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Jake Owen likes to compare changing record labels to free agency in professional sports. Like, say, NFL quarterback Aaron Rodgers, the "Barefoot Blue Jean Night" hit-maker was with a "team" for a very long time before he moved to a new team for a short time. That relationship began to fray so Owen stepped away and waited for the next opportunity, but, as he puts it, "My phone wasn’t ringing." Try to put yourself in the 44-year-old's shoes and let that sink in. You've been at it for two decades, notched nine Billboard Country Airplay No. 1 hits, headlined tours and festivals and remain plugged into what's working in country. However, you always lead with a confidence that, admittedly, masks some insecurities, and you've never really had the chance to make the album you want to make; the album that reflects your love of "real" country music. People just think you're the "Beachin'" guy, and that blade cuts twice. "In the last couple of years I’ve gone through my second separation, going back to being just this single guy, not having a team, a record deal. I was alone, dude. I felt really alone," he tells Taste of Country Nights host Evan Paul. "There were times where I felt like I had to get high so I didn’t cry," the musician adds. The second half of that sentence is a nod to his hero, Hank Williams Jr. In 1977, Hank released a song called "Feelin' Better" via The New South record. (More on that in a moment because you didn't come for a history lesson.) Amid his emotional crisis, Owen saw a post on producer Shooter Jennings' Instagram page. At this point (mid-2024), the two men had not met. In fact, Owen says he started to lean into a conclusion that Jennings—son of outlaw legend Waylon Jennings—heard songs like "Beachin'" and scoffed, but he dropped a comment anyway, asking something like, "Hey, when are you gonna make my record?" Within a day he got a DM. Then came a two-hour-long phone call. "This business is fickle. They’re always looking for the next thing. If it’s working, everybody’s all involved. If it’s not … it’s the next thing," Owen shares. "I got this feeling from Shooter, he was like, 'Dude you’re awesome. And I can’t understand why you haven’t made an album of these songs that you sit their on Instagram with your guitar and play,'" he continues. Dreams to Dream, out Nov. 7, is that album. It's filled with originals inspired by life and—"traditional" isn't quite the right word—old-school country music. This isn't bro-country, which Owen will proudly take credit for later. A few cover songs anchor him to a position far from public perception. "Them Old Love Songs" is one of them. Waylon Jennings cut the song in 1976 and Owen's version doesn't run from that time stamp. So now we're up to early 2025 and it's time to record. Jennings' studio is in Los Angeles but if you recall, wildfires were burning the city down at the time. Initially, Owen breathed a sigh of relief. He had the songs. He had a champion. He did not have the inner-confidence or harmony he'd hoped for. “I called Shooter, I’m like, ‘Hey man, there’s fires out there. Y’all still working?’" Owen recalls. "He goes, ‘Business as usual man, come on.’ He called my bluff again!” He flew in as everyone else was flying out, but flames beget flames and, "My life was on fire," Owen shares. Jennings and a five-piece band were waiting for him, and 13 songs later Owen came away with a sound he's proud to pivot to. It's not a reinvention as much as it is acknowledgement that we all grow old. "I'm 44 years old now. I want to sing mature music. I want to be real with the people that are my fans," he says. "How weird would it be for a 44-year-old guy to release a song now that's like, [sings] 'Whoa-oh, never gonna grow up...'?" the singer explains. With Dreams to Dream, Owen is "Feeling Better." The title track of the album actually hat-tips Hank's original but he shares that he identifies with every emotion on The New South. It's fitting, right? After all, Hank's big pivot was produced by Richie Albright... and Waylon Jennings.
