He liked Oscar Peterson, the Buddy Rich Big Band, George Gershwin, and the Latin music he heard while growing up in Miami.
He studied privately with classical composer David Del Tredici and jazz pianist John Lewis.
[9] During the next ten years, Chesky made a living writing music for TV movies and commercials, continuing to learn from older composers.
[15] In 1986 Chesky visited the classical pianist Earl Wild, a friend of an uncle, to learn more about writing music.
[11] Chesky albums are recorded live, sometimes in churches, often with custom-made equipment, and don't undergo post-recording polishing, overdubbing, and mixing.
This arrangement reflects David Chesky's desire to make albums that approximate the original performance.
Chesky has won two Independent Music Awards, both for best Contemporary Classical Album: String Theory (2011) and Rap Symphony (2014).