Donald Trump is no stranger to roasts. In 2011, he was lampooned by Snoop Dogg on Comedy Central. And it was his skewering by Barack Obama later that same year at the White House Correspondents' Dinner that allegedly fueled his presidential ambitions. But it arguably all began in 2004, when Trump was guest of honor at the Friars Club's annual roast.
At the show emceed by Regis Philbin at the height of The Apprentice's popularity, Trump laughed heartily at the parade of bad-hair jokes and cracks about beauty pageants. ("He's the only guy who could sleep with 72 virgins without having to blow something up," quipped insult comedian Jeffrey Ross.) Occasionally the cuts went deeper, with Richard Belzer calling Trump "the man, the legend, the f - ing grifter wrapped in a fraud perpetrated on society." Robert Klein needled Trump for loving the TV limelight - to the exclusion of everything else. "He doesn't give a shit about any of the other stuff," observed the comic, "which involves people losing everything and going on the street with pencils in Atlantic City begging."
When it came time for his turn at the dais before a packed ballroom at the New York Hilton, Trump began by apologizing to then-fiancee Melania, who appeared shell-shocked after enduring a barrage of zingers. (Curb Your Enthusiasm's Susie Essman had joked, "Your casinos are going down, Donald. In fact, the only thing you own that's not going down is Melania.") Said Trump, "I didn't have the courage to tell Melania she was going to be called some of the things she was called today. And darling, you're a wonderful woman. Thank you for putting up."
The comment drew a warm round of applause. Moments later, Trump turned to Katie Couric, who sat alongside then-NBC boss Jeff Zucker at the table of honor. "The first word she heard [at the roast] was 'c - ,' " said Trump. "And then it only got worse."
This story first appeared in the April 13 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.