Rickles took his first step toward national fame in 1957, when Frank Sinatra wandered in to the small Hollywood nightclub where Rickles was performing. The still-unknown Rickles eyed Sinatra and said, “I just saw your movie, The Pride and the Passion, and I want to tell you, the cannon’s acting was great. And, make yourself at home, Frank. Hit somebody.” Sinatra doubled up laughing and became one of Rickles’ biggest boosters among Hollywood celebrities. He soon became the “in” comic among the Hollywood stars, who flocked to his nightclub engagements to become the targets of his “insults.”

As a star-struck kid in New York City, Rickles aspired to share the Big Screen with such idols as Clark Gable and James Cagney. He got his wish in 1958, when he appeared in his first film, Run Silent Run Deep, starring Clark Gable. Rickles went on to receive critical praise for his villainous performance in Rat Race in 1960.

During a long period between acting assignments, Rickles decided to try stand-up comedy at a few clubs. Audiences laughed harder at his impromptu insults than at his prepared material, and Rickles’ legend as the king of insult comics was born.

In addition to his stand-up career, Rickles starred in numerous films and television shows over the decades, including Casino, Kelly’s Heroes, Gilligan’s Island, The Andy Griffith Show, Get Smart, Toy Story 1 and 2, and, most recently, the CBS hit series The Unit. Rickles won two Primetime Emmys including the 2008 HBO special entitled Mr. Warmth: The Don Rickles Project for the Best Individual Performance in a Variety or Musical.