Don Rickles was just another little known comic working a small club in Miami Beach in the 1950s when Frank Sinatra came in with his entourage.

Using insult as his weapon of choice and a quick, knowing smirk as his defense, Rickles delighted audiences from sold-out Vegas showrooms to late-night TV to Hollywood roasts with a brand of aggressively caustic humor that targeted everyone from unknown “Hockey pucks” to big-name celebrities.

Age didn’t seem to slow Rickles or mellow his humor, as a Las Vegas Review-Journal reporter discovered during a Rickles performance in 1998 at the Desert Inn when the “King of Zing” was 72.

As a writer for the New Yorker put it in a 2004 profile of the comedian, “Is certainly to be credited with taking insult comedy to an unprecedented level of ferocity.” And, in so doing, few comedians matched Rickles’ longevity.

He starred in “The Don Rickles Show,” a short-lived, 1968-69 comedy-variety show.

He made two attempts as a sitcom star: playing a New York advertising agency executive in “The Don Rickles Show” and a Navy chief petty officer in “C.P.O. Sharkey”.