[6] 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.

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 Steve Coleman, 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.

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.

[8] Freeman was considered a founder of the "Chicago School" of jazz tenorists along with Gene Ammons, Johnny Griffin and Clifford Jordan.