[4] Littlefield was regarded as a teenage wonder and overnight sensation when in 1949, at the age of 18, he popularized the triplet piano style on his Modern Records debut single, "It's Midnight".

[4] Other major influences on Littlefield's style were the Texas musicians Charles Brown and Amos Milburn.

[7] He became a major nightclub attraction and recorded with West Coast musicians such as Maxwell Davis.

[8][user-generated source] In 1951, his duet with Little Lora Wiggins, "I've Been Lost", reached number 10 on the R&B chart.

His first session for Federal produced "K. C. Loving", written by Jerry Leiber and Mike Stoller and later re-recorded by Wilbert Harrison as "Kansas City".