Adam Cayton-Holland is an excellent human. I first heard about the actor, writer, comedian and author years ago when the Denver comedy scene went through a significant phase of growth, sending various performers forth to Los Angeles and New York where some attained further success. Cayton-Holland, Andrew Orvedahl and Ben Roy were the prime examples of hometown boys hitting it big. Their live comedy show, The Grawlix, became a requisite stop for touring comics going through Denver. It was particularly beloved by comedians who emerged from the alternative comedy scene that had its origins in New York and Los Angeles in the 1990s.

I started in stand-up and sketch in New York in 2005 and got into storytelling, radio, and acting a few years after that. I can recall chatting with friends in New York when we heard there was a flourishing scene in Denver. We were all surprised. Part of that was snobbery, and the delusion that New York City is the only place that matters, maaaaan. (This bubble pops soon enough, if you’re smart. Then you get rich, inherit Grandma’s apartment, go into tons of debt, or move.) But to be fair, Denver hadn’t exactly been a major player in the comedy world for long. It drew my interest, as did these much-praised mountain jester weirdos about whom I kept hearing such good things.

When I became an author for the first time in 2012, I wasn’t able to make it to the Rockies on tour. But when my next book came out, I made sure to hit Denver. First, though, I contacted this Cayton-Holland dude I’d heard so much about.

“You gotta hit up Adam,” people said. “Adam will show you around.”

“Oh, Adam’s a dope dude. Go find him and ask him about restaurants.”

“Adam can tell you about shows.”

“Adam will hook you up.”

“Do you need a place to stay? Ask Adam. He’ll know.”

I was like, “Who is this father figure/tourism bureau chief/comedy hero on whom some of these people clearly have a talent crush? I will find him and ask him where the best burrito is.”

Hey look, it’s Denver circa 2015! Photo courtesy of author.

He and comedian Mara Wiles were kind enough to tell stories to open for me on my stop at an incredible bookstore in town.

In addition, Adam gave me a fantastic tour of the city that made me realize he has a future in tour guide life if this whole successful actor/writer/comedian/producer/author thing starts to bore him.

Cayton-Holland, Orvedahl, and Roy had recently developed and filmed a pilot for Amazon that was later picked up by TruTV. That show, Those Who Can’t, is heading into its third season.

In the background of this success story lies a tragedy, and it’s at the heart of Cayton-Holland’s debut memoir, Tragedy Plus Time: A Tragi-Comic Memoir. His younger sister, Lydia, died by suicide in 2012, shortly after Cayton-Holland made a successful debut at the prestigious Just for Laughs Comedy Festival in Montreal. He discovered her body and wrote her eulogy, and as his close-knit family grieved, they encouraged him to keep a scheduled trip to Hollywood on the books. In the memoir, he writes of the insanity that comes when tragedy and victory are paired so closely together:

I kept going to meetings. Including one with Amazon. They liked our script enough to give us money to make a pilot. In Denver. Just like I always wanted. So there was that. I called home and let my family know. They were thrilled. And proud. I had sold a TV show. This was a worthy distraction. The trip could be called a success.
I was elated. And I didn’t care at all.

You can find adapted excerpts at Vulture and the New York Times and Good Housekeeping. And you can also follow him on Twitter and read this Q&A.

Sara Benincasa: How big of a role does the city of Denver play in your writing for the stage, for your show, for this book, and beyond?

Adam Cayton-Holland: Denver’s always in the background for me. It’s where I set everything I write, it’s where I live, it’s where I keep coming back to. As a kid Denver felt like this dusty little cow town and I always wanted to get out, but the more I left, the more I kept wanting to come back. There’s always the pull of the coasts and I think I felt that, but as I’ve gotten older, I feel the pull of Colorado all the time. Now I feel completely wrapped up in it. Denver has matured into this incredible city and I feel lucky to in some small way to be one of its voices.

When you write something that deals with serious and painful subject matter, do you ever find yourself reaching for a joke as a defense reflex?

I mean certainly as a comic there’s that natural urge to let some of the pressure out with humor, so I often tried to find a humorous silver lining when writing this book. But honestly, mostly I just leaned into the dark stuff. I needed to get it out of me urgently so I didn’t really feel any pressure to cut the tragedy with jokes. I wrote this more for me, to heal, to purge, than anything else, so when I was in those dark spaces in the book, I really didn’t force myself to pull out of it. I explored it. Humor comes naturally to me so I wasn’t worried about the book not being funny, I was more focused on making it 100% honest.

