How Preston Cooper Went From ‘The Singing Mailman’ to Writing His First Country Hit With The Warren Brothers

Singer, songwriter and guitarist Preston Cooper may be celebrating a series of career firsts in 2025, including his initial entry on Billboard’s Country Airplay chart with his debut radio single, “Weak.” Yet his raw, blues-dipped sound and commanding voice were forged through years of regular gigs around his home state of Ohio.

“Everybody’s like, ‘Oh, you’re an overnight star,’ but no, it’s taken about eight years,” Cooper tells Billboard.

Building upon previously released songs including “Weak,” “Numbers on a Mailbox” and “Used To” (which Cooper also plays guitar on), he includes those songs on his upcoming release Toledo Talkin’, his debut full-length album, out on Aug. 29 on Big Machine Label Group.

Growing up on a cattle farm in the small town of Fredericktown, Ohio — an hour northeast of Columbus — Cooper sang in the school choir as a freshman, but it wasn’t until he saw a classmate play in guitar class that he discovered his true passion. “He was up in the corner of the room playing, and I could tell he was actually good,” Cooper says. “He showed me some chords. I loved the guitar, and then I started putting some words to the [melodies] and singing with it. We ended up playing in some bands together.”

Cooper started off with rock classics such as Metallica’s “Enter Sandman,” The White Stripes’ “Seven Nation Army” and Deep Purple’s “Smoke on the Water,” quickly adding to his repertoire hits by Chris Stapleton and John Mayer. After graduating high school, he became a mailman, walking up to 14 miles a day. To pass the time and entertain residents along his route, he sang snippets of songs and made up melodies, quickly earning the nickname “The Singing Mailman.” Off the clock, he regularly played in local bars and restaurants, eventually making more money from shows than his mail route.

“I didn’t play bro country, but like, Stevie Ray Vaughan, lots of [Chris] Stapleton, Bill Withers, B.B. King. I kind of played whatever I wanted to play,” he recalls of those gigs. 

While playing a fundraiser in Toledo in 2023, Cooper and his music caught the attention of Nashville songwriters Brad and Brett Warren, also known as The Warren Brothers, who have written songs for Toby Keith (“Red Solo Cup”), Tim McGraw (“Highway Don’t Care”) and Martina McBride (“Anyway”), and who overheard Cooper performing during their meet-and-greet. 

“They were supposed to be meeting people, but they kept coming in and watching me play,” Cooper recalls. Three weeks later, he made the trip to Nashville to write with the Warren Brothers and perform at Nashville’s The Bluebird Cafe. 

“They were just throwing me into the ballgame, and it was cool,” Cooper says of first coming to Nashville. That first writing session turned into his debut radio single “Weak,” and evolved into Cooper signing a publishing deal in 2024 with The Warren Brothers and Warner Chappell Music Nashville, followed by a label deal with Big Machine Label Group.

By the time he signed with Big Machine, Cooper had already been working on Toledo Talkin’, balancing songwriting and recording sessions with those bar gigs back in Ohio. “I was still doing that to make money to live [in Nashville],” he says. “It was really hard.”

The new album finds Cooper highlighting his range of influences. He delivers a Stapleton-esque, raspy-soul vocal on “The Takedown,” a tale about finding the courage to leave the comforts of home in favor of the unknown. He proves he can handle full-throttle country-rock with aplomb on “One For The Road.” The album’s closing song finds him etching a tale of a down-on-his-luck musician on the street doing his own kind of spiritual preaching. “He’s singing the gospel truth/ It’s coming out like the blues,” Cooper sings.

Cooper’s music, soulful vocals and bluesy guitar-playing had Nashville industry execs talking during Nashville’s Country Radio Seminar in February, and he’s opening shows this year for Kameron Marlowe and Riley Green. Cooper, Billboard’s August Country Rookie of the Month, recently discussed the making of his debut album, working with The Warren Brothers and his dream collaborations.

How did the song “Weak” come about?

Three weeks after I met The Warren Brothers, I went to Nashville to write with them and Lance Miller. I pulled out that “Weak” melody, which I made up on my mail route, and they were like, “What?!,” and helped me put lyrics to it. We wrote that song in like 45 minutes, and then recorded it immediately.

What songwriting lessons have you learned through writing with them?

They are some of the best. They taught me little tricks, things like double meanings in songs. They are the masters of that. They’ll write something that has three meanings in one line.

Another standout on the upcoming album is “If This Table Could Talk,” which you also wrote with Brad and Brett Warren. What was writing that like?

That was [written] quite a while ago, like November 2023. It’s probably one of my favorites. Lyrically, it’s just a great song, and it ties into my life a lot — just growing up, things that table’s seen, happiness, sadness, divorce, marriage, all that stuff. I showed some friends that song and it speaks to them.

“Numbers on a Mailbox” links to your days as a mailman, but it’s one of very few songs on the album that you did not write. How did you hear it?

[The Warren Brothers] wrote that about eight years before I met them. It was like this God moment of “That’s just a perfect song for you.” I’m from a small town, and I worked at the post office—there was no other better person to cut it than me.

How did you come to Big Machine’s attention?

Brad Warren texted [Big Machine Label Group executive vp of A&R] Allison Jones and was like, “Hey, I haven’t asked for a favor in a long time, but I would like you to meet this kid we found.” Allison called [Big Machine founder/CEO] Scott Borchetta, and we had a meeting at Big Machine. I played him three songs, and he was like, “That’s enough.” That kind made my heart stop. But then he was like, “When do we start?” I was meeting with other [labels] at the time, and it felt like here I could musically kind of go where I wanted to and they would support it.

Who would you want to collaborate with?

In the country world, Chris Stapleton is my hero. I’d love to do something with him. And Bob Seger, the Foo Fighters, and, of course, John Mayer.

What is one album you could you listen to over and over?

Probably the Escape album by Journey. 

When you are not doing music, how do you spend your time?

I love to deer hunt and turkey hunting is probably my favorite, but I love to coyote hunt, too.

It seems that most artists have to contend with the constant need to feed the social media machine. How do you approach that? 

I’m trying to get better at it. I don’t mind it, but I didn’t grow up on social media. I was always out in the woods, and I just didn’t think about pulling out my phone and showing people what I had for breakfast, right? I love the reach [of social media], though. That’s how people find new music.

 What are a few things on your career bucket list?

[Playing] Red Rocks, and that will happen in a couple of weeks [with Green], which is wild. I’d love to play Madison Square Garden and the Ryman [Auditorium]. I’ve never even been there. I’d love to play there.