The first time Lisa Lampanelli roasted Donald Trump, it wasn’t even televised. The year was 2004 and the future “Queen of Mean” donned a full habit to play a woman who became a nun after sleeping with the man who was then still more than a decade away from getting elected president.
“Even funnier, in true Friar’s [Club] fashion, I was a Jewish nun who converted to Catholicism because he was so bad in bed,” Lampanelli recalls with a laugh on this week’s The Last Laugh podcast. Among her jokes that night was this one about his enormous ego: “Donald was so arrogant, he made me wear a mirror on my stomach so that when he went down on me he would have something to pleasure himself with.”
“Honestly, I am not going to sugarcoat it: I hate Trump with every fiber of my being,” Lampanelli, who recently retired from comedy to become a life coach, says now. “I roasted him twice and I was on The Celebrity Apprentice. I hate him for everything else other than those three things.” And despite his more recent inability to take a joke, she agrees with David Letterman that before he got into politics, Trump actually was a “good sport.”
“He has that Charlie Brown’s teacher kind of mentality where he doesn’t even hear the joke,” she explains. “He just hears ‘wah wah wah,’ Donald Trump, and laughs. He just likes the attention, so roasting him was literally a dream come true. And he wasn’t a president back then. He had talked about it, but I was like, ‘Well, that’s like the kid who says he wants a pony for Christmas.’ It's not going to happen.”
Seven years after the Friar’s Club event, Lampanelli delivered what ended up being her seventh and final Comedy Central roast performance at 2011’s Roast of Donald Trump. As has been well-documented, the one topic that was off-limits that night was anything that suggested Trump wasn’t the billionaire he claimed to be.
“It wasn’t just him,” Lampanelli says, confirming the story. “Every roast I’ve done—except for David Hasselhoff—had a rule, one subject or two that was off limits. So Pam Anderson, you couldn’t make fun of the hepatitis C thing, which I get. With Shatner, you couldn't joke about how they found his wife dead in a pool. With Trump, it was about the bankruptcies. But with Hasselhoff, by the way, nothing was off limits.”
Despite her brutal jokes that night—many of which directly referenced Melania, who was seated in the crowd (“If you were broke, you’d be fuckin’ me!”)—the future president liked Lampanelli so much that he asked her to be a contestant on The Celebrity Apprentice that following season.
“They also thought that because I was an insult comic, I would rough everybody up a little bit and I definitely ended up doing that,” she admits, calling her time on that reality show “literally the hardest thing” she’s ever done. “It was the most exhausting thing,” she says. “You had one day off a week, every other day was 20 hours. It was really horrible. If I did the show now I’d get kicked off the first week because I’m so boring.”
Lampanelli almost never interacted with Ivanka Trump during her time on the show, but says, “Don Jr. was my ally, because we all had like a mentor or whatever. He and I just liked each other. At the time he didn't seem as evil. It was afterwards that it started getting super creepy.”
After Trump got elected in 2016, Lampanelli says she “literally stopped watching the news.” Joe Biden’s inauguration was the first time she was able to put on CNN “without being scared” that it was going to be all about Trump. “He doesn’t come up that much anymore,” she says, thankfully. “Now it’s Cuomo. And he was so hot, what happened?! The Italians took a hit on that one.”
Now that Lampanelli has retired from comedy for good, she says there is one Trump joke she “regrets” she will never get to tell in public. With minimal goading, she shares it with me: “Remember he wanted to replace Obamacare with Trumpcare? Well Trumpcare is so bad for women, Caitlyn Jenner called her doctor and asked for her penis back.”
Next week on ‘The Last Laugh’ podcast: Stand-up comedian and author of the new memoir ‘Mixed Plate,’ Jo Koy.
