How To Win Portland’s Funniest Person

It’s time once again for all the comedians in town plus the funny guy from Toast Masters to try to impress a group of local DJs. If you’re interested in summitting that particular mountain so you can have a mediocre regional credit, then you’re in luck. I’ve developed a foolproof system which I will provide free of charge and then mute all the comments on.

But first, a word of warning: you shouldn’t want to win. It’s not nothing, but it’s way closer to nothing than it seems. People who don’t respect you now, won’t respect you if you win. And that includes yourself; you’ll feel awesome for a week, okay for a week, and then the black hole in your psyche will open back up and return you to the darkness you’ve called home for as long as you can remember. The money isn’t life changing. Month changing, sure. But that’s about it. You might buy your friends pancakes, get a new pair of sneakers that make you feel like a champion when you wear them, and pay rent. And then there’ll be no money.

Oh but the podcasts you’ll get invited to! And a local TV show nobody watches will ask you to play a game where they hit you in the face with a pie because they really get comedy. Make sure to report all that exposure on your taxes. Then never tell anybody outside of Portland you won because saying you’re Portland’s Funniest Person in New York is like putting your SAT score in your Tinder profile.

Also, when you win a contest, 7 to 12 comics you like and respect just lost one, so don’t expect the jubilant atmosphere you’d dreamed of. Your friends are happy, but it’s already 11pm on a Wednesday and they’ve got to get to bed. It’s pretty bitter sweet. Maybe competitive art is stupid? Nah, that can’t be it.

Which isn’t to say you shouldn’t do the contest at all, you just shouldn’t care about winning. Not winning contests over the years has gotten me way more stuff than winning them. A great comic told me, “If you win, it’s a contest. If you don’t, it was a festival.” So try not winning and still using it as an opportunity to do a good show or three and hang out with people you like and get a good tape and meet some fake industry people. Try losing and still getting stuff. That’s a good way to go. I highly recommend that.

Okay, but if you absolutely must try to win, fine. Go for it. And you might as well go in with the best advice you can have. So here it is.

1) Lose a bunch first. On average it took me 7 tries to win PFP. I recommend doing less well than you’d like each time, but a bit better than the year before. Also a bunch of judges come back each year so having them see you multiple times is probably helpful. Be nice to them when you see them in the hallway. Maybe even agree to go on their dumb radio shows for no money at 6am.

2) Don’t do your best jokes, do the best parts of your best jokes. Pick your best possible 10 minutes and run it. Then take half of each joke, so it’s only the part that really bangs.

3) Do a set that works for a contest. You’re doing a short set in a fuck pile of similar short sets, so the rules are a little different from doing a bar show. You gotta get them quickly, make them like you enough to vote for you, surprise them so you deserve the win, and leave them at your peak so they’ll remember you later when they’re tallying up their scores. Start with your shortest joke. Get a laugh in like seven words. Then follow it with a one minute joke with three punchlines. Now they’re paying attention because you seem to know what you’re doing. Then take two minutes to do a joke or two that are autobiographical, to make them care about you and to stand out from the other fucks. Then do two minutes taking them somewhere they weren’t expecting. End on a callback that demands an applause break. Definitely say something that they can agree with because they’re forced to applaud, but make sure you’re not actually challanging them.

Here’s a graph of the energy your set should have:

__-____-__–__–_–_____-___–__–||||||–________—_____–____–||–||–||||||||||||

4) Do a set that works for a contest audience. These are normal ass people. Most of them got a baby sitter and agreed to come support their friend in the only comedy show they’ll see this year. They don’t watch movies, they don’t read Reddit. I’m not saying to be clean, definitely don’t do that. But if you’re going deep on stuff that other comics laugh at, it’s probably too dark, referential, or based on obscure serial killer conspiracy theories for the audience to give a shit about it. Compromise your art for five god damn minutes and talk about something normal people can laugh at.

5) Practice your set a bunch. Call in every favor you’ve built up around the city over the past seven years of failing. Use those guest sets to run your contest five as many times as you can. Record them and listen back. Identify weak points and write fixes. Lather rinse repeat. Over and over. Until everybody is sick of your set, including you. Use mics to test smaller parts of the set. Get no laughs because everybody went outside to smoke right before it was your turn. Get discouraged.

6) Take a week off. Do new jokes. Do jokes you like but would never do in a contest. Fuck around and remember you like comedy.

7) See that your prelim is coming up in a couple days. Get freaked out again. Run the set one more time. Feel better?

8)

9) Get lucky on the draw. If you’re too early or too late or you go when the judges are drunk or just went to the bathroom, then you’ve got no chance no matter how good you are. So make sure you’re lucky or you won’t have a chance. Speaking completely hypothetically, one could pull bullet in the finals of the Boston Comedy Competition in 2018, which is only 8 people and first prize is $10k and second prize is not-a-god-damned-thing and then one might HYPOTHETICALLY wonder forever if getting that bullet might have cost one $10,000 which really would be way closer to life changing than PFP’s piddly prize money and could have bought WAY MORE pancakes and sneakers. Hypothetically. The point is there’s a ton of luck involved in contests so make sure you’re lucky.

10) Manage your dumb nerves before your set. Plan a busy day before the show so you’re not thinking about it. Then, make a playlist of music that makes you feel how you want to feel right before you go on stage (different depending on your style: happy, pumped up, chill, whatever) and listen to it before you go up instead of hanging out with people. This will keep you from making friends and hanging out with them, which would definitely be more helpful in the long run than a stupid contest, but it’ll make you feel better when you step out on stage, which is what you want since you decided you wanted to win against my advice.

11) Manage your dumb nerves after your set. Go to a part of the building where you can’t hear people crushing on stage because that’ll be discouraging (“Oh man, I didn’t get laughs THAT big. I’m fucked.”) despite it having no bearing on your actual set (laughs aren’t judges, and you can’t compare laughs from off stage to how they feel on stage). Headphones in the 9th Ave Lounge work well, or go to your car or go for a walk. Seem like a weirdo to the other comics, but feel a bit better.

12) Be nice but not like weird to your host. This won’t help you win but I’d appreciate it anyway.

If you follow that, you’ll definitely win. If you fuck up one of the steps (like if you don’t get lucky), then you won’t win. And if you don’t win, CHILL THE FUCK OUT ABOUT IT. Like I said, it’s not important. But even if you don’t believe that in your heart, people will remember when you were a douche about the whole thing on stage or on social WAY LONGER than they’d remember if you won. Whatever dumb sad thing you post will be screen-shotted and shared in group texts for literally years. So even if you think it’s the end of the world, you can still win at losing or lose at losing. That’s totally up to you.