Jay Leno Defied Military Orders and Roasted Ronald Reagan

Believe it or not, there was a time when Jay Leno was a young, up-and-coming comic. Elder Statesman Jay probably has earned a decent amount of respect from military brass, but the younger version with the wide tie who occasionally filled in for Johnny Carson? We’re guessing not so much. So when a general confronted Leno prior to an early 1980s appearance at a White House Correspondents’ Dinner, we’re guessing the military man scared the crap out of the comic.

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It was Leno’s first go-round at one of these events and his assignment was to give Ronald Reagan a hard time, he told Kelly Clarkson. But the general, bedazzled with combat medals, had other ideas. “That's the President of the United States, you understand? That is my commander-in-chief,” the general barked, poking his chest for emphasis. “You do not denigrate him. You do not make fun of him. He is the President of the United States. He is my commander. DO YOU UNDERSTAND?” 

A terrified Leno managed a “yes, sir” despite the fact that denigrating and making fun of the President was exactly what he had been flown to Washington to do. “Oh man, I’ve got to change my act here,” thought Leno. 

Two minutes later, Leno was approached again, this time by Secretary of State George Schultz, cocktail in hand and already three sheets to the wind. “Leno, come here, come here,” Schultz said. “You get out there and you nail Ronnie's ass to the wall!”

Leno started to protest. “But that general…”

“Screw him,” slurred Schultz, “he works for me! And I'm telling you what to do. You make fun of that black thing on Reagan's head, you understand?” (We’re guessing “that black thing on Reagan’s head” referred to the stiff head of hair that always looked like it had been dyed with black shoe polish.)

“I didn’t know what to do now,” Leno confessed to Clarkson.

“What did you do?” she asked.

“Oh, I nailed him to the wall.”

How mean was Leno? His opening joke was directed at Reagan’s wife Nancy, who had recently received a humanitarian award. Leno hit her with “I’m glad you beat out that conniving Mother Teresa.” The President laughed — hey, the poke was at Nancy’s expense, not his — and Leno knew that as long as Ronnie was chuckling, the general couldn’t say a damn thing.