Buddy DeFranco, onetime bandleader of the Glenn Miller Orchestra who played clarinet with Frank Sinatra, Billie Holiday and many others, died Wednesday in Panama City, Fla. He was 91.

One of the few bebop clarinet players, he was honored as the top jazz clarinetist in the world 16 times with the Playboy All-Star Award. During his early days of performing, he played with Count Basie’s Septet, and led small combos with pianist Sonny Clark and guitarist Tal Farlow, recording for MGM Records, Norgran and Verve.

Though the heyday of big band music was long past, he kept the genre alive, leading Glenn Miller’s orchestra from 1966 to 1974. DeFranco performed with Ella Fitzgerald, Tony Bennett, Gene Krupa, Charlie Barnet, Art Tatum and Oscar Peterson.

DeFranco’s performanced last when he was 89. He was named a National Endowment for the Arts Jazz Master as well as a Living Jazz Legend at the Kennedy Center.

He is survived by his wife Joyce.