Songfacts®:

• Here, Cole Swindell recalls being captivated by a girl after she performs Jo Dee Messina's 1996 classic "Head Carolina, Tails California" at a karaoke night. By the end of verse 2, he's joined her on stage, and afterwards they spend the rest of the evening in conversation.
  
  Now, whenever Swindell hears "Head Carolina, Tails California" he fondly remembers his fellow '90s country fan and wishes they could meet again.
• Cole Swindell co-wrote "She Had Me At Heads Carolina" with Ashley Gorley, Jesse Frasure and Thomas Rhett. The original writers of "Heads Carolina, Tails California," Tim Nichols and Mark Sanders, get credited too, as it incorporates some lyrics from their song and uses its melody.
• Swindell recorded "She Had Me At Heads Carolina" for his Stereotype album. He and Rhett had the original idea for the song when they were writing while on tour together. However, the pair needed to get the permission of Tim Nichols and Mark Sanders to use "Head Carolina, Tails California" before they started writing the tune.
  
  "I had no idea if they were going to be cool with it or not," Swindell told Audacy's Katy Neal. "If they hadn't been, we wouldn't have done it."
• Once they got the green light from Nichols and Sanders, and Messina gave her blessing too, Swindell and Rhett could get started. With the deadline for Stereotype looming, they called upon Ashley Gorley and Jesse Frasure to help them write the song. "I've never been under that much pressure," Swindell admitted. "I was like, 'if we don't write it today, this ain't gonna happen.' So that was a different feeling, going in knowing we got to write it and not only do we have to finish, it's gotta be good."
• Zach Crowell produced "She Had Me At Heads Carolina," one of nine Stereotype tracks he helmed. Crowell also played the keyboards and sang backing vocals with Canadian country-pop singer-songwriter Madeline Merlo. The rest of the instrumentation is:
  
  Acoustic guitar: Ilya Toshinskiy
  Pedal steel guitar, dobro: Scotty Sanders
  Electric guitar: Devin Malone, Kenny Greenberg and Sol Philcox
  Banjo, mandolin: Devin Malone
  Bass: Jimmie Lee Sloas
  Drums: Nir Z
• Directed by Spidey Smith and filmed in Downtown Nashville, the high-energy video follows the song's storyline. When Swindell and two buddies walk into a bar on karaoke night, one of them falls for a girl singing Messina's song. Messina herself plays the bartender.
• When Swindell and Rhett were touring together, they talked about taking a song they loved and putting their own spin on it. After settling on "Heads Carolina" they found themselves with a problem: It's got Carolina and California in it, but both Swindell and Rhett are from Georgia. "The only angle that worked," Swindell told Billboard, was the idea of walking in somewhere and the girl be singing that song."
• "She Had Me at Heads Carolina" won both Single of the Year and Song Of The Year at the 2023 ACM Awards. Earlier in the night, Messina and Swindell had performed a mashup of Swindell's "She Had Me at Heads Carolina" and Messina's "Head Carolina, Tails California."