on which Calvaire contributes one composition. Nine months into the pandemic he cut Whole Lotta Love: The Music of Led Zeppelin for Chesky Records in a single day, 16 December 2020, with saxophonist Bob Franceschini, pianist Kevin Hays and bassist Orlando Le Fleming. His debut as a leader arrived on 12 April 2024: 150 Million Gold Francs (Ropeadope), named for the indemnity France extorted from Haiti at gunpoint after the Haitian Revolution, with a band drawn largely from Haitian and Haitian-American musicians including alto saxophonist Godwin Louis, pianist Sullivan Fortner, guitarist Dener Ceide, and the two childhood friends from those Miami revivals, Harold St. Louis and Addi Lafosse. He remains on the road with the JLCO and continues to record widely as a sideman, most recently on Ben Wendel's Understory: Live at the Village Vanguard (2024) with Gerald Clayton and Linda May Han Oh.

Calvaire's distinguishing skill is that he plays Haitian ceremonial rhythm on a jazz drum kit as a single player, covering parts that in their original setting are divided among several hand drummers, and he does it without overdubbing. Reviewing 150 Million Gold Francs for The Rhythm of Study, the saxophonist and jazz-studies scholar Benjamin Barson picked out his yanvalou pattern on cowbell over an active bass drum and snare on "Haiti's Journey," and the catá-derived groove under the album's opening track, where a five-beat ceremonial grouping stretches across a written 4/4. Calvaire's own account of that elasticity is characteristically technical: "In ceremonies, the catá extends in 5. Groupings of 4 that can be elastic in 5." Compas, catá, yanvalou and the processional rara form all sit inside the same records as swing and post-bop time, which is what makes the Haitian material read as vocabulary rather than as decoration. On the big-band side the reference point he names himself is Max Roach, whose centennial concerts he directed: "You could take four bars from Max and come up with a lifetime of vocabulary on the instrument. That's how much he's influenced our music." The title he gave the one original in that program, "Between Max and Ti-Roro," states the two halves of his playing in four words.