The Late Show Pod Show with Stephen Colbert

Guest: Lainey Wilson
Date: October 6, 2025

Overview

In this lively episode, Stephen Colbert sits down with Grammy Award-winning country singer and songwriter Lainey Wilson. They discuss her small-town Louisiana roots, journey to Nashville, rise in country music, and her new album "Whirlwind." The conversation is rich with humor, warmth, and Wilson’s trademark authenticity.

Key Discussion Points & Insights

Lainey's Small-Town Beginnings

• Growing up in Baskin, Louisiana:
  • Colbert marvels at Wilson’s upbringing in a town of just 157 people.
    • Lainey jokes: “Maybe 156 after I left.” (05:12)
  • Tight-knit family atmosphere—"they’re there when you need them and they’re there when you don’t. They’re just there.” (05:19)
• Early musical influences:
  • Wilson credits country music and storytelling in her upbringing.
    • “When you’re from a town of 157, you live your life on the edge of your seat, waiting for the next story. … I wrote my first song at 9 years old.” (05:54)
• First performances:
  • Made her first $20 singing at 9 years old at a convenience store opening.
    • “My daddy still has got the $20 bill.” (06:44)
  • Favorite childhood candy: “Anything chocolate. Sign me up. Reese’s Cups, Hershey’s, all of it.” (06:50)

Rodeo Roots & Family Wisdom

• Singing at rodeos and riding horses:
  • Wilson and her sister were PRCA rodeo flag girls; she often sang the anthem on horseback.
    • “I was on a horse before I could walk.” (07:30)
• Home comforts:
  • “That’s honestly where I feel most at home, is on the back of a horse and on a stage.” (07:33)

Nashville Journey

• Move to Nashville:
  • Wilson lived in a 20-foot camper trailer for her first three years in the city.
  • Mentorship from Jerry Cupid, who helped her get started by letting her park in his studio lot.
    • “I was known as the camper trailer girl.” (07:51)
    • “I’ve been in Nashville for 14 years.” (08:35)
• Handling adversity:
  • On keeping faith: “I’ve always had this weird sense of faith about knowing that this is what I was gonna do no matter what... It’s my calling.” (08:48)
  • Wilson’s parents’ support stood out: “What’s so weird is, my parents are pretty realistic, you know?... But they have always also known that I was gonna do it.” (09:14)

Career Celebrations & “Whirlwind”

• First Emmys experience:
  • Performed on stage with hero Vince Gill for her first Emmys. (04:39)
• Album talk:
  • "Whirlwind" is the title of her deluxe album, reissued in August.
  • Title inspiration: “The last few years, I feel like country music is finally starting to love me back as much as I love it. And it’s been a whirlwind.” (09:36)
• Song performance:
  • Previews her song “Somewhere Over Laredo,” an interpolation of “Somewhere Over the Rainbow.”
    • “If you say somewhere over the rainbow three times, it sounds like Laredo.” (10:06)
    • Inspiration comes from life on tour and reflecting while looking out airplane windows.
      • “A lot of song ideas happen… gave me an opportunity to step back into a pair of shoes that I wore a long time ago.” (10:18)

Notable Quotes & Memorable Moments

• On songwriting at a young age:
  • Lainey Wilson: “I was writing about tequila and cigarettes and like everything else… Old soul.” (06:18)
• On the Nashville hustle:
  • Lainey Wilson: “I lived in it [my camper trailer] for the first three years I was there.” (07:51)
• On unwavering belief:
  • Wilson: “It’s more than a hobby. It’s more than a passion. It’s my calling. And I knew that at 9 years old.” (08:48)
• On new album’s meaning:
  • Wilson: “The last few years, I feel like country music is finally starting to love me back as much as I love it.” (09:36)
• Stephen's perspective on small towns:
  • Colbert: “That’s not a small town. That’s a big family.” (05:14)

Timestamps for Key Segments

• [04:19] Lainey Wilson joins the show
• [05:06] Discussion of Lainey’s rural upbringing in Baskin, Louisiana
• [06:32] Early performances and first childhood earnings
• [06:58] Singing the national anthem at rodeos on horseback
• [07:42] Moving to Nashville, living in a camper trailer
• [08:48] Maintaining faith through adversity and parental support
• [09:28] New album “Whirlwind” and its inspiration
• [10:06] Description and background of “Somewhere Over Laredo”

Tone & Style

The conversation is joyful, full of Southern charm, humor, and mutual appreciation. Colbert’s wit and Wilson’s authenticity drive the episode, making it both entertaining and insightful for fans and newcomers alike.

Summary prepared for listeners who want all the heart and highlights of the conversation, minus the commercials and in-between banter.