In advance of that appearance, Cayton-Holland — or hell, let’s call him Adam, since he was a staff writer at Westword about a decade ago — talked with us about his first writing gig, his comedy, his sister, and how it was to write about her and her passing. And also about Denver, the city he both loves and misses.
Westword: You used to write for Westword, and now you're being interviewed by Westword. Is that weird? Is this how you imagined it might be?
Adam Cayton-Holland: Ha! It's a little strange, I suppose, just because I know how the sausage is made. But you know, I used to read Westword growing up, so I had a relationship with the paper as a reader long before that. And I haven't written for them since 2009, so I guess I'm just happy to appear in these pages once again. I'm sure some guy at Chipotle is reading this right now, spilling dollops of wet sour cream onto my very words. And it’s good to have that feeling again.
How did you originally get started writing for Westword? Any favorite memories of your time here?
My buddy Monty convinced me to enter an essay contest Westword was running; "Denver, Why I Love Her." I was living in Chicago, taking classes at Second City and trying to figure out what I was doing with my life. They liked my submission enough to publish it, and Patty [Calhoun] asked me if I had any interest in freelancing. It was the biggest lead I had going professionally at the time in any field, so I moved back home, started substitute teaching and freelancing, and then I started standup. All in 2004.
Any standout recollections from your tenure here?
Many. Making vlogs for the web with my buddy, former web editor Sean Cronin. We didn't know what the hell we were doing, and they were really funny and weird. My friend Jim Hickox helped out a lot. I used to write a humor column called "What's So Funny?," and one week I decided to take full advantage of the Rockies promotion where if they score seven or more runs you get a deal on tacos at Taco Bell the next day. The deal was that the following day you could get four tacos for a dollar at any Taco Bell between 4 and 6 p.m. So I set out on this mad dash to get as many tacos as I could in that window. It was a shit show, just me speeding all over the city looking for Taco Bells. I got something like 32 tacos. I came back to an empty office to type up the article, and I left a taco on everyone's keyboards so they would have a delicious treat the following morning. But mostly I remember smoking cigarettes in the back alley with then-music editor Dave Herrera and food critic Jason Sheehan. We would just chat and laugh and laugh back there. It ruled.
Your new memoir Tragedy + Time is part autobiography, part tribute to your sister Lydia, part meditation on loss. How was it to balance those three elements in the writing? How tough is it to write about mental illness and suicide and family, and also write about comedy? Or is there some sort of undercurrent that all those things somehow share?
It honestly wasn't something I thought about during writing. I was just getting it all out. This book was an extremely necessary act for me. It was the way I processed all of it. It was a catharsis. So I just kind of vomited all of it onto the page — the good, the bad, the devastating, the mental illness, the death, all of it. And I think that feels really true to life. Or as I experience it, anyway. So perhaps that's the undercurrent. That it can all happen at the same time — not in some neat, compartmentalized way. I think that rings true to how a lot of people experience overwhelming things.
The book grew from that, but also from podcast appearances I was making. My lit agent heard about me through comedy podcasts, went back and researched me, found some of my writing — including that article — and called me out of the blue and told me I should write a book. So I give a lot of credit to him for planting that idea in my head. I was just writing as a way to process grief, which was why I wrote that Atlantic article. What happened to Lydia was so profoundly traumatic for me, obviously. It dominated my thinking, and I wasn't talking about it on stage, so I had to write about it. I've always been a writer first, comic second, so I think I needed to write about this so I didn't feel any pressure for it to be funny. Nothing was funny about this. I wish I was the type of person who just processed things internally, but for better or worse, I'm this creative person, and I have to get this shit out in some form or another.
Your acknowledgments section ends the book — sort of perfectly, I think — with a short personal note from you to your sister. What do you imagine Lydia thinking of this book? What would her response be to you writing it for her?
It's my sincere hope that she would like it. I tried very hard to not make this book overwhelmingly about her death. More about her life. Because Lydia was absolutely incredible. So smart, so funny, so weird, so beautiful and completely herself. Just an utter individual. I consider the time I had with her a gift. I cherish it. So I want this book to serve as a tribute to her. I think she'd be honored and then quickly say something self-effacing and get out of the spotlight. Then we'd obsess about it later in secret.
The title Tragedy + Time is obviously based on the old-saw definition of comedy (apocryphally credited to everyone from Carol Burnett to Steve Allen to Mark Twain). Speaking comedically, do you subscribe to that idea?
It's funny — I don't. I remember someone did an interview with me before Lydia's death. And their question was basically about how I come from a normal, good family, I don't seem all that fucked up, how am I possibly funny? Comics have to be tortured, dark geniuses, right? It's such a lazy trope. Comics are sensitive. Comics are observant. Whatever way you arrive at that place is simply a means to an end. Whether you're a comic because you're trying to make your distant father finally pay attention to you, or whether you're a comic because you were a wallflower in middle school who watched everybody from afar, one is not worth more than the other. Of course, now I have enough pathos to drown a graveyard, so do what you want with that answer.
