Hugh Hefner, Gilbert Gottfried and the Filthiest Joke Ever Told

Earmuffs, kids

By Kirk Miller

 
Gilbert
Share This

28 September 2017

RIP, Hugh Hefner.

We can argue about the man’s legacy — charming chauvinist, underrated civil rights activist, extraordinary publisher, cultural icon (in ways positive and negative). But for a man who was often the center of attention, his most notable moment in the 21st century arrived playing the part of a shocked spectator.

Behold, the cringeworthy glory of the New York Friars Roast of Hugh Hefner, taped shortly after the attacks of September 11th, 2001. Starring Jimmy Kimmel as host, Ice-T, Drew Carey, Cedric the Entertainer, Jeff Ross, Dick Gregory and Patty Hearst, among others, it can be remembered for a few things:

One, that inappropriate humor will win out over terrorism (it was OK to laugh again!). Sarah Silverman particularly slayed: “Let's all talk about the whore—the bunnies. No, bunnies aren't whores. They're paid monthly.”

And then, there was Gilbert Gottfried.

The comedian, who admitted he wanted to “be the first person to make a really-poor-taste joke about September 11,” started his act with “I have to leave early tonight, I have a flight to California. I can’t get a direct flight — they said I have to stop at the Empire State Building first.”

That didn’t go well.

His follow-up? It killed. Gottfried told his variation of The Aristocrats, the legendary anti-joke told in private amongst comedians.

The telling is absolutely epic. So epic, in fact, it spawned a great documentary. And though it never made the final broadcast (good luck finding the entire video portion online), here's the full audio for your NSFW enjoyment. 

As the greatest dirty joke ever told, Hef’s legacy wouldn't be complete without it.

Share This