Cuscuna played drums, saxophone and flute while young, but placed his emphasis on starting his own record label. He had a jazz show on WXPN and worked for ESP-Disk late in the 1960s, in addition to writing for Jazz & Pop Magazine and Down Beat. He moved from WXPN to WMMR in 1970, then onto WABC-FM (now WPLJ) as a progressive rock DJ at both stations. He took a position as a producer with Atlantic Records in the 1970s, recording Dave Brubeck and the Art Ensemble of Chicago. Not forgetting his popular music interests, in the early 1970s he also produced albums by Bonnie Raitt (Give It Up) and Chris Smither. He also worked at Motown, ABC (doing reissues of Impulse! albums), Arista, Muse, Freedom, Elektra and Novus. From 1975 to 1981 he went through the Blue Note archives and recovered many sessions which are now prized.
Along with Charlie Lourie, he founded Mosaic Records in 1983 specializing in jazz reissue box sets, with almost 200 releases as of 2009. Artists surveyed include highly visible masters like Thelonious Monk, Miles Davis, and Nat "King" Cole, and lesser known artists such as Tina Brooks and Ike Quebec. Cuscuna has won three Grammy Awards for his releases. Since 1984, Cuscuna has been a special consultant, producer, and reissue director of Blue Note Records.
- 1992: Best Historical Album for Nat King Cole, The Complete Capitol Trio Recordings
- 1998: Best Album Notes for Miles Davis, Miles Davis Quintet, 1965–68: The Complete Columbia Studio Recordings (with Bob Belden and Todd Coolman)
- 2001: Best Historical Album for Billie Holiday, Lady Day: The Complete Billie Holiday on Columbia (1933–1944) (with Michael Brooks)
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