Make Sure it’s Funny: Comedy Writing is Hard

a microphone on a dark background with a little bit of backlit lighting
stand-up comedy mic

Comedy writing is hard. First of all, what’s funny is often subjective, which makes it especially tricky. There’s the ever-looming risk of the cliché. It’s easy to sound hackneyed, especially if you’re new to writing funny. And it can be discouraging when it isn’t as respected as “serious” writing, but then it’s also oh-so-golden when it lands just right.

Of course there’s a tiny urge to assert that if it’s funny to you, that’s good enough. But when timing, presentation, context, and a million other niggling little details are under a microscope, that assertion can feel decidedly less assured. Writing to inspire laughter is risky.


The American political satirist and journalist P.J. O’Rourke once said, “Being gloomy is easier than being cheerful. Anybody can say, ‘I’ve got cancer’ and get a rise out of a crowd. But how many of us can do five minutes of good stand-up comedy?”


I’m a huge comedy fan. I watch a ton of stand-up specials, the vast majority of my favourite TV shows are comedies, and I make an effort to get out to see live comedy shows – both local and touring – as much as I can. A well-crafted joke is a true work of art. And it’s especially exciting when it’s not playing to the lowest common denominator. Comedians deliver information through a clever medium that serves as social commentary and presents fresh perspectives. Multi-layered jokes engage your brain; then, when that callback comes it feels like you’re personally in on the gag. There’s almost a visceral payoff.

drag queens are the original roastersIn the past five years or so I’ve been attending an increasing number of drag shows in addition to the stand-up, sketch, variety, and even improv shows that have long been sprinkled throughout my calendar. Drag is exactly my kind of irreverent, and I find it wildly entertaining. Besides being hilarious, many drag performers impress by putting triple-threat entertainers to shame. Some performers lip-sync, sing, dance, do stand-up, improvise, choreograph, host, and bend-flip-and-stretch in amazing ways. And some do all this while also making their own elaborate costumes, styling hair and outfits, conceptualizing and applying truly fabulous makeup, crafting accessories, and even directing, staging, or designing sound and lighting. As if the “just make it funny” portion wasn’t difficult enough, right?


Roasting, a form of comedy particularly popular in North America, is one realm in which drag performers excel; some even say they’re the original roasters.


The popular 1991 documentary Paris Is Burning, which gave viewers a look inside the competitive ball culture of 1980s New York, declares that “reading is fundamental.” The close-knit yet vastly diverse subculture ruthlessly demonstrates how to “read” – a term derivative of “read like a book” that means to wittily criticize or expose a person’s flaws in an often exaggerated insult – without causing undue harm. Because drag performers and those adjacent are often from marginalized groups there’s a sense of “you can’t say that, but we can” in this type of roasting. It’s both fascinating and familiar, and I think people with siblings often understand the sentiment which makes sense since ball culture is based around houses that are akin to families. More mainstream roasts (like the Comedy Central variety) try to enlist close friends of the “roastee” in addition to seasoned roasters to mimic this feeling. Proximity also offers more intimate and sometimes shocking material while simultaneously protecting the relationship, no matter what’s said.

love to laughIt takes a special kind of genius to be truly funny.


I love watching someone perform their own material, sometimes tweaking it on the fly to adjust to an attentive or even a disengaged audience. It’s thrilling to watch and even better when I’m laughing.

Comedy writing is a team sport. Whether that’s a duo or an entire writing room, the goal is perfecting joke after joke. There are re-writes with punch-up writers and people brought in just to increase the funny. These writers are producing words in a form that can benefit from rehearsal, practice, and performance; delivery matters so much in this medium.

Whether comedy is being used as a tool for social criticism or to drive change, as a coping mechanism for grief or despair, or as a way to reach out and connect, its beauty still lies in its ability to entertain. Laughing is wonderful. Making someone laugh is beautiful. And that’s why I’ll remain a lifelong comedy fan. Even though writing something funny is really, really hard.

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