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Guaraldi's first recording was made in November 1953 with Cal Tjader and came out early in 1954. The early 10 inch LP was called The Cal Tjader Trio, included "Chopsticks Mambo," "Vibra-Tharpe," and "Lullaby of the Leaves." By 1955, Guaraldi had his own trio with Eddie Duran and Dean Reilly. He then reunited with Cal Tjader in June, 1956 and was an integral part of two great bands that the vibraphonist assembled. The first band played mainly straight jazz and included Al Torre (drums), Eugene Wright (bass) and Luis Kant (congas and bongos). The second band was formed in the spring of 1958 and included Al McKibbon (bass), Mongo Santamaria (congas and bongos) and Willie Bobo (drums and timbales). Reed men Paul Horn and Jose "Chombo" Silva were also added to the group for certain live performances and recordings. He made a big splash with his performance with Tjader at the 1958 Monterey Jazz Festival.
Guaraldi left the group early in 1959 to pursue his own projects full time. He probably would have remained a well-respected but minor jazz figure had he not written an original number to fill out his covers of Antonio Carlos Jobim/Luis Bonfá tunes on his 1962 album, Jazz Impressions of Black Orpheus, inspired by the French/Brazilian film Black Orpheus, which won an Academy Award for Best Foreign Language Film. Fantasy released "Samba de Orpheus" as a single, trying to catch the building bossa nova wave, but it was destined to sink without a trace when radio DJs began flipping it over and playing the B-side, Guaraldi's "Cast Your Fate to the Wind." A gentle, likeable tune, it stood out from everything else on the airwaves, and became a grass-roots hit. It also won the grammy for Best Original Jazz Composition. While "Cast Your Fate To The Wind" by Guaraldi achieved modest chart success as a single in 1963, a cover version two years later by British group Sounds Orchestral cracked the Billboard top 10 (in the spring of 1965). Unlike many songwriters who grow weary of their biggest hits, Guaraldi never minded taking requests to play it when he appeared live. "It's like signing the back of a check," he once remarked.