He played with many of the name bands of the swing era and accompanied some of the music industry's most noted vocalists He is remembered today as an early and important influence on the great jazz pianist Bill Evans.

Bill was introduced to the music of Fletcher Henderson and Duke Ellington in his high school years and began to ponder a career as a professional musician.

After graduating, he became the pianist in The Cliff McKay Band, a Canadian group that played a few "hot" arrangements amongst its stylistically broad program.

For several years, beginning in the late 1940s, Clifton alternated solo shows with the great pianist, Cy Walter (the Park Avenue Art Tatum) at New York's famed Drake Room.

[9] Later work included an album featuring Clifton's talents as an arranger and conductor as well as pianist for the Ilene Woods LP "It's Late".