There’s a gentle life-lessons ballad called “Little Stuff” that wraps up Brent Cobb’s latest album Keep ‘Em on They Toes in which he sings about seeing “heaven in the clouds.” It’s not a metaphor. Cobb, a proponent of natural mind-altering substances, was on a mushroom trip beneath a tree near a river in Spokane, Washington, when he looked up and saw faces gazing down at him from behind the clouds.

“You can call it God or angels or whatever you want,” he says, “but I saw the faces beyond the sky. They look down atcha while they’re making the clouds and they smile atcha. They didn’t talk to me, but they looked at me reassuringly like, ‘I know. It’s cool, isn’t it?’”

At the same time he sensed he was being watched, Cobb was observing thousands of mayflies hatch nearby and fly a few yards to the river, only to be eaten by fish. He had an epiphany: “Perhaps to those mayflies, I’m that face looking at them going, ‘This is pretty cool, isn’t it?’”A month later, he picked up his pen to immortalize the transcendent experience in “Little Stuff,” singing in his distinctly South Georgia phrasing: “I thought I oughta might just write this down.”

Such a story may come across as loony-tune from more pedestrian songwriters. But Cobb has always been an enlightened figure, blessed with the gift of finding purpose and meaning in the smallest of details, be they mayflies on a river or initials carved in a rock wall. His 2016 major label debut, Shine on Rainy Day, turned heads with intimate character studies, and he made hazy nostalgia appear bright and vivid on the 2018 follow-up Providence Canyon, a country-funk road trip across his native Georgia. Both were produced by Dave Cobb, his Grammy-winning cousin.

For Keep ‘Em on They Toes, Brent Cobb followed the advice of the title track and mixed up the formula, working with producer Brad Cook (Waxahatchee, The War on Drugs) not in Nashville, but in Durham, North Carolina. The result is a record that blends the introspective vibes of Shine on Rainy Day and the jam sensibility of Providence Canyon with indie-folk production. Cobb says he wrote it from “a country place of mind.”

“Everything I’m a fan of that Brad has done is very sparse. He doesn’t use a whole lot,” he says of the album’s airy sound. “With these songs, I wanted the lyrics to be the star. I thought they were important and I didn’t want anything to be distracting from them.”

Along with detailing his mind-expanding journeys “over the rainbow,” as he puts it, Cobb dissects growing old and having kids (“Sometimes I’m a Clown”), celebrates the art of being an individual (“Keep ‘Em on They Toes”), and questions the responsibilities of having an artist’s platform in “Shut Up and Sing” and “Soapbox,” the former written with his wife Layne, the latter with his father.

While at times playful, the lyrics are decidedly mature, lending credence to a T-shirt for sale in Cobb’s merch store that sums up his brand as “Country Music for Grown Folks.” It’s a similar mindset to one Chris Stapleton voiced upon the release of the equally mature Traveller in 2015. (Clearly, the approach found an audience for him.)

“I’ve had moments where a songwriter or an artist that I’m writing with will go, ‘Well, that seems a little too aged. Let’s make it younger.’ There’s nothing wrong with that, but that’s just not the way that I wrote this album,” Cobb says. “But ‘country music for grown folks’ doesn’t mean you have to be an adult. You can be an old soul to put this life into perspective.”

For whatever reason, the real country vs. imposter country argument continues to rage in certain corners of the internet. It may raise an eyebrow to some then that one of Cobb’s most “country” new songs was co-written with Luke Bryan. The country-radio superstar and Cobb grew up down the road apiece from each other in South Georgia and, after Bryan made his exodus to Nashville, he shared some of what he learned with Cobb.

“Luke definitely took me under his wing in trying to figure out how to make a living making music,” says Cobb, who used to crash at Bryan’s house in those early days. Bryan, in fact, arranged Cobb’s very first co-writing session in Nashville and blew his hair back with his supple piano playing.

When Cobb began writing for Keep ‘Em on They Toes, he asked Bryan if he’d like to create together again. “I said, ‘It’s been 10 years. You want to give it another shot?’” Cobb recalls. Together they came up with “Good Times and Good Love.” “If I’ve learned one thing from my honky-tonk heroes/it’s when a girl like you shows up, a man settles down,” Cobb sings in the soulful track, accompanied by Bryan on piano. He declares the “One Margarita” singer doesn’t get a fair shake.

“When I would read terrible reviews on Luke, I would be like, ‘Man, these people just have no idea how great of a musician he is and how wonderful of a writer he is,’” Cobb says of Bryan. “He’s made a massive living off of writing [songs] for the market. Nobody can knock him for what made him successful because he was what made him successful. He’ll have a long career because he’s yet to reveal all of his cards.” Cobb says his dream is for Bryan to make a Ronnie Milsap-type piano record.

A few years ago, Cobb left Nashville for a return to Georgia, settling in a lake house that he and Layne owned since 2008. It’s where he does much of his writing these days and where he meditates on the 12 years it took for him to establish a strong enough career that he could move back home. His family is all nearby.

“I’m still able to make a living by writing songs, except I’m sitting here now in my little boathouse off of the Flint River and it feels like, I don’t know, like I did what I set out to do,” Cobb says.

He thinks back to the fleeting lifespan of those doomed mayflies and offers some stoner wisdom that suggests he’s happy with his 34 years so far.

“From their perspective, they’ve lived a hundred years. But from our perspective, they’ve only lived for a moment,” he says. “They’re probably satisfied.”