Kenny Drew was born in New York City in August of 1928. At the age of 5, he began studying classical piano with a private teacher and at 8, gave a recital. This early background is similar to that of Bud Powell, the man who later became his main inspiration as a jazz pianist. After digging Fats Waller, at 12, and then Art Tatum and Teddy Wilson, Drew attended the High School of Music and Art. He was known as a hot boogie woogie player but passed through this phase before graduation.
Kenny's first professional job was as accompanist at Pearl Primus' dance school. At the same time, he was alternating with Walter Bishop Jr. in a neighborhood band that included Sonny Rollins, Jackie McLean and Art Taylor. In this period, he used to hang-out on 52nd Street to listen to Charlie Parker and Powell and began sitting in at various jam sessions around town.
In January of 1950, Drew made his first appearance on record, with Blue Note. Howard McGhee was the leader and the other featured soloists were Brew Moore and J.J. Johnson. One of the six sides released was I'll Remember April. The label, in addition to stating Howard McGhee's All Stars, further read, Introducing Kenny Drew.
Later, in 1953, Kenny made his first album as a leader. Again it was Blue Note who recorded him, this time in a trio with Curly Russell and Art Blakey. But Kenny opted to settle in Los Angeles for the next few years. There in 1955, he formed a quartet with the late Joe Maini, Leroy Vinnegar and Lawrence Marable. The quartet first recorded together in 1955 for Pacific Jazz. In December, Jazz West, a subsidiary of Aladdin Records, brought the quartet as is into Capitol's recording studios for “Talkin' & Walkin'.”