The early to mid-'80s found Chesky doing a lot of classical composing; his pieces were performed by the London Symphony Orchestra, the Chicago Symphony Orchestra, and others. By 1987, David Chesky and his brother were running Chesky Records, an audiophile-friendly company that has concentrated on jazz, European classical, and Latin music. The list of artists that Chesky Records recorded since the late '80s is a long one; Phil Woods, Lee Konitz, Clark Terry, Paquito D'Rivera, McCoy Tyner, Tom Harrell, John Pizzarelli, Red Rodney, Fred Hersch, and Johnny Frigo are among the well-known jazz instrumentalists who David Chesky has worked with as a producer for Chesky Records. The label has dabbled in vocal jazz and traditional pop, putting out CDs by Peggy Lee, LaVerne Butler, Christy Baron, and Rebecca Pidgeon; and the company has recorded Brazilian artists like Ana Caram, Badi Assad, Leny Andrade, and the late Luiz Bonfá. The first album that David Chesky recorded for Chesky Records was 1989's Club de Sol, which was followed by 1990's The New York Chorinhos (an album of piano/guitar duets with Brazilian guitarist Romero Lumbambo). The pianist was reunited with Lumbambo in 1992, when they recorded The Tangos and Dances for Chesky Records. David Chesky's subsequent albums for that label included 1996's The Fantasies, 1997's 3 Psalms for String Orchestra, and 1998's Snowbears of Lake Louise.