Drake Milligan on Capturing a Fresh, Nostalgic Country Sound on New Album, ‘Tumbleweed’

If there’s an artist that can claim they’ve lived the lyrics of Hank Snow’s “I’ve Been Everywhere,” it’s Drake Milligan. One look at his tour schedule over the last few years feels like he’s been around the world and back at least once, building a reputation as one of country music’s top live acts along the way.

Milligan isn’t just hitting the road to see the sights, though. Since the release of his debut album, Dallas/Fort Worth, in 2022, Milligan has used the road as a vehicle to hone his vocal chops. Hundreds of shows came and went before his sophomore effort, Tumbleweed, a project that sees the Texas native with a full grasp of his artistry and what he wants to say.

Some of the songs on Tumbleweed, like the infectious “Slow Dancing to a Fast Song” and rowdy “How Much Beer” have been live staples for years, while others are set to make their debut on a world tour in support of the album, where Milligan is promising a revamped show.

We chatted with Milligan all about Tumbleweed, as well as growth, the neo-traditional country resurgence, the “Tumbleweed World Tour” and more!

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Pro Country: You released your last EP, Jukebox Songs, about a year and a half ago. In the time since, the EP has earned millions of streams across platforms, and was the first time you’d recorded outside songs. With that time having passed since its release, how do you look back on the project and what it did for you as an artist?

Drake Milligan: That EP was a great stepping stone between my first record and my new record. That EP made me a lot more confident in my song choice ability, because of the response I got from it. It affirmed that I can be a voice for songwriters in Nashville. I grew up with artists like George Strait, who cut mostly outside songs, but he had a way of making them his own. It’s cool when the songwriting community in Nashville gets behind you when you do that, too.

That EP was a great stepping stone, too, with working with Trent Willmon. That was our first time working together, and we established a great working relationship, so we were very comfortable going in and working on this record.

PC: “Tumbleweed” was the first song released from your forthcoming album of the same name, and was written by Bobby Pinson, Cam Newby and Ian Christian. Can you talk about how you heard the song and what you loved about it?

DM: Trent Willmon had gotten ahold of it and sent it to me. I was immediately struck with the melody; it just stuck with me. Every now and then, you hear a song and know exactly what to do with it. I knew how to make it my own. Production-wise, I knew where I wanted to go, and I knew how I wanted to sing it. And I was lucky to record it with some of the greatest musicians in Nashville to help me pull that off.

It stuck out to me lyrically, too. In a lot of ways, I feel like a tumbleweed. I’ve played a lot of shows over the last three years; probably over 300. You can feel tossed around like a tumbleweed sometimes, but I have a great support system around me: my fans, my family and my team are like the wind: the reason behind it. To me, that subconsciously hit me when I heard the song and helped me put a piece of myself in it.

PC: You’ve mentioned Trent Willmon a few times. As you did on Jukebox Songs, you worked with Trent on Tumbleweed. How much have you enjoyed working and collaborating with someone so respected in the industry, and what kind of camaraderie do you feel with him in the studio on your second go-round?

DM: Trent is a fellow Texan, through and through, so I really appreciate that. I first met him years ago in a writing room. It’s been great to work with him. He’s an easy-going guy and the nicest dude you’ll ever meet. He’s put a lot of trust in me as an artist. He trusts what I’m hearing and is able to capture that. He’s a great guy to have standing behind me, but he’s also great at bringing in ideas. I love Trent’s singing, so I even got him to sing a little bit on the record. It was fun to work on the record with him.

PC: The last time we talked, you mentioned that some of the vocals on the Dallas/Fort Worthalbum were as old as 2019. As you were gearing up to record a new album, how much were you looking forward to showing your growth as an artist on a full-length project?

DM: It’s funny, when I listen back to the Dallas/Fort Worth record, I was still a baby [laughs]. I’ve grown a lot as I’ve played a lot more shows and have been singing a lot more. I have a better understanding this time around of both myself as an artist and my audience. I’ve written a lot more songs and spent a lot more time in the studio since then, too. Because of that, it was a lot quicker to make this record. You’ll hear some live vocals on this record, which I think captures a lot of the energy of a live feel; something you don’t really feel if you’re splicing up vocals weeks later. You lose some of that magic. 

