While working in a
Rickles earned the nicknames "The Merchant of Venom" and "Mr. Warmth" for his poking fun at people of all ethnicities and walks of life. When he was introduced to an audience or on a television talk show, Spanish matador music, "La Virgen de la Macarena", would usually be played, subtly foreshadowing someone was about to be metaphorically gored. Rickles said, "I always pictured myself facing the audience as the matador."
In 1958, Rickles made his film debut in a serious part in Run Silent, Run Deep with Clark Gable and Burt Lancaster. Throughout the 1960s, he often appeared on television in sitcoms and dramatic series. Rickles guest-starred in Get Smart as Sid, an old war buddy of Max who comes to stay with him. In an episode of the 1960s drama series Run for Your Life, Rickles played a distressed comedian whose act culminates when he strangles a patron while imploring the patron to "Laugh!" Rickles took a dramatic turn in the low-budget Roger Corman film X: The Man with the X-Ray Eyes as a carnival barker out to exploit the title character (played by Ray Milland).
Rickles appeared in the popular Beach Party film series. He recalled in his 2007 memoir that at a White House dinner, Barbara Bush teased him about his decision to appear in those films. Rickles' agent, Jack Gilardi, was married to Annette Funicello when Rickles was cast in the Beach Party films. He subsequently began appearing more frequently on television talk shows, first appearing on The Tonight Show Starring Johnny Carson in 1965.
He became a frequent guest and guest host, appearing more than 100 times on The Tonight Show during
In 1968, Rickles released a live comedy album, Hello, Dummy!, which reached #54 on The Billboard 200 album chart. The same year he starred in his own variety show on ABC, The Don Rickles Show, with comedy writer Pat McCormick as his sidekick. The show lasted one season. During the 1960s, Rickles made guest appearances on The Dick Van Dyke Show, The Munsters, The Addams Family, The Mothers-in-Law, Gilligan's Island, Get Smart, The Andy Griffith Show and I Dream of Jeannie.