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The ‘forgotten’ Trump roast: Relive his brutal 2004 thrashing at the New York Friars Club

Comedian Michelle Wolf will have the odd task of roasting an empty chair in President Trump's absence. (Video: Nicki DeMarco/The Washington Post)
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When the White House correspondents’ dinner is at its most entertaining, it’s a good roast, where the ribbing is done in good fun. No one should be spared — the media, members of Congress, random celebrities in attendance and, least of all, the president of the United States, who gets to roast right back.

And although President Trump won’t be in the room Saturday to endure jokes cracked at his expense, breaking with a 36-year tradition, he attended a much more brutal roast, enduring comedic insults of the highest caliber. Long before he became a polarizing politician and president, Trump was a New York institution who participated in one of the most New York of rituals: a Friars Club roast.

Reviewing old YouTube clips and reports of Trump’s February 2004 roast today is like stepping into a bizarro-world, where the vicious insults lobbed at “The Donald” were nothing less than cracking wise at the expense of a New York businessman and reality-TV star.

The Friars Club roasts always attracted a random assortment of old-timers, TV stars, athletes, New York icons and a roster of insult comics. It was considered an honor to have all those in the room tear you to pieces, and it usually ended with kind words.

“We always say this at the end of a roast, and we mean it so sincerely today, we only roast the ones we love,” Freddie Roman, dean of the Friars, said when introducing Trump at the conclusion of the event.

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Though Trump participated in a more heavily produced Comedy Central celebrity roast seven years later, the Friars Club one was its grittier, untelevised precursor. Regis Philbin served as host. Also in attendance: Mike Wallace; Rev. Al Sharpton; Stone Phillips; Abe Vigoda; boxer Michael Spinks; Victoria Gotti (from reality TV/the mafia); Katie Couric; and Jeff Zucker, then head of NBC and currently the president of CNN — which, in 2017, Trump labels as “fake news.”

But in 2004, Trump paid tribute to Zucker as “truly great and the brilliant man behind NBC.” At the end of the roast, Trump said, “NBC, if you look at what they’ve done over the last four or five years — believe me, everybody wanted ‘The Apprentice,’ but he wanted it more and he knew it was going to work, and it did work, big league, and this is truly a great guy.”

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The New York Times was on hand for the event, reporting that “Trump smiled and laughed along yesterday afternoon as he sat for two and a half hours in a ballroom of the New York Hilton, while a series of comics, celebrities and so-called friends absolutely savaged everything from his brushes with bankruptcy (his casinos have seen better days) to his fiancee (Melania Knauss, who is young, pretty and accented) to, yes, his infamous comb-over (just plain bizarre).”

Zucker had his own cracks about Trump, per the Times: “Donald, I got the invitation for the wedding, but I can’t make it. I’ll catch the next one.” He then added that the wedding would be a great affair, with a cigar room for Trump’s friends and “for Melania and her friends, a bouncy castle.”

When Sharpton stepped to the microphone, he said he’d asked about the diversity in the roast crowd before agreeing to participate. “They said, ‘That won’t be a problem, we’ll have has many blacks in the crowd as Donald has living in his buildings.’ ” He then added: “The truth is Donald asked me to perform one of his weddings. We fell out when he wanted me rather than read the vows, to read the prenuptials.”

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Aside from the random celebrities were the professionals comedians who were regular presences at these roasts. They said a bunch of really vulgar stuff, including comedian Jeffrey Ross, who is now a regular presence at the Comedy Central events and is considered “Roast Master General.”

“He’s the only guy who could sleep with 72 virgins without having to blow something up,” Ross said as Trump smiled beside him. “Everything he puts his name on loses money. The Trump sign is like a 50-percent-off tag.” (Ross offered a few kind words at the end of his set, including: “I think you should be running for president and those other two guys should be hosting reality shows.”)

“The reason Trump puts his name on all his buildings is so that the banks know which ones to take back,” comedian Rich Vos said, according to the Times.

Lisa Lampanelli, dressed as a nun, played a character: Trump’s ex-girlfriend. “He seems very happy,” she said, “with his beautiful fiancee, Insert Name Here.”

“You know what she sees in you?” comic Susie Essman said to Trump. “A billion dollars and high cholesterol.” (According to the Times, “That was, for the record, the only joke the salty Ms. Essman told that could possibly be published in a family newspaper.”)

Richard Belzer referred to Trump as “the grifter wrapped in a fraud perpetuated on society.”

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According to the Hollywood Reporter, Robert Klein highlighted Trump’s love of attention and the limelight: “He doesn’t give a s— about any of the other stuff — which involves people losing everything and going on the street with pencils in Atlantic City begging.”

After the roasters finished, it was Trump’s turn to take the mic. He didn’t have many jokes — he made a crack about Hugh Hefner and dumb blondes, and some odd anecdote about Katie Couric hearing the c-word during the event. But he didn’t have big comebacks to vanquish all those who had taken their turns trying to embarrass him into laughter.

About all the Atlantic City jabs, Trump just had this to say: “It’s doing very well, just watch. You watch.”

And we see, even then, Trump’s habit of emphasizing crowd sizes — one he carried with him to the White House. Just before wrapping up the 2004 event, Trump said he had resisted participating in the Friars Club tradition. But the club dean had convinced him.

“He said this is the 100th year of the Friars Club,” Trump said, “and he just told me it’s the biggest crowd they’ve ever had.”