Interview: Trapper Schoepp (with Leroy, the Boston Terrier)

“Hello, you’ve reached the office of Leroy, the Boston Terrier – his representative Trapper Schoepp speaking.” This is the way Schoepp answers the phone, amused, for a recent conversation about “I Am a Rider,” the latest single from his acclaimed album May Day (released in 2021 via Grand Phony Records). For just over a decade now, the Milwaukee-based singer-songwriter has steadily been building a reputation for being one of the finer young songwriters, deftly mixing rock, folk, and Americana, often with a dash of humor. He is also, as he proves with “I Am a Rider,” an expert at directing eye-catching videos to match his memorable music. For this one, Schoepp tours fascinating spots around his hometown on a bike, with the scene-stealing Leroy along for the ride. See below for a link to watch it). And, Schoepp promises, there is even more new music already in the works.

What inspired you to write “I Am a Rider”?

TRAPPER SCHOEPP: I was listening to NPR, and I was hearing a pilot talk about how he became comfortable flying a plane. And he said, “How I get in that mindset is just thinking, ‘Aviate, navigate, communicate.’” And those are the first three words of the song. I think the song is inspired by life on the road, as well as the age of anxiety that we live in. I thought biking around with a dog [for the video] is a nice way to offset the darker themes in the song. Mixing those two things, darkness and light, is the classic combination.

No offense to you, but I think Leroy is going to emerge as the real star of your “I Am a Rider” video!

TRAPPER SCHOEPP: Of course. As it should be.

How did he come to co-star with you in it?

I have had Boston Terrier dogs for the last ten years or so, and I found out that the best way to wear a Boston Terrier out is by putting them on a leash beside me on a bike late at night down by Lake Michigan. But I thought, what if I can actually put a Boston Terrier on the bike. Make him look like a little superhero. Two of my Bostons would not tolerate it, but young Leroy is a puppy, a year old, and he absolutely is into riding around on this bike with me. And the song is called “I Am a Rider,” so what better way to present the song than with a dog video.

It’s basically a love letter to Milwaukee, where you’ve lived for many years. Why did you decide to showcase it like this?

TRAPPER SCHOEPP: I think Milwaukee is a criminally underrated city. Its art, music, dining and sports scene have really begun to blow up in the last few years. And I think it’s just such a scenic city, right here on Lake Michigan. And I think, too, this city has such terrific music venues. We just played The Pabst Theater with The Wallflowers, and that venue is among the best I’ve played in the entire world – state-of-the-art acoustics, and the accommodations and flow of the venue rivals the world’s best. So I think the city has a lot to offer. There’s so much vibrancy and energy happening [there] right now. It’s a great time to call myself a Milwaukeean.

How did you decide which places to include?

TRAPPER SCHOEPP: Truthfully, a lot of these spots are just places I go every day in Milwaukee. It’s a very small city, accessible, and so we were able to film all of this in a day. The film producer, Samer Ghani, followed me around in his Jeep. We went around and filmed the magic. At the Milwaukee Art Museum, there is a bridge there that connects the art museum to the city, and there were tons of people taking selfies. Meanwhile, I was biking with a dog across it. My brother was behind me on a unicycle. It was just a comedy of errors to try to make some of these shots work, to say the least.

Between this video and the animated one for your song “Yellow Moon,” you seem to be on a streak of making very memorable videos…

TRAPPER SCHOEPP: I have a really good time developing music videos. I think that comes from my youth. I used to make BMX bike videos, some more ridiculous than others, when I was a kid. This is just a continuation of that. I think we are living in the age of multimedia, and tools to make films have become so much more accessible in the modern age. And I just enjoy it. I’m not setting out to make crazy viral sensations. I’m just looking to bring my songs to life, in a way that feels authentic to me and is cost-efficient.

What do you have coming up next?

TRAPPER SCHOEPP: We just recorded an album called Siren Songs at Johnny Cash’s cabin in Tennessee, and that album is more of a traditional folk approach. That is my roots; I grew up loving and listening to a lot of folk music. We will be [playing shows] on the East Coast in the spring of 2023 for that new album.