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Radio and TV host Don Imus, who died Friday at age 79, sparked his share of controversies, big and small, in a career that spanned nearly 50 years. His clash with the Clintons in 1996 ranks among the big ones.

Imus was the featured entertainment that year at the Radio and Television Correspondents Association dinner in Washington -- and the then-president and first lady Hillary Clinton were both seated nearby as Imus spoke.

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Though it was long before most people knew the name “Monica Lewinsky,” Clinton already had a reputation of being a womanizer – and Imus used a recent broadcast-booth appearance by Clinton at a Baltimore Orioles baseball game to make a joke at the president’s expense.

“The president was at Camden Yards doing play-by-play on the radio,” Imus told the audience, according to the Baltimore Sun. “Bobby Bonilla hit a double; we all heard the president in his obvious excitement holler, ‘Go, baby!’

“I bet that's not the first time he's said that.”

Most accounts say the Clintons did not appear to appreciate the comment.

At another point, Imus referred to the president as “a pot-smoking weasel.” While running for president in 1992, Clinton had famously admitted to smoking marijuana while he was a college student – but in a widely mocked statement he claimed he “didn’t inhale” and “didn’t try it again.”

Other Imus jabs targeted Hillary Clinton’s legal troubles at the time, Newt Gingrich’s lesbian half-sister, and then Sen. Joe Biden’s hair transplant, The New York Times reported.

Imus’s performance was considered so shocking that the correspondents association wrote a letter of apology to the Clintons, according to the Times.

Don Imus, left, was never invited back to a Washington dinner after speaking with President Bill Clinton and first lady Hillary Clinton in attendance in 1996.

Don Imus, left, was never invited back to a Washington dinner after speaking with President Bill Clinton and first lady Hillary Clinton in attendance in 1996.

Kenan Block, then the outgoing president of the group, told the newspaper that Imus had assured him he wouldn’t insult the Clintons.

“He said, “I can’t tell womanizing jokes about the president with his wife sitting right there,’ and ‘Don’t worry, I’m not going to embarrass myself,’” said Block, who was a producer for “The NewsHour with Jim Lehrer” on PBS.

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Many years later, in 2014, Politico published a mock rejection letter, purportedly written in 1999 by Clinton aide Mark Katz, in which Clinton declines an invitation to be a guest on Imus’s show.

“Just so there is no confusion,” the letter says in part, “allow me to parse ‘no’ for you.

“Hell no.
“Notta chance.
“Negative.
“Nyet.
“N. O.
“O-Nay.
“That’s a big 10-No, good buddy.
“Take a regular “no” and supersize it.
“Right after I go on Rush Limbaugh.”