A warm, medium-shot portrait of country singer Drake Milligan, captured in a classic, neotraditional aesthetic. He is seated in the driver's side of a white pickup truck with the door open, looking directly at the camera with a subtle, confident expression. Drake is wearing a dark brown suede Western-style jacket with decorative scalloped stitching across the chest, layered over an olive green vest and a cream-colored knit polo shirt. His dark, wavy hair is styled in a relaxed, swept-back look. The lighting is soft and golden, suggesting a late afternoon or "golden hour" setting, which complements the earth tones of his outfit and the vintage feel of the truck.
Drake Milligan Credit: Eric Ryan Anderson

Years before Austin Butler stole the hearts of music biopic lovers everywhere, 27-year-old country singer-songwriter Drake Milligan—then barely out of high school—portrayed Elvis Presley on CMT’s “Sun Records.”

Now that he’s seasoned with experience on “America’s Got Talent,” and has penned enough country music material to open for the likes of Luke Bryan and Lainey Wilson (the latter of whom he made his Tampa debut opening for less than half a year ago), Milligan is taking his new, sophomore studio album Tumbleweed on the road for a proper run of gigs.

Ahead of his stop in Sarasota this weekend, Milligan told Creative Loafing Tampa Bay about the album that changed everything for him. Read his full quote below.

It’s a tough question, but the album that really comes to mind first is Alan Jackson’s Under The Influence from ’99. I can remember growing up with that record, and I remember sitting there as a kid, just being obsessed with it — holding it, looking at the cover. It’s interesting, because Alan Jackson is one of the best songwriters in country music ever, but it’s a covers record. It’s all covers, and really, that record introduced me to so many different songwriters and artists. There’s a Merle Haggard song on there, there’s a Charley Pride song, there’s a Bob McDill song. And he made those songs just his own. Songs like “Pop A Top” on there, which was kind of a modern hit, was from Jim Ed Brown back in the day. Alan was able to take it and make it his own.

I’ve just always been obsessed with that record, and even now, during my own career, I kinda go back to that record because I think that’s proof of a great artist, because being able to take songs, as somebody like Alan, who I’m sure reveres this music so much, but also make them fresh in a way. That record still comes to mind — it’s been a part of my whole life. It introduced me to so much music, and it’s just a good country music record. I think it’s a good starting point for anybody, really. It’s so palatable to get all those songs, and you can kinda branch off and listen to all these different, original versions of the songs if you want to, and see how much they’ve changed. —Drake Milligan

Tickets to see Drake Milligan play Sarasota’s Joyland Live on Saturday, March 28 are still available and start at $26.23.

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Josh Bradley is Creative Loafing Tampa's resident live music freak. He started freelancing with the paper in 2020 at the age of 18, and has since covered, announced, and previewed numerous live shows in...