Andrew Careaga

Friday Five: ‘Denali, Alaska’ author Tyler Dempsey

‘Each essay is a tiny vessel exploring the mosaic of my experience…’

Don’t let the title of Tyler Dempsey’s latest book, Denali, Alaska, fool you. That may sound like the name of a travelogue or guidebook, but this collection of essays, now out from Trident, is as expansive as the state he called home for more than a decade.

A black and white image of a man sitting on a couch with two dogs, one on his lap and another behind him, looking relaxed in a cozy indoor setting. On the right side, there is a book cover titled 'Denali, Alaska' by Tyler Dempsey, featuring a scenic mountain landscape. — Left, Tyler Dempsey with his two dogs (husky Ally and Labrador mix Wilt). Right, the cover of his new essay collection, *Denali, Alaska*, now available from Trident.

Yes, there are plenty of first-person accounts of Tyler’s adventures in the wilds of The Last Frontier, including a stint as a backpacking guide for a Belgian film crew to the site of a famously doomed American adventurer (the subject of the book’s penultimate essay). But each of these essays, like the author himself, covers a lot of territory, from life in Alaska (“the size of two Texases,” Tyler reminds us) to banana farms in Hawaii, hitchhiking in Montana, leaving his native Oklahoma, and hanging out in the Bay Area of California, “trimming friends’ marijuana for supplemental income.” From these and other geographical jumping-off points, Tyler takes us on a journey about family, love, sex, physics, Native American rock writings, ultramarathoning into the hottest places of the U.S., close encounters with bears, and many and sundry internet rabbit holes that have piqued his curiosity over the years.

What makes each of these fifteen essays so interesting and enjoyable is the way Tyler deftly connects seemingly unrelated ideas and weave them into a cohesive fabric. His nonlinear, hopscotch lateral thinking style shines through in every essay. As he writes in “Stop Making Sense,” he is “plagued by ideas.” His mind is like “a drunk toddler grabbing flash cards. … Though I may not understand it when I begin, something is connecting the disparate strands.”

The result, as he puts it in the interview below, is a set of essays, each of which “is a tiny vessel exploring the mosaic of my experience, sticking to one thing for a few seconds before moving away to see what jumps up from the goo next.”

An adventurous soul who has endured some of the most extreme climates and conditions in North America, Tyler is also the product of a single-parent household and some of the common and not-so-common realities such a life brings, and he and his wife are new parents. He’s also Blake Shelton’s stepbrother, a tidbit some writers (like myself) might latch on to as fodder for an essay all its own. But that factoid barely merits a mention in Denali, Alaska. Tyler simply has too many other interesting things to say.

Denali, Alaska is Tyler’s fifth book and first essay collection. Many of the pieces were previously published in popular alt-lit magazines over the past few years. You can find all his books on his website, as well as some of his essays and other writings. Until this year, he also hosted a podcast called “Another Fucking Writing Podcast” (archived on his website) and for six years published an annual roundup of his favorite short stories.

Tyler now lives in a small town in Northern Arizona with his family.

Read on to learn more about Denali, Alaska, why Tyler stepped away from his podcast, why he prefers to write nonfiction, and more.

Saturday Six: get your creep on

Some scary tales to keep you up at night

No Friday Five this week. Instead, and in honor of spooky season, here are six short and scary reads for Halloween.

1. “Vampires,” by Sarah Wolfe

A part of you relaxes. Ignore that whisper in your ear: you will bleed. Intrusive thoughts—a ride you didn’t buy a ticket for.

A macabre micro via Gotham Literature.

2. “Dolly Builds her Brother out of Butter in the Room her Mother Grew,” by T.J. Burgoyne

Butter does for flesh, but not bone. For that, she cuts hardwood from fallen oak, takes Father’s knives to carve ulna and radius, tibia and femur, scoops out hip sockets with the hook-blade and slots the bones together at tallow-greased joints. She scavenges the rest: the spine of a stag found rotting under stooped willows; the finger-bones of a thief; her mother’s skull, plucked from the pyre in the grazing field after Father was sure there was no flesh left to burn.

This story took second place in Fractured Lit‘s 2026 “Ghosts, Fables & Fairy Tales” competition.

3. “Gator Empire,” by Nadine Rodriguez

“Kelsey,” Angie calls out from the shore, and slowly, Kelsey turns to swim to her. When she’s near, she peeks her head out of the water, red hair flattened atop her skull. Angie stares as Kelsey’s clear, third eyelid blinks away to reveal moldy, amber eyes staring back at her through reptilian slits.

