What do you enjoy most about stand up?
I like the day. Once I started headlining comedy clubs I really got into the average day on the road. Wake up at noon in a hotel. Drink some coffee. Go sit in the hot tub. Head to the hotel gym. Take a shower. Walk to the show. Listen to some pump up jams. Sit in the back and watch the other comics. Listen to the crowd. Go up and do 45. Shake hands. Go out on the town with the comedy club staff. It’s really a great day. And then I get to do it again all weekend and then leave town.
It’s not for everyone, but it’s the most fun thing I can think of. It’s like being a politician who doesn’t have to actually do anything. I don’t have to go to work or make laws or keep promises. I just get to do the fun campaign stops and hang out. It’s really cool.
If only politicians were that chill. What do you enjoy least?
I would say the myths. There’s no constitution or Bible for stand up. We don’t really have a union or leadership or anything. We’re just a bunch of idiots. Comedians say something onstage or on a podcast and spread misinformation to all these hungry young comedians who soak it up. Some of it’s great advice but some of it sucks. You can get a bad piece of advice and live by it for years before you realize you were misled. Like this interview. Some idiot’s gonna read this and listen to what I say. And I’m just some guy. I got no degree. I don’t even read.
How is performing for TV different from other live performances?
Well, you have to stick to what you agreed to do. There’s not a whole lot of room for switching stuff up when Ford and Budweiser have to approve your jokes. But it’s a fair trade-off. The audiences are better than average and a lot of people see your set. It’s a crazy mix of art and ruthless capitalism and I’d like to do it every day.
How did you prepare for your first CONAN set?
I was flying blind, really. I had no idea how the process actually went so I just binge-watched Conan sets and tried to find patterns and see how they flowed. Then I would google people who did Conan and listen to them on podcasts. I heard Tommy Johnagin talk about doing a Letterman type set at the Montreal Comedy Festival because he knew the Letterman booker was gonna be there. So I did that but with Conan. And it’s crazy but it worked. The booker saw my set at Montreal and that’s the set I did on Conan.
What would you tell a comic trying to book his/her first show?
Write jokes. My first time I thought I could just “be funny.” It didn’t work. If you take some time and write some jokes with some set ups and punchlines, you’ll be way ahead of me. Also, lie to your friends. Sneak out and do stand up a couple of times without them so that when you invite them to your “first show” you’ll have some experience under your belt. I invited ALL my friends to my first show ever and a lot of them still don’t talk to me.
Can you explain your joke writing process?
I just write down whatever makes people laugh in real life. At dinner, at parties, etc. Usually 1 in 10 things that make my friends laugh will end up making an audience laugh. It’s not a great batting average, but it works a lot better than just writing jokes down in Microsoft Word and trying to recite them.
How did Deadliest Chef come together?
When Comedy Central started doing Snapchat sketches I didn’t really know what it was. One of my friends works there and she asked if I wanted to do it. I agreed to, but I thought it was gonna be me in my apartment making short videos. Turns out it was a whole production. It was insane. It was super fun and they kept letting me make them. Felt like I was really getting away with something. They’re super dumb. I intentionally made them very stupid. And it’s funny to see people online like “THESE ARE DUMB!” And I’m like, yeah. I know.
What’s your deal with margaritas?
It’s one of those things I started talking about because they used to be a guilty pleasure. They’re a silly drink. They’re a good mood drink. And when you’re a comedian your life is ridiculous. So all the things I used to be ashamed of aren’t so weird anymore. I don’t have to pretend to be cool. High school’s over. I can listen to Ludacris and drink margaritas and wear a Hawaiian shirt without waiting for someone’s approval. And it’s fun to order one at a bar because someone always hears it and goes “You know what? I’LL have a margarita, too!” Like they forgot they were allowed to drink them.
What makes a joke funny?
I think it’s something being wrong. Either you didn’t think something through, something’s out of place, or something’s morally wrong. Great bits usually sound like a TED talk from an idiot, or a political speech from a drunk. Just something isn’t right. That’s what makes them funny, to me at least. Other people disagree sometimes. People come up to me after shows and tell me I’m wrong about something and I go, “Yeah. I made all that up.”
Check out Caleb’s work at https://www.calebsynan.com/, on Twitter @CalebSynan and elsewhere on the internet.
Read more Writing Jokes on Twitter at @jokewriting