PANAMA CITY, Fla. — Renowned jazz clarinetist Buddy DeFranco – who collaborated with Frank Sinatra, Billie Holiday and other top singers and musicians of his era – has died at the age of 91, his family said Friday.

DeFranco’s family told The Associated Press that the famed musician died Wednesday evening at a Panama City hospital.

DeFranco’s wife, Joyce, said he had been in declining health in recent years. The couple lived in Panama City.

DeFranco, a member of the American Jazz Hall of Fame, performed at venues around the world for 75 years and recorded with musicians including Sinatra, Holliday, Art Tatum, Ella Fitzgerald and Tony Bennett. He conducted the Glenn Miller Orchestra from 1966 to 1974.

“Buddy DeFranco almost single-handedly was the clarinetist who moved the harmonic and rhythmic language forward from where Benny Goodman left off into the much more adventurous territory of bebop and beyond, while never forgetting his roots in swing music. He was also unfailingly kind and supportive to every other clarinetist who came after him,” said leading jazz clarinetist Ken Peplowski.

DeFranco was named a National Endowment for the Arts Jazz Master, and named a Living Jazz Legend in a Kennedy Center ceremony.

DeFranco was recognized 16 times with the Playboy All-Star award for top jazz clarinetist in the world.