Tweet and learn: Comedians share what it takes to be funny in 140 characters

As someone who spends an inordinate (read: disgusting) amount of time online and using social networks, one of the questions people most often asked me is, “What’s the point of Twitter?”

There’s something about the utility,  the speed, and the relevance of Twitter that seems to evade general Internet users. As a social network, a photo-sharing service, and an advertising mechanism – among other things – its true purpose can get muddled in the all the roles it serves.

But there is one thing Twitter definitely does, and that’s acting as a soapbox for anyone who wants to get up and take advantage of the spotlight. And surprise – among the willing participants are comedians.

At a recent keynote for Social Media Week in New York City, a number of notable comedians took the stage to dissect just how to get a laugh in 140 characters. Generally, if you have to ask how to be funny, you should probably just give up now – but some of the best minds and mouths behind Twitter comedy had some wit and wisdom to share with us all. During the panel, the audience even had a chance to test their skills in real time to get #rejectedcitizenshipquestions to top trending status.

(Spoiler alert: We totally did it, and yours truly landed among the top tweets a few times. Just saying.)

How far is too far?

Twitter has more than 500 million users, so odds are if you plan to push the envelope, you’re going to offend someone … maybe everyone. Lizz Winstead, (@lizzwinstead) co-creator and former head writer of The Daily Show, often tweets about political moments and thus knows this all too well. “I tweet to the outrage of the moment, and if there’s humor in it, I’ll find it,” she says.

XOJane and GQ writer Julieanne Smolinski (@boobsradley) also points out that when taking risks, you likely care more about what you said than any of your followers. “Once I was getting on the subway and sent a tweet, and then sat there in anxiety because I couldn’t get back online to delete it,” she says. “But when I got service and logged on, like one person had cared.”

Bottom line: Haters gonna hate. “I use Twitter personally to speak truth through humor, and if I’m not pissing people off, then they’re not listening,” says Winstead.

While Winstead says to never apologize, stand up comic and My Damn Channel’s Jon Friedman (@friedmanjon) admits a recent incident led to his deleting a tweet and issuing an apology. “It was Ash Wednesday and I joked about how not washing that ash off last year was worth it,” he says – and the offended Catholics came calling. “I mean, my last name’s Friedman, I’m obviously Jewish. So I took it down and felt a little bad about that.”

Building your voice and finding the followers

Starting a Twitter account and staring at the words “0 followers” is depressing and intimidating at the same time. What’s the point of typing out a tweet and sending it into the ether, where literally no one will see it? It’s these first steps that are the hardest, and Winstead says you should play by Twitter’s rules to get started. Use trending hashtags, take part in games around promoted tags or accounts.

Friedman says you can’t care too much about your audience – basically, don’t pander. “Thinking about what other people might think is funny will always screw you up,” he says.

Timely parody accounts: Yay or nay?

The day the BronxZooCobra slithered his way onto the Internet was an iconic one. It was the appearance of one of the first parody accounts, with some genius tweeting the elusive cobra’s activity as all of New York searched for him. But now, thanks to us Internet-obsessed denizens, the whole momentary parody account thing has been played out. It’s been played out hard.

“I think Jake Fogelnest meta’ed that out of existence,” says Smolinski, referring to the ingenious user who grabbed the Russian meteorite handle and did nothing with it other than to tell everyone to just stop it already. This is why we can’t have nice things.

Still, Winstead says she has a secret account to use as a writing exercise. “No one knows that I use it or that it’s mine, but I use it as a creative writing tool.”

Lesson to be learned: If you really want that 15 minutes of Twitter fame, go ahead with the scheme – just know you’ll attract plenty of haters and little or no long-term relevance.

Curbing your Twitter enthusiasm

Once you get a taste for the Twitter, it can be difficult to ration yourself.

“For me it’s like office hours,” says Winstead. “I have a whole system for how I use Twitter; I feel like it’s work.”

As far as other social networks, all three say Instagram is their next stop, although for more personal use. They’re all interested in experimenting with Vine (As has actor and filmmaker Adam Goldberg; if you haven’t peeked at his Vine, you must. Now.), and still admit Facebook is a must-have.

LinkedIn? Cue the crickets. “Get off LinkedIn!” says Smolinski. “I call it ‘TheMissingLinkedIn,'” echoes Winstead. “What happens there? I don’t know… there’s nothing fun there, right?”

Weird science

While the rest of the world – most notably, the PR population – is hell bent on getting analytics and metrics from their Twitter accounts, the panel members don’t take much stock in the data.

“It’ll make me crazy,” says Friedman. “And checking that gets in the way of being funny. Who unfollowed you, how much [a number] dipped, it gets in the way of what you’re doing.”

“There’s an app that tells you if anyone’s stolen your jokes, and I have a comic friend who’s obsessed with that and the app that tells you when someone unfollows you – he looks at that stuff religiously,” says Smolinski. “I won’t let myself look [at that stuff] because it’s not worth it.”

Winstead remarks that Twitter’s constant cleaning of house for the many, many spam accounts on the site also affects this number, and can make follower counts worthless.

“Whenever I lose Twitter followers I just assume Twitter was cleaning house,” jokes Friedman. “Oh I lost some followers. Twitter must be cleaning house. Always.”