Pianist Wynton Kelly played on Kind of Blue, the best-selling jazz album in history, was described by peers as the greatest supporting musician in the genre, and had trumpeter Wynton Marsalis named in his honor, yet he died at 39 in a Toronto hotel room with almost no money. Born in Brooklyn in 1931 to Jamaican immigrant parents, he started piano at four, was forced by his vocational high school to study upright bass and theory instead, played organ in churches and with R&B groups as a young teen, and at 16 made his recording debut on Hal Singer’s chart-topping “Cornbread.”

This deep dive follows his 1952 Army draft, where he and Duke Pearson lobbied to integrate a segregated entertainment unit and he became a musical director and arranger, his emergence as the most in-demand sideman of the mid-1950s, and the night Miles Davis told a late-arriving Red Garland, “Wynton’s got the gig.” It explains why Kelly plays only on “Freddie Freeloader” on the otherwise Bill Evans-centered Kind of Blue, breaks down his block chords and dotted-eighth-note swing, and covers the Wynton Kelly Trio with Jimmy Cobb and Paul Chambers, their work behind Wes Montgomery, his onstage denture gag, his epilepsy and heavy drinking, and his sudden death in 1971.

• How forced bass training paid off when Paul Chambers fell asleep in an Abbey Lincoln session
• The R&B dance-hall roots of his “happy sound”
• Philly Joe Jones on Kelly laying “a beautiful arrangement of flowers” behind soloists
• The trampoline, not the brick wall: what block chords and dotted eighth notes actually do
• Why the industry typecast him as a sideman, and what a main-character culture loses without glue guys