Songfacts®:

• During the height of the COVID pandemic, Oliver Tree spent six months at his grandparents' cattle ranch in Northern California. His second album, Cowboy Tears, was inspired by his time there, where he got in touch with his inner cowboy.
• The record's opening track, "Cowboys Don't Cry," has a message that it's okay for tough guys to shed tears. Tree wrote the country-pop song just after ending a relationship when he was crying his heart out. "Everyone needs to cry," he told Apple Music. "But specifically, men are taught not to cry and to just toughen up. And the truth is, yeah, you got to be a tough cookie, but inside that cookie, you need a very soft inside cookie that's just been cooked in the oven. You need to have a very, very sensitive side that comes with that hard exterior."
• The song recounts the heartbreaking end of a relationship when two people are fruitlessly trying to make it work.
  
  We're riding around this carousel
  Getting dizzy 'til we're sick
  Love is like a circle
  There's no easy way to end
  
  Tree compares the struggle to end a romance to riding on a carousel: It's initially fun but if you spend too long riding in circles, you end up feeling ill. He said it's about "the acceptance of that and learning how to try to be happy on your own."
• Oliver Tree usually records rock, hip-hop, pop, or electronic music, but "Cowboys Don't Cry" is a different genre. "This was my first country song I ever made. I proved to myself and my haters that Oliver Tree is not to be pigeonholed," he said. "He doesn't make music to appease anyone, not even his own 'fake' fans who turned on him when he announced he would return from retirement to make the greatest country album ever made."
• Oliver Tree co-wrote and co-produced the song with:
  
  Nine Inch Nails and Angels & Airwaves drummer Ilan Rubin.
  
  Producer Imad Royal (Panic At The Disco's "Hallelujah," Doja Cat's "Boss Bitch").