[1] Beginning his writing career as a newspaper reporter in his native Canada, between 1948 and 1955 Lees contributed to The Hamilton Spectator, the Toronto Telegram, and the Montreal Star, and first worked as a music critic in the United States for the Louisville (Kentucky) Times between 1955 and 1959 and was editor of the jazz magazine Down Beat between 1959 and 1962.
[2] Lees wrote nearly one hundred liner notes for artists as diverse as Stan Getz, John Coltrane, George Barnes (musician), and Quincy Jones.
[2] Lees wrote a rhyming dictionary in the 1980s, and published three compilations of pieces from his Jazzletter: Singers and the Song (1987), Meet Me at Jim & Andy's (1988), and Waiting for Dizzy (1991).
[2] Lees studied composition by correspondence with the Berklee College of Music, in the early 1960s and piano with Tony Aless and guitar with Oscar Castro-Neves in New York City.
Lees contributed lyrics to "Bridges" by Milton Nascimento; "Yesterday I Heard the Rain" by Armando Manzanero; and Bill Evans' "Waltz for Debby".
Poems by Pope John Paul II were translated by Lees and recorded by Sarah Vaughan as part of a song cycle on her album The Planet Is Alive...Let it Live!