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Duane Hoffmann / msnbc.com
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msnbc.com contributor
updated 9/9/2008 3:25:38 PM ET 2008-09-09T19:25:38

At a Friars Club roast of Hugh Hefner three weeks after the Sept. 11 terrorist attacks, comedian Gilbert Gottfried not only pushed the envelope, he set it on fire. He was at the podium, about to launch into the abundantly filthy “Aristocrats” joke that inspired an entire documentary film, when he mentioned that he had tried to get a direct flight “but they said they have to stop at the Empire State Building first.”

If it’s possible to hear a cringe, this was the time. One man yelled out, “Too soon!” and a few gasps and groans were also audible. The walls of the Friars Club have heard a lot of tasteless remarks over the years from some of comedy’s foulest mouths, but this was in an historic class by itself. Fortunately, perhaps owing to Gottfried’s standing among his peers and serving as a tribute to his own adroitness, he managed to squirm out of the predicament by quickly launching into arguably the most disgusting version of the “Aristocrats” joke ever presented in mixed company.

That probably was too soon to crack wise about the most tragic and traumatic event in American history. But who’s to say? With the anniversary of 9/11 on Thursday, the old show biz adage reminds us that “Comedy is tragedy plus time,” but it neglects to mention just how much time is necessary.

“The pain is still raw for many people and for our country,” noted Mark Katz, a speechwriter and humorist who runs the Sound Bite Institute. He specializes in crafting jokes for VIPs in the political and corporate arenas. “But if you have a point that is salient to 9/11, there could be a funny way to get at it.

“The audience will let you know. The ‘Ooooh’ is the umpire’s call of the audience.”

Andy Kindler is accustomed to that call. He’s been doing standup for years and lately has served as a regular correspondent on “Late Night With David Letterman” and can also be seen on Comedy Central’s “Lewis Black’s Root of All Evil.”

“There are no rules in comedy, but certain things are a matter of taste,” he said. “Joe Biden said Rudy Giuliani only says three things in a sentence: a noun, a verb and 9/11. I thought that was great.”

Breaking the ice after Kennedy assassination
While Gottfried’s 9/11 joke came three weeks after the Twin Towers came down, Kindler pointed out an even riskier bit by one of the edgiest comics ever. Shortly after President John F. Kennedy was assassinated, Lenny Bruce told a nightclub audience, “Vaughn Meader is screwed!” a reference to a then-popular impersonator whose entire career was based on doing Kennedy. There is also an alternate story — perhaps apocryphal, perhaps not — in which Bruce said there were two graves that had just been dug at Arlington National Cemetery, one for Kennedy and one for Vaughn Meader.

“That’s the way Lenny Bruce broke the ice and it worked,” he said of the first example. “You can absolutely use 9/11 as a reference point to something else.”

A gag about planes crashing and people dying is a gag not worth telling in just about any situation. But a related topic could be hilarious.

“I think the only jokes that came out of 9/11 were more about airport security,” said Robert Koch, a standup comedian based in Los Angeles who has worked the club circuit and also warms up live audiences before sitcom tapings. “The airport security and the shakedown. The hell of travel now after that. That was the only real safe area of comedy on that subject, that and Bin Laden jokes. The search for him and the cave he’s in.”

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The problem for every comic and any joke is that it’s O.K. to be offensive, just not too offensive. It is yet another judgment call. And chances are, there is somebody out there who will be offended no matter what.

“I do a joke about getting into a fight with a guy in a wheelchair,” said Jackie Flynn, a comedian who has done the clubs and the Las Vegas stages for years and now works a lot of corporate events. “I didn’t really get into a fight with a guy in a wheelchair. It’s a joke. People in wheelchairs laugh. The only person who ever complained was somebody who knew somebody who was in a wheelchair. There’s always somebody taking up the cause of somebody else.”

“For me,” Flynn added, “you have to push the envelope. By the same token, you have to be careful about at whose expense you’re making a joke about. But if you’re pleasing everybody then you’re doing something wrong, too.”

One of Kindler’s most famous lines was a salvo directed at fellow comic Dane Cook, a polarizing figure in the business, and his staggering rise to prominence, likening it to that of Adolf Hitler. “The only difference,” Kindler cracked, “is that Hitler had a point of view.”

“Some comics just say things for shock value,” he said. “Then others push the envelope because they’re funny. It’s about the point of view of the comic.”

Quite often a joke isn’t just a joke. Katz said there is often more than meets the ear.

“The most famous example on a high-profile stage is George Bush’s WMD joke at the (2004) Radio and Television Correspondents’ Association dinner,” he said. A video shows the President poking around his office, looking for weapons of mass destruction.

“Again, what was the joke about? What truth or subtextual thought was there for that joke. It was designed to be a self-deprecating joke, except the punchline was at the expense of the American people.”

When it comes to jokes about 9/11, there is still no rulebook. Perhaps comedy from any subject, including tragic events in history, comes about simply because people are in dire need of a good laugh.

Koch remembers he was working at a sitcom at the time of the attacks. “The world was in shock. When we did the first taping, we just told people, ‘Through all that’s happened, we appreciate you taking the time. It’s O.K. to let yourself laugh.’ They wanted something. They needed something. The air was heavy. Nobody wanted to dishonor the seriousness of what happened.

“They needed permission to laugh.”

Yet seven years later, the subject matter is still dicey. It’s all right to make jokes about Abe Lincoln and Pearl Harbor, because a lot of time has gone by. But make the wrong 9/11 joke and you may live to regret it.

“The reasons why politicians and public people are so cautious,” Katz explained, “is that the right joke will be reprinted in Newsweek, and the wrong joke will be reprinted in your obituary one day.”

Michael Ventre is a frequent contributor to Msnbc.com. He lives in Los Angeles.

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