It was Samantha Weiner’s idea. She’s an editor at Abrams Books. She told me she would give me money to write it, and so I said, “Okay. I will write it in exchange for said money.”
Which song did you most enjoy deconstructing?
The DMX chapter was probably my favorite one to write.
Why do you keep a newsletter?
I haven’t done the newsletter for about nine months now. I started it back when I started it because I wasn’t writing anywhere and I wanted to feel creative again. I’m glad so many people liked it. Last I checked, it’d gotten over 30K subscribers in just a few weeks.
Why do writers become writers?
I don’t know why others do it. I did it because I needed to make some extra money.
How do you pick what topics to cover at The Ringer?
We have a machine at our offices called The Idea-tron 2000. You just plug in three different keywords and then it spits out an article premise. For example, two weeks ago Ityped in “Isaiah” and “plane” and “shark” and then the machine told me to write this.
How has your time at Northwestern influenced the rest of your career?
While I was at Northwestern, I did a number of things that regularly put my work in front of my peers. In particular, I edited the humor magazine and I drew a comic strip for the school paper. I knew my audience was smart and sophisticated, and I would hear (directly or through the grapevine) whether my work was hitting or missing. I had a lot to learn, and still do, but some part of me is still imagining that Northwestern audience out there.
Are single-panel cartoons more difficult to produce than cartoon strips? (Why or why not?)
In retrospect I think writing the comic strip was easier than coming up with single-panel cartoons. Over my four years drawing “Banderooge” at Northwestern I developed a cast of characters, each with his or her own voice. To some extent the characters began to write the strip themselves because of the ways their desires clashed.
In creating single-panel cartoons (I hate the term “gags”), you are dreaming up an entirely new scenario each time, and trying to imbue the players with enough signals so that the humor comes through: This kind of guy saying thatkind of thing to that other sort of person.
What makes a single-panel cartoon particularly effective?
My favorites (whether my own or by others) have an incongruous visual element that is resolved by the caption. Reading a cartoon happens over a number of almost imperceptible steps. First, because the visual elements register effortlessly, I think you glance at the drawing just long enough to think, “Oh, it’s cavemen admiring a cave drawing” or “Oh, it’s two frogs, one of them has a paddleball,” but you don’t understand what you’ve seen until you read the caption, which ideally should cause you to look again at the picture. And then the incongruity in the picture should cause you to want to read that caption again to enjoy it more fully. Back and forth and back.
Do you have any themes or motifs that you especially enjoy?
I think I’ve sold more cartoons about cavemen than any other topic, so I must find them a rich area to contemplate. Of course, a caveman cartoon isn’t usually about cavemen at all. It’s about relationships, or snobbery, or whatever — you’re just presenting it in a caveman motif.
I do like to write cartoons about childrearing. But again, that theme is woven into cartoons that might appear to be about bullfighting or evolving fish or what-have-you. I don’t have a ton of drawings depicting Mom and Dad raising the children.
How did Puzzability first come together?
My first job out of Northwestern was as an editor at Games Magazine. This was really a dream job for someone like me. That magazine was an extremely creative, playful publication with a staff that rivaled The New Yorker for wit and intelligence (they had no business hiring me; I had never written a puzzle in my life). Some years down the road, the magazine fell on hard times and many people associated with it scattered to the winds. I reached out to some of them to form our own puzzle-writing company. I’ve been lucky in that I’ve always worked with people who pushed me to stretch what I could do.
I’m no expert. But I know when I’ve done something good, and so instead of your question I’ll answer this one: “How does one get to be someone who can write a good puzzle?” It’s a craft like any creative endeavor. You work at it constantly, you develop a vocabulary of ideas you’re comfortable with, and you combine those ideas in new ways just to see where they take you.
An odd thing about writing a puzzle is that you need someone else to test-solve it to make sure it works. If it needs refining, your tester (which in my case would be one of my co-workers) needs to retest it “dumb” — that is, pretending that they don’t already know the solution. Those notes, and that refinement, help you anticipate problems for next time. Puzzle writers want to give their audience just enough to solve the puzzle, but no more than that.