In the book, you talk about David Letterman being your "own personal Jesus" and writing your own Top Ten list. What were some of your other favorite bits that Letterman did? How instrumental was Dave to the comedian you've become?
Man, I loved Letterman. Just his odd sayings: "Uh, you got any gum?" He would just say that randomly in the middle of a monologue. Adopt a hick accent and go for it: "Uh, you got any gum?" So funny and weird. I loved when he sent Mujibur and Sirajul around the country. First time I went to NYC, I went to their shop, then Rupert Jee's Hello Deli. They were like celebs to me. Dave was really tuned into the oddity and humor in everyday life. I really like that. Who cares about him interviewing celebrities? Give me a shot of him picking something out of his teeth for effect. That kills me. Uh, you got any gum?
And Dave led me to Conan led me to The Simpsons led me to The Onion led me to Mr. Show led me to standup. They were all huge for me.
Your TruTV sitcom, Those Who Can't, is based in Denver, a city you grew up in and where you still live. Denver gets its share of jabs, politically and socially and the like — how do people in the city respond to the show?
People in Denver love it! Although one night at my friend's bar, some chode teacher from Creek was drunk and got in my face about how we're doing teachers a disservice by portraying them as inept. It was like, "We're portraying bad teachers. It's right there in the name: Those Who Can't." My friend threw him out of the bar. I think good teachers don't worry about negative depictions, because they don't see themselves in our idiot characters. I also think good teachers — get this — have a sense of humor! You have to. Sometimes groups of teachers will organize outings to live comedy shows of mine, or Ben Roy's or Andrew Orvedahl's — my cohorts in Those Who Can't — and nothing makes us happier than that. Those are the people out there fighting the good fight and being woefully underpaid for educating our children. They need a laugh more than anyone.
But, yeah, for the most part, people in Denver really like the jokes we make about the city. A lot of them aren't even jokes. Just local references. They're more shout-outs as a form of love. That's why our characters drink at the Lion's Lair. We all started comedy there together.
I don't know if I drink there free or not. Hey, Lion's Lair, do I drink free at your place? At the very least, how about a free T-shirt?
The book talks about Those Who Can't a bit — and portrays your first meeting with co-star Ben Roy at the Red Room. You refer to yourselves as "two young Skywalkers." If there's one criticism I might make of the book, it’s that there aren't nearly enough Star Wars metaphors. Since you were born in 1980, you were only three by the time Jedi was released, and grew up in what was the doldrums of Star Wars fandom. Did you manage to still become a fan? Or am I making far too much of that reference?
[Laughs.] Man, I wish I could punt this question to Andrew Orvedahl. He is a Star Wars FANATIC. He would go on for days and days in answer to this question. You ought to see his house: so much Star Wars shit. Like expensive, geeky Star Wars shit. A Boba Fett helmet; a LEGO X-Wing. It's clearly an obsession. I like Star Wars, but alas, I'm no fanatic. I see all the movies as they come out, but like ten, twenty days after they've been in theaters. By myself. In the middle of the day. Like a fucking creep. That said, Rogue One is the best thing to come out of the Star Wars universe in a long time. I know enough to know that.
As a lifelong resident of Denver — and now an authorial expert on tragedy and time — what do you think that Denver's lost over the years that we could start to find funny today? And what does the Mile High City have to work to preserve, so we don't have to laugh about it later?
Denver's lost a lot. It sucks. Sometimes I open shows by asking, "Hey, everyone, what part of your childhood was torn down this week and replaced with mixed-use condos?" It's sad. We're losing a lot of character, a lot of charm. It's still there, of course — you can't ruin our beautiful old neighborhoods — but you have to look for it harder. I used to be obsessed with Beatnik literature — how on-brand! — and you read a lot about the alleyways and empty lots of Denver. The empty lots are all gone. The alleyways remain. Walking home from a bar at night, I'll often take the alleys. It's not hard to imagine the Denver of old there. But Denver has lost affordability — and the glorious artists and weirdos that come with that. Not a lot of great art coming from the legions of tech-bros who think Denver came into existence the day they walked into the LoDo Whole Foods.
Anyway, I sound like the old hipster ranting at the bar, so I'll shut up, but to anyone out there who has money and is looking to start a business and cash in on this Denver boom: Do it in an old building. Save old buildings. Don't tear them down. And for God's sake, some affordable housing. This city is going to lose a lot if it's just rich and white. We need look no further than the White House to know how fucking evil that is. Oh, and if you're thinking about moving here, don't. It snows 300 days a year. You can't breathe at this altitude. The Rockies are full of dangerous prospectors and grizzlies, and pot's not legal. That's just a rumor.
Adam Cayton-Holland will read from and sign his new memoir Tragedy +Time at the Tattered Cover, 2526 East Colfax Avenue at 7 p.m. Tuesday, August 21. Signing-line tickets are $26 and include a copy of the book. Find out more at tatteredcover.com.