The Cardinal Sins of Comedic Tweeting

Lizz Winstead reacts to the news the hashtag #grouponrejections was No. 5 in the world. Just minutes later, it plateaued at No. 2.

Image: Michael del Castillo

Three heavy-hitting Twitterati sat side by side on a stage Wednesday and invented a hashtag—#RejectedGroupons. Forty minutes later it was ranked the second-highest hashtag in the world, with star tweeters like Will Ferrell joining in the fun.

Such is the power of comedic tweeting.

Jon Friedman (74,029 Twitter followers@friedmanjon), creator of the award-winning The Rejection Show and former Late Night With Jimmy Fallon blogger; Lizz Winstead (38,405 Twitter followers @lizzwinstead), co-creator of the Daily Show; and writer Julieanne Smolinsky (55,891 Twitter followers @boobsradley) joined forces this afternoon to give an audience of about 100 people a lesson in comedic tweeting.

Since senses of humor vary dramatically, we thought it would be interesting to share not what you should do, but what Winstead called the Cardinal Sins When Trying to Be Funny.

Lizz’s advice: If it’s the first thing you thought of, trust me, someone else already thought of it. I say always go with the second thing you thought of. So check, and if someone else already wrote it, don’t write it. Like, “John Boehner’s orange.” I know.

Jon’s advice: Don’t overthink it, I think, is a main ingredient for being funny. If you thought it was funny, tweet it out there, and you show people what you think is funny. And don’t try too hard to imitate someone else’s voice that you admire. It’s like, “Steve Martin would have said it this way, so let me try to alter it into his voice.” Just use your own voice.

Julieanne’s advice: Too much sexy stuff and too much current stuff. I think if you’re making the same joke that everybody made about Whitney Houston, like, 10 minutes ago…well, that’s just a poor example, that’s just in poor taste. Be careful of making the same joke that everyone else is making.

In the end, it is your Twitter feed and your voice.

“That’s the beauty of it,” said Friedman. “You can do whatever you want. Trial and error. Try a balancing act. Do more funny things, do more political things—change it up the next day. It’s your own. If you start worrying too much about what you’re doing, that’s when you’re going to start thinking too much and have a block.

And Winstead agreed.

“There’s no formula,” she said. “Just be authentic because people can see through bull---- even in 140 characters.”