Jeff Ross says Milton Berle tried to trip him up at first roast

Roastmaster General Jeff Ross remembers a close encounter with late comedy legend Milton Berle, who wasn’t all that supportive of his colleague.

As Ross recalled it on Wednesday’s episode of The Howard Stern Show, when he first worked with Berle, who died in March 2002, on a roast, the kind of comedy which Ross would go on to become known for, Berle wasn’t a fan.

“Milton had giant hands and every time I got a laugh from behind the podium, Howard, he would poke me in the ribs, and I would jump,” Ross said. “And then I keep going, and I’m hitting, pretty consistently getting good laughs and, finally, he’s just interrupting me. I’m killing, and he’s interrupting me.”

Ross took it as long as he could.

“Finally I go ‘Milton, didn’t I see you in an antique shop this morning [for] 800 bucks?'” Ross said. “And Milton gets up and starts doing a two man show, and I’m trying to keep up with him. Then, you know, there were all these celebrities, like airplane wings, down the dais.”

It was The Music Man star Buddy Hackett, who died in 2003, that came to Ross’ defense.

“Buddy Hackett just bellows, ‘Hey Milton, let the kid work. Remember when you used to,'” Ross said. “Milton runs down, kisses Buddy Hackett on the lips. The place explodes. And I go, ‘Oh, there it is, Milton and Buddy, over 80 years of homosexual experience.’ And the place just goes wild, and I felt like I’d found my Yankee Stadium in that moment.”

Ross was mystified as to why Berle would act as he did.

“I went back to the Friars Club afterwards, and I said to Buddy Hackett ‘Why would Milton do that?'” Ross recalled. “He goes ‘He doesn’t like when other people get a lot of laughs. He was trying to trip you up.'”

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Ross decided to ask the former talk show host himself.

“I went and had a cigar with him and I said, ‘Milton, why would you poke me like that?'” Ross recalled. “He just said, ‘Remember, they only remember the homeruns. It means I had too many jokes and just edit down to the home runs. And even though he was trying to interrupt me and f— me up a little bit, I was like, ‘That’s really good advice.’ And Milton and I did go on to become very good friends. I think he was testing me.”