PC: We’ve seen you perform “Slow Dancing to a Fast Song” as early as June of 2023. What was it that kept the song in your head and made you believe Tumbleweed was the right project to feature it?

DM: That song has always hung around. Every time we went in to record; even when we did the EP, I would say, “hey, what about ‘Slow Dancing to a Fast Song’?” and everyone thought I’d already recorded it. It’s such a fun live song, and it’s even more special now to put it on a record, because people have been to my shows and have been anticipating it. Now they can say, “yes! Finally, it’s out!”

I wrote that song seven years ago, and have been playing it since I had a live band. It’s evolved a lot on the road, so we got to take that into the studio.

PC: “Hard Headed Cowboy” is one of our favorite songs on Tumbleweed, and is a song you co-wrote with Aaron Eshuis and Neil Medley. Can you take us in the room and talk about how the song and story came together?

DM: It started in my living room, maybe two years ago now. I was sitting here listening to Marty Robbins records, and I might’ve had a couple too many whiskey drinks that night [laughs]. I’ve always been such a fan of Marty Robbins’ singing, but I think a lot of people forget how prolific he was as a songwriter. He wrote so many amazing cowboy ballads, and you could picture them immediately. The imagery is so simple and concise, and it’s so hard to write a song where you can see the whole story happening, especially on songs like “Big Iron” or “El Paso.”

I was listening to the Gunfighter Ballads and Trail Songs record, walking around and singing “El Paso” like Marty Robbins. I sat down with a guitar and thought it would be cool to try to write something like that.

I came up with a chord progression that eventually turned into [singing] “the day that the hard headed cowboy rode out of town.” I thought there could be a whole story about that. I feel like I’ve created a character within my catalog about a ramblin’ guy who’s thinking about setting down, but he’s not ready yet. Even going back to “Sounds Like Something I’d Do.”

I stayed up all night working on the song. The next day, I was writing with Neil and Aaron. I almost called Neil in the middle of the night and said “dude, this is it!” Somehow, I’d convinced myself that it was the song that was going to break my career [laughs]. Of course, I woke up the next morning and thought “what the heck?!”

I think they were a little wide-eyed when I brought it in, but they were great collaborators on the song. They helped bring my vision to it and brought the simplistic imagery and storyline that Marty was able to do. It’s a bold song to put out, because there’s not a lot of songs like it.

PC: One of our favorite songs on Dallas/Fort Worth was the fantastic swing song, “Goin’ Down Swingin’,” and a favorite on Tumbleweed is “Talk Texas.” How much do you enjoy tapping into the swing sound and paying homage to that influence?

DM: I love it. The more I get into music and the more I’m on the road, the more I’ve gotten my band to love playing that stuff. I feel that sound is an important thing to keep alive. I love the music of Bob Wills and Asleep at the Wheel so much. There’s been some torch carriers, but it’s something that I don’t see a lot of in today’s country music. We play “Goin’ Down Swingin’” everywhere we go across the world, and even if people don’t know western swing music, it’s so infectious; it invites players to be great players and the audience to participate and have fun. For me, songs like that and “Talkin’ Texas” are me trying to be a torch bearer for that music.

There’s a lot of great, up-and-coming artists that are doing it. Jake Worthington has that influence and is great at doing it. I feel like the revitalization of it is coming. I’m seeing it with my friends who grew up on the same stuff, and it’s really cool to see.

PC: To that point of sounds coming back, Tumbleweed comes at a time where there’s a big neo-traditional resurgence in country music happening with artists like yourself, Jake Worthington, Braxton Keith and Zach Top having a lot of success. What has it been like to see that sound coming back around and seeing more and more fans connecting with it?

