5 Lessons Learned As A Freelance Comedy Writer

1 Titles are Everything

A couple of years ago, I sold a piece titled “Mr. Rogers’ Neighborhood Association: July 2020 Meeting Minutes.” Once my brain stumbled upon the idea of combining Mr. Rogers’ Neighborhood and the busybody horrors of any neighborhood association, I knew I had a sale before I even wrote the story.  

If you’re pitching a funny article (as opposed to single jokes), the title needs to get a laugh.  

2 Volume, Volume, Volume

Before I even could get a toe in the door, I was asked to submit a list of 50 potential jokes to make sure I was worthy of even being introduced. Basically, it was an audition to get the audition. I got to work and a few days later, I sent over my list of 50 gags. They likely weren’t even great jokes -- but by gum, there were 50 of them.

I got the endorsement, my jokes made their way inside the mysterious comedy machine, and I was accepted as a contributor. I later learned I was the first person that my inside source had ever recommended, even though he’d been asked several times for similar favors.

Why me? The “try giving me 50 jokes first” qualifier had weeded out all of the other aspiring jokesters – he had barely considered that someone might actually sit down and write them.

In my early days of submitting jokes to that website, I always tried to write twice as many as requested. (I didn’t turn in double, that would be a no-no -- I simply submitted what I judged to be the top half of what I produced that week.) My reasoning was that the more jokes I wrote, the better the chances that three or four might actually be good enough.  

Long story short: The more you write, the better your chances of striking gold.

3 Expect (and accept) rejection.

That’s because the site also believed in the Volume, Volume, Volume theory -- if you need 10 jokes, then start with 250. The best 10 (or about 4%) are likely to be pretty damn funny.

So … good for the comedy site, tough for you. Selling 4% of your work means getting a “no” 96% of the time. You’ll likely do better than that -- but do the math.  Selling 40% instead of 4% -- ten times better! -- still means a no more often than a yes.

And that’s OK! A “no” doesn’t mean you wrote a lousy joke. It could mean that your joke is too similar to nine other punchlines already under consideration. Or your bit is cerebral when the buyer is looking for something silly. Or the editor is exhausted and you caught her on a bad day.  

So remember: Just because a joke (or article or whatever) isn’t right today doesn’t mean it’s no good.  Just get back to it.

4 Find an oddball way into topical subjects.

Here’s the problem: Rooms full of comedy writers are working on one-liners about that same press conference stumble for Jimmy Kimmel, Jimmy Fallon, James Corden, Steven Colbert, Trevor Noah, Samantha Bee, and all their late-night brothers and sisters.  And before those professional yuksters get a chance to deliver the goods, an army of Twitter comedians have already weighed in with their funny takes.  

Maybe you’re one of those Twitter comedians!  Go nuts!  But you’re not getting paid for those gems except in Like endorphins.

So if you want to sell humor about Biden’s press conference, you’re going to have to work the margins. Maybe you’re an admissions officer for Joe Biden’s School of Famous Talk Good. Maybe it’s conservative and liberal gremlins wreaking havoc inside the podium. Maybe it’s Biden deciding to do an unboxing video for his next State of the Union. Hopefully, it’s a better idea than any of the above.  But you get the idea -- go after Joe’s oratory skills but maybe steer away from a specific incident that will be joked out before you get to sell yours.

5 Make comedy friends.

Writing funny is more important than who you know -- but who you know doesn’t hurt.

We’re not suggesting some Machiavellian scheme where you sidle up to funny people in an attempt to overthrow the comedy castle. But just as in every pursuit, building strong relationships can really help you find opportunities to write comedy. The fellow joke contributor you befriend today may become an editor or talent coordinator tomorrow -- or vice versa.  

If your new friends already trust your comedy writing abilities, you’re likely to be one of their first calls when they need help on a new project. And vice versa.  People like to work with their friends, what can we tell you? Look at performers like Tina Fey and Amy Poehler. They became friends when they were both unknown improvisers in Chicago, and they’ve been casting each other in comedy projects ever since. 

Bonus:  You’ll share a common interest!  You both like writing jokes!  And now, you’ll have someone to commiserate with when SNL rejects your writing packet. Maybe they’ll even bring snacks.

For more ComedyNerd, be sure to check out:

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Top image: Andrea Piacquadio via Pexels