When Simon Cowell turned his nose up at Drake Milligan's most-recent AGT performance, the young Texan didn't mind.

The 25-year-old isn't aiming to please reality TV judges this time.

"(It) was a good victory lap, if you will," he tells Taste of Country about January's appearance on television.

  • Milligan appeared on NBC's AGT Fantasy League on Jan. 8.
  • He finished third on Season 17 of AGT in 2022.
  • The new Jukebox Songs EP drops Friday (Feb. 16)

"Don't Leave Me Loving You" — the song Milligan played for Cowell and America — is one of four new songs on his Jukebox Songs EP. The set deviates from his critically acclaimed debut album in two important ways: it's much shorter (obviously), and he didn't write but one song.

That second part came naturally, which says a lot about how far the "Sounds Like Something I'd Do" singer has come.

“Songwriting for me was a process of finding my own sound," he says. "Who I was as an artist — a lot of that work was done through songwriting.”

"I’ve always gravitated towards songs that feel classic. Songs that you hear and — in a good way — you go, ‘I feel like I’ve heard this before.'"

That said, it's probably unfair to label Jukebox Songs as fully realized Drake Milligan, but the songs he chose do represent an artist instead of a singer-songwriter. Strong storytelling, a willingness to collaborate with others and being able to identify hits are important skills that separate wheat from chaff in country music.

"When I was looking for songs or writing songs, I just wanted to find those classic-sounding songs that would fit on some jukebox, right next to our favorite jukebox songs," he says during a phone call. "Songs like 'Neon Moon' and 'Should've Been a Cowboy.'"

Few country fans will deny that aiming for Brooks, Dunn and Keith is a more worthy goal than trying to please Cowell.

Cover of Drake Milligan's Jukebox Songs EP
Stoney Creek Records

Jukebox Songs represents a change, not a pivot. Milligan still writes furiously, but now writes smarter. He'll set aside time when he's fresh to bring a good idea home, instead of doing it on the road or amid one hundred other responsibilities.

"I heard Chris Stapleton explain it one time that songwriting for him is an affliction," he tells Taste of Country. “As soon as he shuts it off, he’ll hear something and it’s right back. That’s kind of how I am."

The up tempo "I Got a Problem" joins heartbreaker "Don't Leave Me Loving You" as pre-released songs. "What I Couldn't Forget" and "Jukebox Songs and Barstool Beers" round out the collection.

Listen and try to guess where Milligan set his pen. If you're wrong, he's on the right track.

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