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Gilbert Gottfried Always Knew Where the Line Was. Here Are Three Times He Went Over It.

Gottfried's most shocking jokes weren't necessarily mean, but they were told to the wrong audience at the wrong time

Gilbert Gottfried over the line watch worst most offensive jokes
Gilbert Gottfried, photo by Brad Barket/Getty Images
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    Among the big comedy stars of the modern era, nobody enjoyed offending their audience more than Gilbert Gottfried. “You want to feel like you’re going to go on a ride and there’s a chance it will kill you,” he said in 2019.

    Gasps and boos were a common soundtrack to his sets, and his roasts became legendary for their shocking rudeness. He told a filthy joke about Joan Rivers and handjobs, unfavorably compared Roseanne Barr to livestock, and said that “Donald Trump has done so much damage to the New York skyline, instead of calling him The Donald, they should call him the 20th hijacker.”

    Gottfried passed away on April 12th, and tributes have come pouring in, with fans and fellow comedians recalling all the times he tiptoed right up to the line without going over it. But that’s not his whole story. As he liked to say, “I think twice but do it anyway.” And while his humor would often, in his words, “clear the audience out,” more than once that attitude got him in real trouble.

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    Being offensive isn’t a virtue, and we’re not here to celebrate his meanest jokes. In fact, all of the comedy bits collected below would likely have gone without remark if they had been performed in front of different audiences at a different time. That indifference to decorum is part of what made Gottfried special. Love it or hate it, his act required real bravery. Night after night, he performed the comedic equivalent of a high wire act without a safety net. Here are three times he fell.

    Gottfried Gives Paul Reubens a Hand at the 1991 Emmy Awards

    In July of 1991, Paul Reubens, known to many as Pee-Wee Herman, was arrested for masturbating at an adult movie theater. One month later, Gottfried presented the Emmy Award for Outstanding Writing in a Variety or Music Program. And he did eventually do just that. But he opened with approximately 90 seconds of masturbation jokes.

    “Masturbation’s a crime, I should be on Death Row,” he told the live national audience. “To think that at age 14, I was already Al Capone.” Fox managed to censor his monologue for the tape-delayed west coast broadcast, and the experience reportedly left him temporarily blacklisted in Hollywood. But the ill-effects didn’t last very long, and Gottfried was once again back in Hollywood’s good graces after his scene-stealing turn as the parrot Iago in 1992’s Aladdin. Easy come, easy go, easy come again.

    “Too Soon!”

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    Gottfried is sometimes credited with telling the very first public 9/11 joke. At the Friar’s Club Roast of Hugh Hefner — an event that raised over $500,000 for victims impacted by the September 11th terrorist attack — Gottfried opened by complaining that he couldn’t get a direct flight because “they said they have to stop at the Empire State Building first.”

    As he later recalled, “They were booing, hissing, chairs screeching back… You could hear people getting really angry, shocked, and gasping.” Nearly everyone who was there that night remembered one man repeatedly yelling, “Too soon!”

    Gottfried recovered, in a way. “I go into The Aristocrats because I figured, “Why not go into a lower level of hell? I’ve already lost them beyond belief. Fuck it.” He then launched into a graphically obscene take on the popular joke format involving a family in a talent agent’s office. It’s a famous moment, captured in the film The Aristocrats, and best of all, the other comedians in the room knew what exactly what he was doing. Fellow roaster Rob Schneider was laughing so hard he fell out of his chair. Afterwards, “Too soon,” became something like Gottfried’s rallying cry, to the point where Funny or Die put him in a “Too Soon” video where he joked about tragedies throughout history.

    Waves of Regret

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    On March 11th, 2011, a massive undersea earthquake caused a tidal wave to sweep over Japan, killing nearly 20,000 people. Shortly afterwards, Gottfried logged on to Twitter.

    “Japan is really advanced,” he wrote. “They don’t go to the beach. The beach comes to them.” As outrage grew, Gottfried doubled down on mocking the tragedy. “Japan called me. They said ‘maybe those jokes are a hit in the US, but over here, they’re all sinking.'”

    Those tweets probably cost him more money than all of his other tasteless jokes combined. On March 14th, Aflac announced that they were firing Gottfried as the voice of their duck mascot — a role he had held since 2001.

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    Gottfried remained uncowed, and he continued to use his Twitter account to post edgy jokes right up until the end. His last tweet before his death mocked Will Smith slapping Chris Rock at the Oscars. “Which is the worst crime? Chris Rock being physically assaulted or Chris Rock telling a joke?” he wrote. With it, he included a photo of himself next to Rock. It was a rare moment of sappiness from Gottfried, showing that the burn was meant with love.

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