Good stuff from Be About It Press.

4.. “The Lantern,” by Jennifer Ostopovich

I felt as though a strange fever had overtaken me. I shivered, at once hot and cold, and drew the lantern nearer to my chest as though the small flame might warm me. Another wail resounded through the forest sending a tremor through me.

The man must have sensed my distress because he asked, “Is something the matter?”

“It’s the Bean Sídhe. It wishes to cross the threshold, to bathe me in the darkness. I must get to the sacred bonfire before my flame goes out.”

One of Apocalypse Confidential‘s featured Twelve Nights of Halloween stories.

5. “Fitting In,” by Verity Mason

Every October, the literary magazine Spillwords publishes haunting stories for its “13 Days of Halloween” feature. This one’s a story you might call gripping.

I kicked out frantically as another tendril wrapped around my ankle. Then another. They climbed my calf, sliding beneath my trousers. I grabbed hold of one and pulled. It was warm.

6. “Candy Bars With Razor Blades Inside Ranked By Johnson Street Address“

A throwback literary listicle, more humorous than horrific, from The Gorko Gazette.

There is no name on the mailbox, but I heard this guy takes big black trash bags out the back after midnight and once a lady that Jesse knows went into his house and never came out. He always leaves a bowl of M&Ms on a chair outside his front door that are gone in about 5 seconds and might as well be mustard gas for all we care.

Cover image via Pexels.

My nine books …

… and why I think they matter

If you travel in writing circles on social media, you’ve probably seen the “nine books that shaped me” meme that has been circulating in recent weeks. On the website myninebooks.com, you can enter the names of your nine favorite literary works (or any other book) and it will pull up a cover image of each of the books, arrange them in a three-by-three grid, and allow you to save and download the image if you wish, or share a link to your grid on your favorite social platform. (Make your own book grid.)

I put together my list from memory in a few minutes, and if I had it to do over again I might remove one to make room for The Grapes of Wrath, but it would be tough to decide which to cut. Anyway, here’s my grid and, because I can’t just blithely post a grid without presenting an argument for why I think these books merit my attention, below the image is my summary of why these books matter to me.

A grid featuring book covers of nine selected titles, including 'One Hundred Years of Solitude', 'Geronimo Rex', 'The Complete Stories', 'The Things They Carried', 'Invisible Man', 'The Brothers Karamazov', 'The Illustrated Man', 'A Confederacy of Dunces', and 'Catch-22: 50th Anniversary Edition'.

Something I’ve been itching to tell you

My responses to 10 questions from The Itch Lit

Last week, The Itch Lit published a 10-question interview with me about memory, inherited beliefs, storytelling, and what I’ve learned from writing nonfiction, among other things. You can read it here.

The Itch Lit is relatively new to the online literary scene. On its about page, the editors describe it as “an online literary magazine devoted to the stories, poems, and essays that won’t leave us alone. We believe the best writing follows readers home, tugs at their sleeves, and demands another look.”

I’m grateful to The Itch Lit for publishing my creative nonfiction piece “Killing Machine” last June. This up-and-coming magazine is publishing some captivating writing. Check it out.

Paying homage to the ‘old daddy of rebel writing’

Remembering Missouri writer Jack Conroy, instigator of the proletarian writer movement of the Great Depression

Who could imagine, in these times, that my beloved deep-red home state of Missouri once harbored one of the leaders of a radical, left-wing literary movement that gave rise to some of the late twentieth century’s most acclaimed writers?

A man sitting in a chair, reading a paper, with a thoughtful expression, in a room with a window showing a cityscape. — “Jack Conroy in Repose,” photograph by Wayne Barker, Works Progress Administration Photographer – https://collections.newberry.org/asset-management/2KXJ8ZS9NT6VZ, Public Domain, https://commons.wikimedia.org/w/index.php?curid=157761215

In the heart of Little Dixie, a self-taught writer’s words took him from the rubble and rabble of Monkey Nest, a coal mining village just outside my hometown of Moberly, Missouri, to literary fame during the Great Depression. Jack Conroy‘s novel about the working class, called The Disinherited, took him to the pinnacle, but too quickly he fell into neglected writer status. Too independent for Communist Party orthodoxy, Conroy butted heads with what he called the “New York intelligentsia,” and eventually his brand of Heartland socialism fell out of favor. I hope my recent essay about Conroy will help raise awareness of his crucial role in creating an important literary movement in America.