Stream It Or Skip It: ‘Lainey Wilson: Keepin’ Country Cool’ on Netflix, where the singer-songwriter looks at her journey while making a new map

“I spent a decade being the one you didn’t see coming.” Singer, songwriter, and Yellowstone appear-er Lainey Wilson is profiled in the Netflix documentary Keepin’ Country Cool, directed by Amy Scott, and the last time she did something like this – 2024’s Bell Bottom Country – Wilson hadn’t yet logged her second Grammy nomination, for the aptly-titled Whirlwind, or toured the world in support of that record. Keepin’ Country Cool joins Wilson on the road, highlights her connection with young fans, and takes off the cowboy hat and sequins to reveal the woman underneath, whose personal life has seen big changes, too. “The Lord was like, ‘You ain’t redneck enough, so I’m gonna send you a man named Duck.’” And he arrived packing an engagement ring.

The Gist: When Lainey Wilson was a little girl, growing up with her family in tiny Baskin, LA, she’d belt out karaoke covers in the living room and meticulously study the way Dolly Parton performed. In sit-down interviews for Keepin’ Country Cool, she says a lot of people still think she was an overnight success. But Wilson was always putting in work to pursue her calling. “I knew that I would be here – there is absolutely no doubt about it.”

“Here” is a world tour of arena shows, complete with a fleet of tour buses and support vehicles. “Here” is singing and playing guitar from atop a real-life, full-size pickup truck. And “Here” is featuring Lainey Wilson’s favorite part of any show, when she pulls a young fan from the crowd to be that evening’s “Cowgirl of the Night.” “I wanna remind these little girls of their self-worth,” she says. It’s a reminder for her, too. About what still matters, as the spotlight gets bigger and the expectations bolder.

Keepin’ Country Cool introduces Wilson’s longtime band, who keep her grounded with their memories of playing random gigs together. Her manager, Mandelyn Monchick, who is also a close friend. Her parents, her sister, and her nephews, who she jumps with on a backyard trampoline while still in her stage gear. And we meet Devlin “Duck” Hodges, former NFL quarterback and Lainey’s boyfriend. She calls it the healthiest relationship she’s ever been in, and when he’s interviewed separately, Duck shows us the ring he bought. 

There is also a big emphasis here on songwriting, as both the key driver of the extended Lainey Wilson Experience – celebrity photo shoots, brand partnerships, acting, promotional opportunities – and as a craft that requires constant attention. “For me,” Wilson says, “songwriting is taking care of my mind.” The featured writing sessions even include one for a song about Duck from the deluxe edition of Whirlwind, “Yesterday, All Day, Every Day.” It’s all part of her process, where the success is fantastic but also mentally and emotionally trying. Wilson figures writing about the simplest parts of her life puts it all in perspective. “I can’t be writin’ about a tour bus all the time, like the flashy part of my life. And to tell you the truth, I don’t want to.”

What Movies Will It Remind You Of? Lainey Wilson says her collabos have usually come out of IRL friendships, and two appear briefly in Keepin’ Country Cool, Jelly Roll and Post Malone. Both of those guys have their own documentaries.

This is also the latest music doc from filmmaker Amy Scott, who recently brought us Counting Crows: Have You Seen Me Lately? and also directed a pair of terrific profiles in Sheryl and Melissa Etheridge: I’m Not Broken.

With Keepin’ It Country, it’s also interesting to look back at where Lainey Wilson was in Bell Bottom Country, the Hulu special that was shot before Whirlwind came out – and before her engagement.  

Performance Worth Watching: Can it just be Hippie Mae Wilson? Lainey’s French bulldog is a fixture in Keepin’ It Country, and has also featured in her TikToks. At Lainey Wilson shows, fans make homemade “I Heart Hippie Mae” posters.  

Memorable Dialogue: “I’d been in Nashville for awhile,” Wilson tells her interviewer, “and I realized you can’t just be a decent singer-songwriter as a female. What else are you gonna do to get somebody’s attention? For me it wasn’t puttin’ on a strappy bikini and shorts going up my butt. I just couldn’t. And so, it was bell bottoms.”

Sex and Skin: Nah, but like with the above quote, Wilson is honest and thoughtful about the music industry, where somebody’s look and image are as important as their music and talent.

Our Take: “Songwriters cannot make a living on $.0009 streams alone.” We really appreciate Lainey Wilson’s candor about her job in Keepin’ Country Cool. This is not a music doc to showcase some unattainable baller life full of massive concerts, exclusive parties, private jets, and gated mansions. That stuff is fine, but it’s not her groove, and some of the best moments of Country include Wilson and her closest friends and collaborators just chilling at home. With her manager, she explains the frustrated economics of the modern music business model, which connects to so much of what we’ve seen her doing, from guest shots on Yellowstone to being an approachable, funny presence on her TikToks. It’s all part of the job, and since she has no intention of doing anything else, she’s gonna keep checking off boxes on her manager’s to-do list.

Instead of playing up the glitz and financial gains of a successful career in country music, Keepin’ Country Cool demystifies the whole thing, which we feel really does keep it cool. We can imagine one of those young fans from Lainey Wilson’s “Cowgirl of the Night” live segments being even more inspired by this clarity.

Our Call: Stream It! Lainey Wilson: Keepin’ Country Cool offers a solid profile of a musician who’s done the work to get where she is, and is trying to enjoy her success while staying true to what she’s always known. “People say country is cool again. Well, I say it never stopped being cool.”  

Johnny Loftus (@johnnyloftus.bsky.social) is a Chicago-based writer. A veteran of the alternative weekly trenches, his work has also appeared in Entertainment Weekly, Pitchfork, The All Music Guide, and The Village Voice.