According to Peter Watrous, writing in The New York Times: "Mr. Redd hung out at jam sessions in the 1950s and played with many of the major figures, Sonny Rollins to Art Blakey, and worked regularly with Charles Mingus.

[4][5] Redd's most successful project was in the late 1950s when he was invited to compose the music for The Living Theatre's New York stage production of The Connection, which was also used in the subsequent 1961 film.

The theater production was a modest hit and the troupe toured the United States and Europe, performing in New York City, London, and Paris.

[6] Redd's success in the theater production, however, did not advance his career in the United States, and shortly afterwards he moved to Europe, spending time in Denmark and France.

[7] In the 60s, Redd spent time traveling to various regions such as Copenhagen, Amsterdam, Paris, London, Pittsburgh, San Francisco, Los Angeles, Guadalajara, Baltimore, and Carrboro.

[9] Redd returned to New York in 1949 after his enlistment ended, where he played with various artists such as Gene Ammons, Sonny Rollins, and Art Farmer.

Upon discharge, he worked with drummer Johnny Mills, and then in New York played with Tiny Grimes, Cootie Williams, Oscar Pettiford and the Jive Bombers.

This led him to move to Greenwich Village, where he continued with his music career in a loft alongside visual artists and poets since he was not allowed to perform in clubs without his card.

He eventually introduced Redd to author Jack Gelber, who played a major role in the creation of his biggest accomplishment from The Connection.

[10][7] Redd originally recorded enough material for an album in 1961, however, the tapes were put away once he had a conflict with one of Blue Note’s founders, Alfred Lion.

[8] Redd struggled to establish himself commercially; however, musically, his creative lines, particular voicings and innovative compositions solidified his reputation; he worked with such musicians as Jackie McLean, Tina Brooks, Paul Chambers, Howard McGhee, Milt Hinton, Lou Donaldson, Benny Bailey, Charles Mingus, Louis Hayes, Al McKibbon, Billy Higgins, Osie Johnson, Tommy Potter, and Joe Chambers, among others.

Redd completed a European tour in 2013, and two albums he made that year – Reminiscing and (with Butch Warren) Baltimore Jazz Loft were issued in February 2021.