How comfortable are you with the silences that happen when you tell a serious story onstage?

When you bomb as much as I do, you have to get very comfortable! I kid, I kid. Professional comic over here! I’ve gotten much more comfortable with silences when discussing serious subjects. That’s what storytelling shows are good for, learning to mine that silence, to not recoil from it, which is a comic’s instinct. I’ve gotten more comfortable. If I’m at a club, though, I earn their trust for twenty minutes first, then I’ll go into more tricky territory.

Tell me about the title of the book. I love the saying from which it springs [“Comedy is tragedy plus time”].

You know, my literary agent came up with that. I was struggling with names and nothing really fit. I was thinking about calling it “Little Sister” but that just didn’t feel right. Then my agent Yishai was like, “How about ‘Tragedy Plus Time?” and I just loved it. I think it’s perfect.

When did you know you wanted to write this book?

When Lydia passed away, I mourned very hard for months. When I was able to pull out of it a little bit, to start to put one foot in front of the other and figure out what the rest of my life was going to look like, I felt like I couldn’t do comedy anymore. And I didn’t want to. I didn’t feel funny. I wrote an essay about what I was going through and put it on my website and it felt like such a relief to just get it out of me and onto the page. And that kind of helped me get back to comedy in a way. Because it was like, “There. I wrote about it. I addressed it. Can I just tell jokes now?” It let me off the hook, so to speak. In my own mind anyway. I think I knew then that I would be writing about this for a long time to come. I don’t know if I knew I was going to write a book then, but I knew I would continue to write about it.

I think that memoirists live many times — once when we experience the events of our lives; again when we write about them; again when anyone else reads that writing and comments on it; and then over and over again every time we re-read, revise, edit, and so on. When I wrote my memoir, I found it really difficult to relive some of the tough stuff. What was the memoir-writing process like for you?

It was tough, obviously. I cried a lot. I really was able to work through some dark shit writing this book. But the real surprise was actually how much I enjoyed exploring my family. It felt like getting to know them all over again. I mean I interviewed my mom and my dad about when they met and what they thought of each other. I had never sat them down and said, “So how did you two meet?” And it was fun to get to know them a little better as people — not mom and dad — but as young badasses courting one another. It was nice to talk to [older sister] Anna about her memories of events. And it was nice to try to bring Lydia to life. That surprised me. I came away more in awe of my family than ever before.

Your family has got to be accustomed to you talking about real-life stuff. Were you worried at all about how they would react to your diving into the story of Lydia’s death?

I was and am. But my family is so strong, and so loving and supportive. The one thing we’ve all tried to do since Lydia died is respect each other’s mourning process. We let each member mourn how they need to. My family understands that this was part of my process and so they respect that.

But I recognize that I chose to do this, I chose to put out my family’s most private grief out for public consumption and I know that’s going to be hard. They’ve all read it, they all like it, but it’s going to be awful when someone comes up to my mom at the grocery store and starts gushing to her about the book. Maybe she didn’t want to talk about the death of her baby that day. I hate that that’s going to happen. But I can’t really control that. I just have to be happy that Lydia gets to come to life for more people. And I know my family is happy that people will get to know what an amazing person she was.

Who are your influences as a writer?

Ken Kesey, Sylvia Plath, Harper Lee, Ernest Hemingway, David Sedaris, Roddy Doyle, Gabriel Garcia Marquez, Flannery O’Connor, John Steinbeck, Dave Eggers, Jack Kerouac, Bukowski, Cormac McCarthy.

Do you want to write more books? If so, what might they be about?

I 100% do. I have a few ideas brewing right now. But a lady never tells.

Are you going to do a reading and signing at Tattered Cover? I know your rockstar Denver presence brought some new readers out when you did the event for Great.

I am. Which is so great. The Tattered Cover is a Denver institution. I grew up in that store. I would pull Calvin and Hobbes collections off the shelves and sit in one of their big comfy chairs and devour them. I’m so honored to get to launch a book from there. It’s kind of making me geek out.

After this book is out in the world, what’s next for you in terms of career plans?

I’m working on adapting the book into a movie. So far it’s been pretty interesting. We’ll see how that goes! Season Three of my TV show Those Who Can’t comes out later this year on truTV. I’d love to get a fourth season and keep making those. We have fun. It’s the smartest dumb show you’ll ever see. I’m proud of it. And stand-up comedy. I’m always out there telling dick jokes to strangers.

Tragedy Plus Time is available now.