When Lainey Wilson sang, I’m five generations of blazing a trail on her No. 1 song “Wildflowers and Wild Horses,” she meant it literally. Her father, Brian Wilson, is a fifth-generation farmer in tiny Baskin, Louisiana. And the reigning Entertainer of the Year says that he lives up to the profession’s stoic archetype. Even after eight No. 1 hits, nine CMA Awards, and 16 ACM trophies, praise from Brian Wilson is still tough to come by. Recently, the “Watermelon Moonshine” singer, 33, revealed which song of hers earned her dad’s highly coveted approval.
Lainey Wilson Jokes It’s “Downhill From Here” After Compliment From Her Father
A year ago, Lainey Wilson released Whirlwind, the much-anticipated follow-up to 2022’s Grammy-winning Bell Bottom Country. Now that it has reached the Billboard 200’s Top 10 and the Top Country Albums’ Top 5, she reissued a deluxe version on Aug. 22. The latest edition includes five brand-new songs, including the single “Somewhere Over Laredo.”
Videos by American Songwriter
Playing off the iconic “Over the Rainbow” from the 1939 classic The Wizard of Oz, “Somewhere Over Laredo” is currently climbing the charts. But even if the song never reaches No. 1, it’s already given Wilson something no one can ever take away.
“My daddy don’t pass out compliments, I’ll tell you that,” Wilson said during a recent sit-down with Kelleigh Bannen of Today’s Country Radio. “But the other day he told me — we were sitting on my porch — and he said, ‘It don’t get no better than ‘Somewhere Over Laredo.’ I’m telling you, it don’t get no better than that.’”
It was a sweet moment, so of course Wilson immediately ruined it with self-deprecation. “I was like, great, so now it’s downhill from here,” she joked.
Brian Wilson is “A Man of Few Words”
Lainey Wilson has previously emphasized just exactly how infrequently her father doles out praise. I’m talking about like, the only way I knew that he liked a song of mine when I was little was if he was tapping his toe or not,” she told Taste of Country in October 2022.
That’s how Wilson knew she had nailed it with “Those Boots (Deddy’s Song),” off her 2022 album Bell Bottom Country.
“I played it for him and he was tapping his toe, so I was like, all rightt, check,” she said. “But then afterwards he said, ‘That’s pretty dang good.’ So I was like, ‘We’re getting somewhere!’”
Featured image by Jason Davis/WireImage
More Latest Music News & Stories
-

NEW YORK, NEW YORK – SEPTEMBER 29: (L-R) Bruce Watson and Luis Maldonado of Foreigner perform onstage during The Buoniconti Fund to Cure Paralysis 39th Annual Great Sports Legends Dinner on September 29, 2025 at the New York Hilton Midtown raised millions of dollars to support the pioneering work of The Miami Project to Cure Paralysis, a designated Center of Excellence at the University of Miami’s Miller School of Medicine and the world’s premier research center targeting spinal cord and brain injury and other neurological disorders and diseases. (Photo by Mike Coppola/Getty Images for The Buoniconti Fund To Cure Paralysis)







