For the last half decade, Drake Milligan has proven that success isn’t given, it’s earned.
With two terrific albums under his belt, the Texas native has hit the road hard to support them, earning fans all over the world. With the release of his last album, Tumbleweed, Milligan is offering a revamped stage show that sees he and his band firing on all cylinders. Before year’s end, the “Tumbleweed World Tour” has a handful of domestic dates before Milligan heads to Australia and Europe.
We chatted with Milligan at CMA Fest all about the tour, his success overseas, performing in front of Randy Travis and more!
Pro Country: When we last talked ahead of the “Tumbleweed World Tour,” you mentioned a totally revamped show, with new songs from the Tumbleweed album filling in the gaps in your set. With several dates under your belt, how much have you enjoyed bringing the new songs to the stage and performing a new show?
Drake Milligan: It’s been great. It’s made it feel like a whole new show for me. I’m always trying to evolve the set; we try not to play the same set twice. It’s refreshed me, and the whole band, to revamp the show. It’s made us better.
PC: What has been your favorite song from the album to play on tour?
DM: “Tumbleweed” has been a really nice moment in the show. It’s so different from anything I’ve ever put out. It’s become our “jam” moment in the set.
PC: We saw your recent date in Asbury Park, New Jersey on the tour, where you played covers of two Merle Haggard songs: “Mama Tried” and “I Think I’ll Just Stay Here and Drink.” That said, can you tell us a few of your favorite Merle Haggard songs?
DM: Oh, gosh! I actually listened to “Ramblin’ Fever” coming in this morning. That’s one of my all-time favorite Haggard songs. The second verse, “I want to die along the highway and rot away like some old highline pole” is such great poetry. I love doing “Mama Tried” live; that one is a great singalong. You can’t go wrong with any Haggard song, though.
PC: Tumbleweed landed at number one on the UK’s country album chart, with the single also landing in the top 10, and you have another slew of international tour dates later this year. How encouraging has your consistent success been with international audiences?
DM: It’s incredible. I never expected it. The coolest thing, to me, is that we’ve built it from the ground up. The fanbase in the UK is incredible. They support artists in a way that I haven’t seen anywhere else. They really get behind artists, and they’re proud to be country music fans. They dive into the history of not only my songs, but when they hear me talk about Merle Haggard, they dive into his music too. Country music is happening in a big way over there. It’s not really a niche thing anymore.
Three or four years ago, we decided to dip our toes in over there and go to C2C Festival, and it went over amazing. We’ve been able to build on that, and it’s all coming from the live show.
PC: Most recently at C2C, you were direct support for Brooks & Dunn!
DM: That’s right! There were 17,000 people at the O2 Arena. The best part was finishing my set and then getting to watch a Brooks & Dunn show [laughs].
PC: You recently had the opportunity to record a duet with Shania Twain, “I’ll Be Here With You,” for The Gray House soundtrack. Can you talk about how the song ended up on the soundtrack and what it means to share a song you co-wrote with one of the most iconic country artists of all time?
DM: It was incredible. She brought so much to the song. We started it with Erin Enderlin, Moose Brown and Jeff Fahey for The Gray House. Once Shania came into it, I was pinching myself. Like everybody, I’m a huge Shania fan, and not only that, she’s such a sweet person. With a megastar like that, you never know how they’ll be, but she’s so kind.
Her voice sounds incredible on the song. I was so reminded of how amazing her voice is and the tone in her voice. It’s such a special, impactful song. She brought me up on stage in Calgary to sing it together, too!
PC: Along with the Shania Twain duet, you’ve recorded songs with Vince Gill, Randall King and James Burton. Can you tell us a few bucket list duet partners?
DM: Being a Texas guy, the big ones are Willie and George Strait!
I actually have a cool duet coming up that I just did with Ray Benson of Asleep at the Wheel. He invited me to write with him, and we wrote a song for their new record! It was so cool to get the call from a legend like that. He’d seen a clip of me singing “Goin’ Down Swingin’” and loved it.
PC: Last night, we saw you perform at the 40th Anniversary of Randy Travis’s Storms of Life at The Nashville Palace. How special was it to play with members of Randy’s band and to play in front of the man himself?
DM: I got invited at the last minute, and I was so honored to be a part of it. I couldn’t even tell you how many hours I’ve spent singing along with Randy on the radio. There’s no doubt that my music would be far different without Randy’s influence. Especially for a low-voiced guy like me, Randy is one of the best of all time. I told them they could give me any Randy Travis song, because I can do all of them. Luckily, I got “Storms of Life,” which is a great song off of his debut record that they were celebrating that night.
I waited until the second verse and chorus were done before I even tried to look at Randy. When I finally looked over, he was smiling and giving me a thumbs up. In my head, I thought, “I’m good! I can die now!” [laughs].
PC: You recently played the National Memorial Day Parade in Washington DC, where you had the opportunity to honor lost veterans, talk with veterans and to play with the Air Force Band. How special of a day was it for you to be involved with such a special event?
DM: It was awesome. It was a crazy travel trip for us. Really, it didn’t make sense, logistically, for me. We did our first gig in Monterey, Mexico, and I flew straight from there to DC. I made it to the parade at the last minute. After, I flew back home, packed quickly and flew to Sweden. It was hectic, but it was so important to me to do it. It was a great reminder of why I get to travel the way I do and the liberties we have. You don’t get that everywhere.
I also got to meet some World War II veterans, which was incredible. I got to shake their hands and thank them. It was a really cool experience.
PC: Along with your “Tumbleweed World Tour” dates, what do you have planned for the rest of 2026?
DM: Lots of shows! Later this year, we’re going to Europe and Australia. I’m looking forward to keeping things moving!
I’m always working and writing, too. Hopefully I’ll be back in the studio this summer cutting some new music.
*Feature image by Eric Ryan Anderson*
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