In this interview with Midnight Sky, we explore the inspiration behind “Dark Stretch of Road,” uncovering the song’s emotional roots, its metaphorical weight, and its place within the album Just Before Dawn.
1. Can you take us back to that long night drive that inspired “Dark Stretch of Road”? What was going through your mind, and how did that experience shape the emotions behind the lyrics?
I had been working on a song for over ten years called “Mystery Road,” about a trucker who is killed when his truck runs off the road and is condemned to drive up and down the roads of America for eternity. Despite the content, musically it’s an upbeat rockabilly song. While I was slogging through that one, I thought about a similar theme but much darker (which was consistent with my mood at the time). It took me about an hour to write “Dark Stretch.” And a few days later I finished “Mystery Road.”
2. When you were writing the song, did you see it more as a literal story of being on the road, or as a metaphor for life’s uncertain paths?
The song is definitely metaphorical. I was thinking about how quickly a life can spiral into chaos and hopelessness. Here’s this truck driver leaving St. Paul, Minnesota, which he’s probably done hundreds of times, and suddenly, he’s lost, both geographically and spiritually, and he’s got no map, his phone isn’t working, there aren’t any road signs, and all the buildings are dark. Despite the darkness of the lyrics, it’s been one of my most popular songs. Says something about the human condition!
3. What creative vision guided the making of Just Before Dawn, and how does “Dark Stretch of Road” fit into the larger story of the album?
Much of this is covered above. “Just Before Dawn” suggests, I think, a sense of hopefulness: It’s dark now, but it will be light soon. “Dark Stretch” is saying “don’t be so sure.”
4. How do you balance classic Americana influences with modern storytelling and production to create a sound that feels both timeless and current?
I didn’t know I was doing that until you mentioned it! But seriously, I have a great co-producer, Chad Burton. When I’m writing songs like “Dark Stretch,” I consider whether this sounds like a song that could have been written 100 years ago. I struggled with the mention of a cell phone in “Dark Stretch,” because it corrupted the timelessness of the song. Ultimately, though, I didn’t want a critic to say: Why didn’t he just call somebody?
5. The song speaks to perseverance and faith through uncertain times. In what ways do you think “Dark Stretch of Road” reflects where you and your listeners are in today’s world?
We are in a very pessimistic place right now as a society. But I think I wrote “Dark Stretch” in the mid aughts, so maybe things haven’t changed as much as they seem. What matters, I think, is that the album is balanced by some very optimistic, upbeat pieces. What I didn’t want to create was a 50-minute dirge.
6. With “A Few Good Years (Remix)” reaching Billboard’s Top 50 and earning critical praise, how has that success influenced your approach to songwriting and connecting with audiences going forward?
Not at all. I’m thrilled that “A Few Good Years” has done well, but I’m not going to concentrate on that style of song just because one did well. I could write ten more songs about what’s really important in life and the virtues of optimism, and they could all be stinkers. Like most songwriters, I think, I write the best song I can, and then I roll the dice.
Copyright © 2025 The Inteviewist
