How to make it in comedy

Probably don’t bother.

When you image of “making it” in comedy, you might imagine Jerry Seinfeld. Yellow legal pads and nightly stand-up sets at the Comedy Store. 

But there's this whole other realm — the realm of improv and sketch comedy — where people like Will Ferrell, Kristen Wiig, Will Forte, and Jason Sudeikis came from. A different breed. Someone once told me, “If stand-ups are wizards, then improv people are snow-elves.” I don’t know what that means, but it’s provocative.

The most prestigious place to try your hand at this kind of comedy is a school in LA called the Groundlings. Named for the people who would stand on the ground (hence “groundling”) for a pittance to see a play. Low-class, no-filter characters came out of the woodwork to watch a raucous Shakespeare play, throw rotten tomatoes, and hoot and holler. They encouraged the aristocrats in the upper rows to holler along, laugh, and cheer. A welcome release valve for the stodgy elites. The Groundlings made the shows fun. Their absence is why, for the most part, Shakespeare is not fun today.

At The Groundlings, you go through these Scientology-like levels, up through the ranks, where at each level you can be kicked out and never get another chance. You're judged by a mount Olympus of famous and semi-famous comedians. Each of the cast is a co-owner of the theater and votes on who gets to join their legion.

Once a Groundling, you’re a Groundling until you retire, which could be a decade or more. There are only around 30 of them. So, for a bright-eyed young student, the chances of becoming a Groundling are probably something like 1 in 100,000. And many try, dropping thousands of dollars in the school.

This happened to me. I went through all the levels of the Groundlings, making it up until the second to last. 

I can chalk up my failure to a problem with temperament. Too moody, too intellectual to truly let go into character acting and buffoonery – to truly transcend into hallowed comedic halls. But I liked it. If life were college, comedy would be my minor. I think it rounds me out. It makes me careful not to take myself or my ideas too seriously. 

Last night I went to my friend's show. Luckily for me, he was genuinely the funniest person on the stage. Sitting in the semi-dark between sketches, I looked around at the sold-out crowd and wondered, what are we doing here? 

The characters (it is “character-based comedy”) are always low status or low status aping high status. Not to murder to dissect, but I think when we recognize an abandoned and disliked version of our own personality, we light up and release a cacophony of catharsis. Laughter, hopefully, lets us know that our shadowy and repressed foibles are A-OK in the grand scheme of things.

As an aspiring comedian, first, you have to learn how to make a fool out of yourself. Not only accept the things about yourself that you don't like, but put those on display in caricature for others to gawk at, laugh at, and take relief in. This is a humbling experience at best and a humiliating experience at worst. It scares most people away from even trying it. Your friends will say terrible things like, “You’re so brave.”

At the same time, the Groundlings itself is a brutal competition, everyone quietly vying to be the funniest. It’s an upside-down kingdom. Whoever is willing to artfully debase themselves the most courageously is paradoxically raised to the highest. Bad performers don't have a good sense of what is truly embarrassing about themselves. So, they pantomime some image of what they remember to be funny. And this trickery almost never passes the smell test. Audiences cringe.

Wayward, maladjusted people trek to LA by the thousands every year. They hope to redeem their exclusion by exploiting their character defects in a way that is healing for others. Mostly, they fail because they want to glorify themselves, which is at odds with making a fool out of yourself.

Traditionally, actors and comedians were the lowest of the low; the carnies, the clowns. Normal people think comedy is a high-status because all the comedians they know are famous. They don’t realize that we've elected a microscopic minority to be kings of fools. Those crowned few redeem the character defects of millions. Adam Sandler, for one example, showcases an archetypal man-child, giving relief to mad-children the world round.

You make a deal with the devil: exploit your character defects for the amusement of others, they become your livelihood. From that point on, your career hinges on you maintaining what is wrong with you. And so many comedians wallow in alcoholism and addiction and depression. They rightly fear that getting better would make them not funny.

Jim Carrey is an interesting example. In the 90s, he drove to a mountain top and swore he would become famous. With the courage of Zeus, he dove headlong into his previously repressed defects. His characters were idiots with miraculous, buffoonish confidence. As a result, he was crowned king of the fools… until it almost destroyed him. His girlfriend died by suicide and was on the edge himself. He felt trapped by the character “Jim Carrey.” Needing to escape it, he abandoned his old persona. He became a pseudo-philosopher and painter they occasionally bring on to talk shows to pontificate with his beard on. That was enough to save his life – but he’s no longer funny.

I think of Theo Von or Dax Shepard, who got into 12-step recovery programs. While they are probably less funny than when they were alcoholic youths, they manage to retain enough of the spark to keep both their careers and their life. They often talk about how difficult this balance is.

Other comedians will take their shtick right to the grave. Robin Williams comes to mind. You can see his attempt at the transition – the attempt to do serious acting – to escape the character defects, to heal. Evidently, it was too little, too late.

When you're taking classes and performing shows, the idea of “making it” is halcyon. But nobody takes a moment to just look at the lives of those who make it and think, do I even want that? Mostly, they either burn out or they spin their wheels for decades – stuck in a loop of the same foibles, like Groundhog Day. You can see the “Waiting for Godot” in their eyes.

I had a teacher who told me, "This is everything I wanted, but it ended up being a trap." He had a small role in a famous sitcom. His claim to fame, everything he wanted when he was 20, became a sad replacement for a normal life by the time he got into his mid-40s.

They talk about this on their podcasts (Theo and Dax) to an audience who can live vicariously through all their fame and mistakes. Maybe they had dreams of trying comedy but never did. Now, they can rest easy that normal was the right answer all along.

Creative work is a revelation of the divine through a broken vessel – a crack filled with gold. If an artist can learn the lesson of their own art, they would no longer make the art. The overwhelming desire to differentiate themselves from normalcy, from others, from connection, from family… would vanish.

But artists, especially successful ones, fear normalcy more than anything.

Kierkegaard said that poetry is all the work of the devil – himself a poet. I don't know if that’s entirely true. But there is some truth to it. A happy person would not try to immortalize their self-worth. But, at the same time, Dante’s walk through hell (and others like it) brings a texture to life that we wouldn't want to live without. In the Miltonian tradition, all the works of Satan’s darkness are finally redeemed in the light – all part of the plan. 

So, to the person who wants to know how to make it in comedy, I would say: you don't really want that. 

But if you're truly determined, as Bukowski said, if you must write, if you must perform, if you must make jokes, then do it. Burn yourself alive doing it. Because if you're going to do it anyway.

No half measures are going to work. If not trying would mean regret for the rest of your life, God be with you.

Matthew Perry prayed, "God, I'll do anything if you make me famous." Look at the aftermath. Weigh it for yourself, then make the decision one way or the other. Once the decision is made, never look back. Do it with reckless abandon. Do it even if it starves you because that is what you were going to do anyway.

But if there's any doubt, if there's any hesitance, if you think you would be okay with a normal life, then I would say, do that instead.