Von Freeman’s first venture into the recording studio took place in 1954, backing a vocal group called The Maples for Al Benson’s Blue Lake label. He appeared on Andrew Hill’s second single on the Ping label in 1956, followed by some recording for Vee-Jay with Jimmy Witherspoon and Albert B. Smith in the late 1950s, and a recorded appearance at a Charlie Parker tribute concert in 1970.

In 1972, Freeman first recorded under his own name, the album Doin’ It Right Now with the support of Roland Kirk. His next effort was a marathon session in 1975 released over two albums by Nessa. After that he lived, regularly performed, and recorded in Chicago. His recordings included three albums with his son, the tenorist Chico Freeman, and You Talkin’ To Me with 22-year-old saxophonist Frank Catalano, following their successful appearance at the Chicago Jazz Festival in 1999.

One of Freeman’s contributions was his mentoring of countless younger musicians such as Corey Wilkes and Ben Paterson as well as his steadfast support of what he liked to call “hardcore jazz” (as he still did in a 2001 article in DownBeat.) Freeman’s quartet played Monday nights throughout the 1970s and the mid-1980s at The Enterprise Lounge which closed when he toured Japan, and then Tuesdays at The New Apartment Lounge with his longtime trio of sidemen composed of drummer Michael Raynor, guitarist Mike Allemana and bassist Matt Ferguson. The quartet played a long set first, the vehicle that showcased Freeman’s range from sensitively unwound ballads to intense improvisations that utilized his sometimes rough timbre and indefinite pitch to create a unique avant garde style of his own. His performances were also impressive verbal ones, as he served as an important figure that both helped African-American culture thrive on the South Side as well as invited the participation of European Americans and others into the warmth of the community he and the rest of the Enterprise and Apartment created.

Freeman was considered a founder of the “Chicago School” of jazz tenorists along with Gene Ammons, Johnny Griffin and Clifford Jordan. His music has been described as “wonderfully swinging and dramatic” featuring a “large rich sound”. “Vonski”, as he was known by his jazz fans, was selected to receive the nation’s highest jazz honor, the NEA Jazz Masters award. Freeman died of heart failure on August 11, 2012, in his home town, at the age of 88.