Influenced by the nascent bebop movement, Roland put together his own ensembles late in the decade, and in the 1950s he played with Oscar Pettiford (1951), George Shearing (1951–1953), Howard McGhee, and Artie Shaw and his Gramercy Five (1953–1954), Freddie Redd (1955), Mat Mathews (1956), and Aaron Sachs (1956).

During his 13-year "gig" at Monty Trainer's Bayshore Restaurant in Coconut Grove, he was credited for having trained many young musicians from the University of Miami.

He worked steadfastly throughout his life in local clubs accompanied by bassists such as Lew Berryman and Mark Trail, and singers like Sandy Patton.

Roland's contributions can be appreciated in a quote from Peter Dempsy regarding Artie Shaw's Summit Ridge Drive album: "The Gramercy Five recordings of 1953 and 1954 document a brilliant phase in early modern jazz, manifested in the presence of pianist Hank Jones, guitarist Tal Farlow, bassist Tommy Potter and vibraphonist Joe Roland.

His Website http://www.bobbyroland.com/Joe_Roland.html has a page dedicated to Joe Roland with additional history and pictures with other Jazz greats.