1955–1958: the first great Miles Davis Quintet

Garland became famous in 1955 when he joined the Miles Davis Quintet, featuring John Coltrane, Philly Joe Jones, and Paul Chambers. Davis was a fan of boxing and was impressed that Garland had boxed earlier in his life. Together, the group recorded their famous Prestige albums, Miles: The New Miles Davis Quintet (1956), Workin, Steamin', Cookin', and Relaxin'. Garland's style is prominent in these seminal recordings—evident in his distinctive chord voicings, his sophisticated accompaniment, and his musical references to Ahmad Jamal's style. Some observers dismissed Garland as a "cocktail" pianist,^[5] but Miles was pleased with his style, having urged Garland to absorb some of Jamal's lightness of touch and harmonics within his own approach.^[6]

Garland played on the first of Davis's many Columbia recordings, 'Round About Midnight (1957). Their relationship was already beginning to deteriorate, but he continued playing with Miles. By 1958, Garland and Jones had started to become more erratic in turning up for recordings and shows. He was eventually fired by Miles but later returned to play on another jazz classic, Milestones. Davis was displeased when Garland quoted Davis's much earlier, and by then famous, solo from "Now's The Time" in block chords during the slower take of "Straight, No Chaser". Garland walked out of one of the sessions for Milestones; on the track "Sid's Ahead", Davis comped behind the saxophone solos in his absence.

1958–1984: Red Garland Trio and later life

In 1958, Garland formed his own trio. Among the musicians the trio recorded with are Pepper Adams, Nat Adderley, Ray Barretto, Kenny Burrell, Eddie "Lockjaw" Davis, Jimmy Heath, Harold Land, Philly Joe Jones, Blue Mitchell, Ira Sullivan, and Leroy Vinnegar. The trio also recorded as a quintet with John Coltrane and Donald Byrd.^[7] Altogether, Garland led 19 recording sessions while at Prestige Records and 25 sessions for Fantasy Records. He stopped playing professionally for a number of years in the 1960s when the popularity of rock music coincided with a substantial drop in the popularity of jazz.

Garland eventually returned to his native Texas in the 1970s to care for his aged mother. He led a recording in 1977, named Crossings, which reunited him with Philly Joe Jones, and he teamed up with bassist Ron Carter. His later work tended to sound more modern and less polished than his better-known recordings. He continued recording until his death from a heart attack on April 23, 1984, at the age of 60.^[8]

As leader

Compilations

• Rediscovered Masters (Prestige, 1977) – rec. 1958–61
• At the Prelude, Vol. 1 (Prestige, 1994) – rec. 1959. compilation of Red Garland at the Prelude + Red Garland Live!.
• Blues in the Night (Prestige, 1997) – rec. 1960. compilation of Halleloo-Y'-All + Soul Burnin'.
• Red's Blues (Prestige, 1998) – rec. 1956–62.
• Stretching Out (Prestige, 2002) – rec. 1959. compilation of Satin Doll + Lil' Darlin'.
• The Best of the Red Garland Quintets (Prestige, 2004)
• The Best of the Red Garland Trios (Prestige, 2004)

As sideman