Born in 1956 in Miami, Chesky started taking piano lessons at age five and developed an interest in jazz and classical music. Along with listening to pianist Oscar Peterson and the Buddy Rich Big Band, Chesky also drew early inspiration from Latin music, Brazilian bossa nova, and show tunes. By the mid-'70s, while still a teenager, he had moved to New York City to pursue his music career. He studied privately there with classical composer David Del Tredici and pianist John Lewis of the Modern Jazz Quartet. In 1978, he formed a fusion-oriented big band that included players like saxophonist Michael Brecker, trumpeter Randy Brecker, and keyboardist Bob James. Chesky and his big band made their debut with 1980's Rush Hour on Columbia.
Also during this period, Chesky moved into classical composing; his pieces were performed by the London Symphony Orchestra, the Chicago Symphony Orchestra, and others. By 1987, he and his brother had founded the audiophile-friendly Chesky Records, concentrating on jazz, European classical, and Latin music. With David Chesky often working as producer, the label has released albums by a bevy of esteemed performers, including Phil Woods, Lee Konitz, Clark Terry, Paquito D'Rivera, McCoy Tyner, Tom Harrell, John Pizzarelli, and Fred Hersch. The label has also focused on vocal jazz and traditional pop, putting out albums by Peggy Lee, LaVerne Butler, Christy Baron, and Rebecca Pidgeon. In addition, there have been albums by Brazilian artists like Ana Caram, Badi Assad, Leny Andrade, and Luiz Bonfá.
As a solo artist, David Chesky also recorded for his own label, beginning with 1989's Club de Sol and 1990's The New York Chorinhos, the latter of which was a set of piano/guitar duets with Brazilian guitarist Romero Lubambo. He reunited with Lubambo for 1992's The Tangos and Dances, and followed with such varied recordings as 1996's solo piano date The Fantasies, 1997's 3 Psalms for String Orchestra, and 1998's Snowbears of Lake Louise.
More works followed in the 2000s, including The Agnostic, a collaboration with conductor Stephanie Gregory and the Slovak Philharmonic Orchestra Chorus. In 2007, Chesky worked with the Symphony Orchestra of Norrlands for Urban Concertos, which earned a Grammy nomination for Best Classical Contemporary Composition. He returned to a similar theme with 2011's David Chesky: Urbanicity; Concerto for Electric Guitar and Orchestra; The New York Variations. Jazz in the New Harmonic arrived in 2013 and found Chesky leading a quintet featuring Jeremy Pelt, Javon Jackson, Billy Drummond, and Peter Washington. A follow-up, Jazz in the New Harmonic: Primal Scream, arrived in 2015. He returned to classical that year with Joy Sorrow, featuring the Chelsea Symphony, and again showcased his large-ensemble skills with 2016's Orchestra of the 21st Century: The Venetian Concertos. A spin-off of his jazz group with Drummond and Washington released Trio in the New Harmonic: Aural Paintings in 2018, followed a year later by España, a concerto for two guitars and orchestra. In 2021, Chesky released another large-ensemble production, Songs for a Broken World, which featured contributions by Ute Lemper, Milan Milisavljevic, J'Nai Bridges, and others. ~ Matt Collar, Rovi