DM: It’s what I dreamed of. When I moved to Nashville about seven years ago, it was starting to happen, but we didn’t really have an artist like Zach blow up, which has been awesome to see. There’s plenty of artists out there who are great singers, writers and players that don’t get the recognition they deserve, so it’s great to see a guy who’s a great singer, writer and player getting the recognition he deserves. And the music he’s making is unapologetically country. It opens the door for guys like me to do our thing in our own unique ways. The great thing about country music in the 90s is that there were so many artists who were traditional that had their own lanes: artists like George Strait, Alan Jackson, Clint Black and Travis Tritt. They had their own influences and were so unique in their own ways, and I think that’s what you’re seeing right now. I look around at a lot of my friends, and nobody is copying each other. It feels like a great time to have a revitalization of that stuff, because there’s a lot of great, young artists out there

PC: Tumbleweed closes with a rowdy duet with Randall King, “How Much Beer.” Can you talk about how Randall came to be involved on the song and how much fun it was to record the song?

DM: That’s a song I wrote years ago with Luke Laird and Brice Long. We’ve been playing it live for the last couple years, and it’s been working out. When it came time to record it, I got to thinking that it would be fun to bring one of my buddies in on it. Randall was the first guy I thought of. I love what he’s doing; he loves honky tonk music, and he’s put out consistently great music for many years. I texted him the song and asked him if he had any interest in singing it with me, and right away, he said, “oh yeah!” [laughs]. It was super fun, and hopefully, it gives us a chance to go out and play shows together.

PC: What do you hope listeners take away from Tumbleweed after listening all the way through?

DM: This record is different from Dallas/Fort Worth. I feel that the sound hasn’t changed much, but it’s been many years since I wrote a lot of those songs, and recorded many of them. I feel like there’s more maturity in the writing and song choices on this record. There’s different flavors of country music, too. I hope people realize the sincerity and commitment that I have to country music through this record. All I’ve ever wanted to do is make music that feels nostalgic and classic, but at the same time, feels new. There’s so many songs on this album that do that. This album brings back so many of the sounds and story songs that I love in a way that feels fresh. I feel that Trent and I did a great job of that on this record. I hope people see that I’m trying to do this for a long time, and I think making a record like this is how you do it. There’s a lot of meat on the bone. I’m excited!

PC: You recently announced the first leg of the “Tumbleweed World Tour” with domestic and international dates already on the books. How much are you looking forward to hitting the road hard to promote Tumbleweed and being able to perform songs from the album?

DM: I’m really looking forward to it. We’ve got a totally revamped show. As a performer, I try to remember that each show is a brand new show that a lot of people haven’t seen. Even though I’ve done it hundreds of times, I try to bring that energy every night. Having these new songs in there is really going to help me as a performer, on top of all of the magical moments we’ve had over the years with many of the older songs. It keeps it new for me and the band. We’re going to be finding great little things about these new songs that we can do live. It gives me a whole new excitement to go on the road and make the show even better. Choosing songs for this record was partially about filling gaps in the show. We kick it off on November 11^th in Nashville. It’s going to be a special night. A lot of the people that worked on the record are going to be there, and we’re going to be debuting a lot of these songs. I’m really excited for it!

PC: You’ve had fantastic success internationally over the last few years, with “I Got a Problem” topping the charts in Australia, your duet with The Reklaws, “Honky Tonkin’ About,” topped the charts in Canada and you’ve regularly packed international venues. How much have you enjoyed the success and support that you’ve so consistently seen from international fans?

DM: It’s really cool! I never dreamed that would happen. Growing up in Texas, you don’t really think that you’ll go to Europe and play country music for people. There’s a huge fanbase there for it. It’s a very new fanbase, and it’s exciting to everyone there, and to us as artists. Everybody is so kind to us. It’s been wild to see my music taking off there and that we’re packing venues. They appreciate the traditionalism of country music the same way I do. I can go out there and play a Buck Owens, Roy Orbison or Elvis song, and they’ll go wild for it. It gives me a lot of faith in country music as a whole.

*Images by Eric Ryan Anderson*