Reilly was known for his friendly spirit, and his history running music clubs began in the 1950s, the Globe reported. Born in 1918, Reilly served in the Army Air Forces during World War II and was called back into service during the Korean War, when he was stationed as a club officer at Otis Air Base in Falmouth.
At the end of the war, he ran a bar in Falmouth for a few years before moving to manage Club Casablanca in Cambridge's Harvard Square. He and a partner later bought a bar on Massachusetts Avenue in Cambridge, which they named Jacks, and Reilly began bringing in musical acts.
In the late 1970s, Reilly opened Ryles and continued to invite musicians of all walks to play, ranging from famous names to Berklee students looking to play their first gigs. He sold Ryles in the late '90s.