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Three years ago this summer, Ann Coulter tried to be funny. It didn’t go well.
“Was she there?” Jeff Ross jokes when I bring up Coulter’s infamous performance at the Comedy Central Roast of Rob Lowe. “I barely remember her being there.”
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On this week’s episode of The Last Laugh podcast, Ross—who earned the nickname Roastmaster General by roasting everyone from Pamela Anderson in 2005 all the way up through this summer’s roast of Alec Baldwin—admits that it was his idea to book Coulter in the first place.
He was looking for a political figure to make the event more “relevant” just a few months before the 2016 election and Coulter was promoting her book In Trump We Trust (actual subtitle: “E Pluribus Awesome!”). “I like having big targets there,” Ross says. “How many Rob Lowe jokes can I make? I want to make some Ann Coulter jokes!”
“I had not fully taken her seriously as a pundit,” he adds, explaining that he used to run into her socially at the Comedy Cellar in New York. “To me, she seemed like a comedian. She was friends with comedians, she would say outrageous things. We try to get a laugh, she was trying to get a jaw-drop.” He always assumed she was “exaggerating her opinions” for shock value, much in the same way comedians might embellish a story for comic effect.
According to Ross, the writers working on the roast wrote her an “amazing, self-aware speech, that if she had delivered, she would have made a lot of new fans.” But she didn’t like it. “And she brought in a couple of friends from Fox News to help her write her speech, which she started by taking out her new book and putting it on the podium,” he says. “Now, if there’s ever a way to get the fans to hate you at a roast, it’s to start talking about yourself, and your book.”
Coulter was getting “destroyed all night” by the professional comedians on stage, Ross says, including British stand-up Jimmy Carr, who said, “Ann is one of the most repugnant, hateful, hatchet-face bitches alive,” adding, “It’s not too late to change, Ann. You could kill yourself!” Nikki Glaser told Coulter, “The only person you will ever make happy is the Mexican who digs your grave” and Saturday Night Live star Pete Davidson straight-up called her a “racist cunt.”
“Even she built up goodwill by taking the jokes all night,” Ross says. “You could see she didn’t like it in her face, but she didn’t really snap back. She took it. So now she goes up near the end and people are kind of rooting for her to see what she says. They want to be entertained. It doesn’t mean you have to agree with her policies to say, ‘That was a good line.’”
But when Coulter finally took the stage, she drew boos for plugging her book and groans for lame jokes about Hillary Clinton. After they taped the roast but before it came out, Coulter claimed that she didn’t really know what she was getting into and accused Comedy Central of editing it to make her look worse.
“She said that before the show even aired,” Ross marvels. “So what we did was, we queued up her unedited, raw appearance and basically let her know that if she kept saying we were messing with her, we were going to release it. We made her look better than it was.”
Even Comedy Central president Kent Alterman told me at the time that Coulter was not “singled out,” joking, “We didn’t prevent her from watching any roasts.”
Ross maintains that she would have been a lot better off delivering the more “self-effacing” jokes the writers wrote for her. But instead, “she blew it.”
“I still like her, because she came to the roast,” Ross, who says Coulter snubbed him at a party recently, adds. “I don’t agree with anything that she says on social media or in the media in general, but I also understand that we’re all human beings and she was willing to put herself out there and show up. I have to show some grace. And she didn’t take it well.”
Next week on The Last Laugh podcast: Writer and star of Late Night, Mindy Kaling.
