Initially, Freeman was classically trained. His reputation as a jazz pianist grew in the 1940s after working with Art Pepper and Shorty Rogers. He played with Charlie Parker on the 1947 “Home Cooking” jazz session. Numerous collaborations followed in the 1950s with Chet Baker, Shelly Manne, and Art Pepper. These collaborations included the Jazz Immortal CD recorded with Russ Freeman and jazz trumpeter Clifford Brown in 1954, which included leading musicians Brown and Zoot Sims. On the Jazz Immortal CD, Russ Freeman was able to play in a combo that recorded many Clifford Brown compositions.