How cool was it to work on Mr. Robot?
Recently Puzzability has worked on a number of cutting-edge projects; one of them was a Mr. Robot tie-in book. The project was very cool to work on, particularly when we got the call, because we were told the season’s big reveal before anyone else. If you watched Season 2, you know that Elliot was keeping a diary while he was in prison. But meanwhile his alter-ego, Mr. Robot, was trying to break him out.
Elliot was unaware of the plans of this other part of his psyche. A writer on the show’s staff wrote the meat of the diary, but Puzzability was brought in to craft hidden messages that Mr. Robot was sending to, and receiving from, the outside world. They had to be accessible enough for readers to find them, while being so well hidden that Elliot wouldn’t recognize them as codes. And Elliot is a brilliant hacker, nobody’s fool, so it was a fine line to walk.
The book was produced to look exactly like a composition notebook with pencil handwriting inside. But there are also tipped-in items that look like prison artifacts, and we created many of those. One of them is a photocopied list of bible quotations that Elliot was given in his mandatory prison bible class. There’s a code hidden in that, but Elliot just tucked it into his notebook and never gave it a second look. Mr. Robot figured it out, and so did readers.
That is awesome (thank you for sharing). Generally speaking, what makes for a good work space?
I’m the wrong one to ask. I feel like I can work anywhere. My puzzle work is definitely augmented by computers and occasionally graph paper, but a lot of the noodling (and cartoon-writing) actually happens while I’m walking. It’s good to have the Notes program on my phone for ideas that have to be written down. I don’t rely on having a clean surface or perfect silence, although yes — I do prefer those to their opposites.
I also just grab the blank side of scrap paper to work out ideas for cartoons. I used to do them in sketchbooks but they began to feel too “precious.” I prefer the throw-away nature of working on scrap paper. It’s liberating.
Why do you think cartoonists become cartoonists?
I don’t think that cartoonists ever decide to become cartoonists. I think they just don’t decide to become something else. I think that when we are little we are instinctively creative and open about the world, and we can’t draw all that well, and we think the world we see is confusing and adults are dumb, and all that stuff. And we simply continue along that path until we learn how to draw better. Then we’re cartoonists.
What makes you laugh?
Something really, really clever. It doesn’t even have to be funny per se. But if it’s just so carefully thought-out and well-realized that I never could have thought of it, it’ll elicit laughter. From a Buster Keaton sight gag to a wonderful anagram. It tickles my brain (I don’t necessarily laugh out loud, although that happens, too). As a cartoonist slash puzzle-writer, I get those reactions all the time. Nice way to spend the day.
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
In morning radio I had to do prank calls just to keep my job. LOL ended up getting pretty good at them.
Have any of your experiences in radio informed your style as a comedian?
Morning radio only made me more cognizant of making sure that I can simplify a premise as quickly as possible. In radio you aren’t given a lot of time to set up a story so the quicker you can set up the story the more time you have left to tell jokes off it.
How is stand-up in the south different from stand-up elsewhere?
In the south stand-up is more laid back. As a comedian it’s harder to get stage time because there aren’t as many clubs. So, as a comedian coming up in that region, stage time is much much more precious.
What makes for a great writers room?
I think diversity and anyone not afraid to push back against other people in the room is important. An array of views is always a good thing.
What do you enjoy most about working at The Daily Show?
I enjoy how fast paced things are at The Daily Show. And how quickly an idea can go from inception to being on the show nine hours later that night.
What’s your general process for coming up with new material?
I find things that bore me and indulge myself in them. My mind then wanders to other places and the creativity flows. Also I like to do things that annoy me because that state of mind help me create.
How did you become a Cubs fan?
Growing up in the south the Cubs came on TV a lot. The Cubs and the Braves. So I chose Cubs.
What makes a joke funny?
People laughing. That’s a tough questions to answer. Sorry.