Jeff Ross, Roastmaster General

Photo: The Howard Stern Show

Jeff Ross stopped by to promote his new Comedy Central series, ‘The Burn’, but Howard was more interested in Jeff’s legendary roasting skills: “Is it hard to say something really shitty about someone to their face?” Jeff said that was exactly the point: “I would only say it to their face. [Otherwise] it’s hypocritical. A true roastmaster says it right to ’em.”

For example, Jeff remembered a joke he’d made about Penny Marshall: “I learned a lesson on that one, Howard, because, like you said, it was behind her back.” At the Friar’s Club roast of Rob Reiner, Jeff had joked: “How do you even embarrass a guy who married Penny Marshall? What was your wedding song? ‘How Much is that Doggy in the Window’?” Later, when he was hired to roast the Maloof Brothers, Penny was in the audience, heckling Jeff from Vince Neil’s lap: “Then she started coming toward the podium, and I said, ‘Whoa whoa whoa–which one were you? Lenny or Squiggy?'” Penny immediately backed down, humiliated, but Jeff found himself disinvited from the Maloofs’ afterparty.

A Brief, Impromptu Roast

Asked to roast the crew, Jeff shot off some impromptu one-liners: “Robin’s not here today. There’s no one here to fake-laugh at my jokes and step on the punchlines. There’s no minorities in the studio! The closest thing you have to a person of color are the brown stains on Tim’s fingers.” Jeff also zeroed in on Howard: “The only people who want to f’ Howard are those Sirius executives.”