Comedian Don Rickles speaks at the 40th AFI Life Achievement Award honoring Shirley MacLaine held at Sony Pictures Studios on June 7, 2012 in Culver City, California. The AFI Life Achievement Award tribute to Shirley MacLaine will premiere on TV Land on Saturday, June 24 at 9PM ET/PST. (Photo by Kevin Winter/Getty Images for AFI)

Legendary insult comic Don Rickles has had a long history of using irreverent racial humor in his routines. But at an American Film Institute tribute to Oscar winner Shirley MacLaine he may have gone to far. The 86-year-old quipped “I 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.” The crowd was uncomfortably silent. The Huffington Post reports:

Don Rickles told a racial joke Thursday night at the American Film Institute’s tribute to Shirley MacLaine that may have been more appropriate half a century ago at the Friar’s Club. This time, though, the object of Rickles’ mockery wasn’t Sammy Davis Jr. — but the first African-American President of the United States.

“I shouldn’t make fun of the blacks,” Rickles, 86, said according to The Hollywood Reporter. “President Obama is a personal friend of mine. He was over to the house yesterday, but the mop broke.”

Like many comedians of his generation, Rickles’ act has long included racial humor that would be considered unacceptable to today’s audiences. But as race relations evolved, it became rarer and rarer for comedians like Rickles to include such jokes in their act.

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