When Jay Leno was in his heyday as the host of The Tonight Show, he had quite a cult following, as millions of Americans tuned in every night to catch his show. Despite this incredible connection with the fans, Leno is all the same famous for feuding with other celebrities.

Superstar radio host Howard Stern is openly hostile towards Leno, accusing him of stealing material from his show, as well as other programs. The former late night show host also infamously fell out with Conan O'Brien. This was after making Conan believe that he would relinquish the show to him, only to then go back on his words.

Leno has also had a knack for getting himself in hot water in the past, like when a racist comment he made on America's Got Talent sparked a massive backlash against him. It is perhaps no surprise, then, that fans seem to have little to no sympathy for the comedian for one time when he was thoroughly roasted by the legendary 'Merchant of Venom,' Don Rickles.

What Happened Between Don Rickles And Jay Leno?

Leno was in hot water with his guest from the very beginning, having kept him waiting for one and a half hours backstage. “My god. You had me waiting for an hour and a half backstage looking through your funny carpets,” Rickles went off sarcastically.

Rickles then went for Leno’s performance in the time when he was apparently held up behind the scenes. “It was wonderful watching you crash into a fence,” the legendary comedian quipped. “What funny stuff really. Like an hour and a half of watching a blind guy go into traffic or some damn thing.”

Leno could barely get a word in, as his guest kept his leg firmly on his neck. “You invite guests and you stand out here for an hour and a half with your cockamamie trick-or-treat little stories and gimmicks and it’s not going over, forget about it!” Rickles went on.

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The dyslexic TV host maintained an uncomfortable composure all through, but he managed to somewhat turn the tables around, when he retaliated with why he had to keep his guest waiting that long.

Jay Leno Is No Stranger To Dark Humor And Roasts

“Normally when we have a big star, we bring them right out,” Leno teased. “Well and sometimes you have to fill.” This sent the audience into a fit of laughter, but Rickles did not look impressed at all. “I don’t see the humor in that,” he retorted.

Leno is no stranger to being on the end of dark humor and roasts, but it doesn’t always go down as well as it appeared to with Rickles. He did not, for instance, take it well when fellow comedian Louis C.K. made a teasing comment about his face.

“I hope I can say this without insulting you. You're the weirdest-looking person on the planet earth. There is nobody that looks like you,” the bald-headed C.K. had jabbed, to which Leno responded: “It’s because I have a head full of hair.”

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It was a different case altogether when it came to taking it from Rickles, perhaps understandable given the stature his guest enjoyed in the world of comedy. The California-born comic had been in the business since 1955, and was well known for his role in the NBC sitcom from the ‘70s, C.P.O. Sharkey.

Don Rickles Did Not Spare The Audience Either

The ten-minute interview was pretty fast-paced, with a lot of off-the-cuff moments - most of which came from the esteemed guest. When at one point Leno pointed out that Rickles was Jewish, the comedian picked out an African-American man on his host’s band.

“What’s that gotta do with it?” he asked. “What is this, a Nazi movie? What’s Jewish gotta do with it?... He’s black, did I make a big thing out of it?” He then stood up and feigned to walk off set. “Okay, that means I gotta go work the border,” he said, in a joke that perhaps might not go over too well in modern times.

Even the audience was not spared from the endless roasting that Rickles had to dish out that night. “Have you ever been to China, miss?,” he asked a woman in the crowd, as he recalled a past trip he took to the country himself. “You ever been outta your house?”

‘He managed to roast every race, 2 sports teams, 3 countries, 5 celebrities, 7 audience members and Leno like a thousand times in the span of 10 minutes,’ one fan observed in the YouTube comment section, as Rickles’ unique gift continues to be recognized nearly five years since he died in 2017.

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