Glory Days

Tyler Watamanuk talks to humorist Simon Rich about his latest book and being an accidental anthropologist of millennial life.

Simon Rich’s first book, Ant Farm, was published in April 2007, while Rich was still a senior in college. “Some of the pieces in that book date back to high school. I think the earliest one in that book is ‘Math Problems,’ which was about a teacher with depression,” recalls the writer. Since then, Rich’s career has taken him from writing gigs at institutions like Saturday Night Live and Pixar to show-running the television series Man Seeking Woman and Miracle Workers. Along the way, he’s written an armful of witty books, including his latest collection of short stories, Glory Days.

Rich often writes about his recent past. “The stories are all connected to literal events in my life, but they tend to be delayed a few years,” he says. He’s drawn to the things that “loom large” in his mind after they happen. Sometimes, they’re big emotional moments and significant life milestones; other times, they’re the little curiosities and quiet indignities of everyday life. He always manages to excavate the emotional truth from his out-there concepts—whether that’s the story of a self-conscious Brooklynite visited by his time-traveling ancestor, a recently laid-off grasshopper with a graduate degree looking for cocaine at a wedding, or a supervillain named Death Skull, who finds making friends after forty to be near impossible.

Over the last 17 years, Rich’s stories have touched on everything from post-college malaise and unstable employment to seeking true love in your twenties to parenting in an era with easy access to edibles. His characters struggle with a world that isn’t as easy as the one they were promised. They settle for jobs as “content specialists” instead of becoming the artists or musicians they hoped to be. The stories are peppered with millennial-gen references to Four Loko, Kickstarter campaigns, artisanal pickles, American Apparel and student loan debt. Still, Rich balances out his sharp tongue with his warm heart, always offering enough hope to not send his reader into a total downward spiral.

Dirt spoke with Rich about writing through the significant milestones of his life, the millennial archetype, and why he hates writing in his own voice.

Tyler Watamanuk: Glory Days is very much a "mid-life" book, but I wanted to start with your first book, Ant Farm. What was your life like at the time you wrote it? What did you hope your life and career would look like?

Simon Rich: That book was released right before I finished college. I wrote most of it in college, but some of the pieces in that book date back to high school. More than anything, I wanted to be allowed to write fiction for a living. That was my dream. I didn't have any higher ambitions than that, and I was so excited when that book resonated with people because I knew it meant that I got to write some more.

I was writing for a number of magazines back then, many of which no longer exist. It was the last gasp of print media as a growth industry. I remember writing one short story for a magazine called Best Life, which was, I believe, a spinoff of Men's Health. I was writing for Mad Magazine. I was writing for the New Yorker, which I still write for. I also used to write short pieces for the radio. It sounds like I'm describing the career of somebody who lived a hundred years ago, but that's what the state of media was. Pre- 2008 recession, there were still these glossy magazines that you could write for. I was kind of living the freelance comedy fiction writing lifestyle, and then I started writing for Saturday Night Live.

TW: What did your life look and feel like when you started working on the stories that would become Glory Days?

SR: It's very much a turning 40 book. I think for a lot of people in midlife, 40 is an age that forces you to take stock of where you are. You're halfway through your existence. It's impossible not to pause and consider or reconsider your priorities and values. So it's a book filled with characters who are in midlife and kind of reexamining the choices that they've made, and, in many ways, redefining what it means to win. 🏆

DIRT Q&As, LATELY

MILLENNIAL CRINGE