After toiling in relative obscurity for years as a more conventional stand-up comedian, Rickles unwittingly discovered his biggest laughs came when he turned the table on his hecklers. His career then skyrocketed after he insulted the hot-tempered Sinatra, who normally did not take kindly to such treatment.
When the superstar singer and actor walked into a Hollywood club in 1957 where Rickles was performing, the comedian greeted the “Chairman of the Board” from the stage: “Make yourself at home Frank. Hit somebody.” Sinatra roared — with laughter.
With Sinatra’s endorsement, Rickles began his comedic assault on people famous and not so famous — Jews, Asians, African Americans, the Irish, Puerto Ricans, red-headed women, short guys, you name it — with tremendous results. He referred to stupid people as “hockey pucks,” and in 1959, he signed for his first Las Vegas appearance, in the lounge of the Hotel Sahara.
In 1985, when Sinatra was asked to perform at Ronald Reagan’s second Inaugural Ball, he insisted that Rickles accompany him for a comedy routine. Rickles, naturally, did not spare the president (“Am I going too fast for you, Ronnie?” he asked) and considered that performance among the highlights of his career.
Rickles was still going strong in June 2012 when, during the American Film Institute’s tribute to actress Shirley MacLaine, he joked that he “shouldn’t make fun of the blacks. President Obama is a personal friend of mine. He was over to the house yesterday, but the mop broke.”
Rickles honed his reputation in numerous appearances on The Dean Martin Celebrity Roasts that ran on NBC from the mid-1970s to the mid-80s. The specials provided a perfect venue for Rickles to unleash his caustic brand of humor on such visiting dignitaries as Sinatra, Reagan, Bob Hope, Lucille Ball, Kirk Douglas, Sammy Davis Jr. and Mr. T.
Johnny Carson provided Rickles a late-night stage by making him one of The Tonight Show’s most-frequent guests. On one memorable moment in 1968, Rickles cozied up to a half-naked Carson during a sketch with two Japanese female masseuses and said, “I’m so lonely, Johnny!” Carson threw him in a bathtub. More recently, he was a regular guest on Late Show With David Letterman, in which the CBS host treated Rickles like royalty.
Rickles intermittently played in movies, highlighted by Kelly’s Heroes (1970), where he co-starred with Clint Eastwood as Sgt. Crapgame, an Army black-marketer who had no compunction about cutting favorable deals with the Nazis.
He also played opposite beach bunny Annette Funicello in such movies as Pajama Party (1964) and Beach Blanket Bingo (1965), appeared as a Vegas slime-ball in Martin Scorsese’s Casino (1975) and voiced the cranky Mr. Potato Head in the Toy Story films.
Donald Jay Rickles was born in the New York borough of Queens on May 8, 1926. Following high school, he served in the U.S. Navy during World War II, then studied acting and graduated from the American Academy of Dramatic Arts. At age 32, Rickles landed a small part in Robert Wise’s submarine drama Run Silent, Run Deep (1958), starring Clark Gable. Two years later, he was cast in The Rat Race with Tony Curtis and Debbie Reynolds.
Not surprisingly, Rickles found there weren’t many leading roles for a paunchy 5-foot-6 balding man. So, he worked up a nightclub act. After his Sinatra encounter, he perfected his bite and would land gigs in all the Vegas hotels: the Riviera, the Golden Nugget, the Desert Inn and the Sahara. Rickles would come onstage accompanied by the old Spanish bullfight song “La Virgen de la Macarena,” a subtle signal that someone was about to be metaphorically gored.
Flush with his casino successes, Rickles cut two best-selling comedy albums in the ’60s: Hello, Dummy! and Don Rickles Speaks.
Success as a star of his own TV series eluded him. He played Naval Petty Officer Otto Sharkey in NBC’s CPO Sharkey, which ran from 1976-78, and a used car salesman and father of Richard Lewis in Daddy Dearest, quickly canceled by Fox in 1993. He had two series titled The Don Rickles Show; each ran a handful of episodes. For one season in the ’80s, he hosted ABC’s Foul-Ups, Bleeps & Blunders with singer Steve Lawrence.
Rickles’ TV guest appearances include episodes of The Twilight Zone, Wagon Train, Burke’s Law, The Dick Van Dyke Show, The Beverly Hillbillies, Gomer Pyle, U.S.M.C., I Dream of Jeannie, I Spy, Get Smart (alongside his buddy, Don Adams), Rowan & Martin’s Laugh-In, Sanford and Son, The Bernie Mac Show and Hot in Cleveland.
In 1965, Rickles married Barbara Sklar, who survives him. The couple, who often vacationed with deadpan comic Bob Newhart and his wife, Virginia, had two children, Mindy and Larry. His son, who produced the HBO documentary Mr. Warmth: The Don Rickles Project, died in December 2011 at age 41.
This article originally appeared on The Hollywood Reporter.