Don Rickles first film, Run Silent Run Deep, was released in 1958 and Rickles finally acted with the big stars. Clark Gable starred in the film. Critics and audiences appreciated Rickles? work and he was soon cast in another film. He received much praise from critics for his villainous performance in The Rat Race, released in 1960. He also began making regular appearances on such TV series as The Thin Man and The Twilight Zone.

He began to be type cast as the short, bald, slightly evil character in all of his film roles. Though he was a good character actor, the parts came few and far between. Rickles decided to try his luck as a stand-up comic. He began developing an act and trying it out at local nightclubs. He began with a traditional act with one bit tying into the next. But one performance changed all that. During the show a few audience members began heckling Rickles. Instinctively Rickles lashed out with sharp-tongued insults. The audience cracked up. The impromptu insults got more laughs than any of his prepared material. Rickles had finally found his niche. From that day on his trademark was picking out audience members for a taunting.

Rumor has it that Frank Sinatra walked into one of Rickles performances. After a moment of awe, Rickles settled into a string of insults directed at the famous singer. Sinatra loved it. He was laughing so hard that he fell out of his chair. From that point on, stars flocked to Rickles? shows to be the target of his quick wit. He hit many famous nightclubs in New York and Los Angeles and catered to many famous audience members. Rickles has never been concerned with political correctness and that disregard for social normalcy helped further his career.

Rickles continued television and film appearances during his concentrated nightclub circuit. He made guest appearances on television programs like F Troop, The Andy Griffith Show, The Dick Van Dyke Show, I Spy, and Run for Your Life. He also appeared as himself on variety shows like The Dean Martin Show and The Andy Williams Show. When the Dean Martin Show turned to a ?roast? format, Rickles became a regular. They could always count on his biting sense of humor to rough the audience up. Rickles had to take a little of his own medicine in 1974 when he was elected the Entertainer of the Year by the Friar?s Club.