Cole Swindell Can 'Finally Check All the Boxes' with New Music and New Love: 'A Lot to Be Thankful For'

The country star's first date with his girlfriend was at a video shoot for one of his songs — and they’ve been together ever since

Before Cole Swindell's mom died in September, she routinely reminded the country singer to soak up his victories. Now, the 38-year-old Georgia native must remind himself, and he's had to do it a lot lately.

Swindell's recent No. 1 song "Single Saturday Night" was his 10th chart-topper and his current single "Never Say Never," a duet with Lainey Wilson, is poised to be among the biggest hits of his career. Both songs are from Swindell's new album Stereotype, which was released earlier this month. He was nominated for two trophies for "Never Say Never" with Wilson at Monday's CMT Music Awards, and the pair's rain-soaked performance on the show was well-received.

"She knew how much I wanted to be here and there and do this and be this on the ladder," he says of his mother, whose name was Carol. "She would say, 'You never dreamed of having one No. 1 when you moved to town.' I dreamed of it, but the fact that there's 10 of them, you almost have to stop and think because everything's moving so fast. I've tried to do that the past year, and you hear it every day — appreciate what you have. It's just human nature to want and wonder what's next."

Cole Swindell. Robby Klein

Swindell's fans have been wondering what's next for the last four years — the length between his third and fourth albums. Now they know. Swindell, whose other hits include "You Should Be Here," "Ain't Worth the Whiskey" and "Break Up in the End," co-wrote seven of the album's 13 songs, including co-writes with Thomas Rhett on "She Had Me at Heads Carolina" and HARDY on "Down to the Bar."

"She Had Me at Heads Carolina" is such a solid nod to Jo Dee Messina's 1996 hit "Heads Carolina, Tails California" that he asked permission and gave its writers credit on his song.

"It was the weirdest, coolest process I've ever been involved with," Swindell says of writing "She Had Me at Heads Carolina." He grew up listening to Messina's hit and says the song takes him back to happy memories in his hometown. He'd never put a new twist on a previous hit during songwriting before, and when he got the idea, he was intrigued. He knew it was a risk and that it could be terrible. But he also knew it could make the whole album.

"When me and Thomas Rhett were talking about it, we both knew it would be a huge idea, but we had to write it right. You can't mess up a classic hit like that," Swindell explains, adding that "She Had Me at Heads Carolina" was conceived as a duet Thomas Rhett would sing with him.

The song is about a girl singing karaoke in a bar, and in the ill-fated duet, Thomas Rhett would be Swindell's wingman. Given that Thomas Rhett is married with children, Swindell was uncomfortable with the idea. They wrote the best angle, and Swindell couldn't be happier with it. However, he hopes they'll find a way for Thomas Rhett and Messina to perform on the song one day.

"I'm gonna reach out to her personally and thank her for the original song," he says. The songwriters played Swindell's "She Had Me at Heads Carolina" for Messina, and when she texted to say she liked it, Swindell says, "We were all kinda freaking out."

"I can't wait to hopefully get her involved and give her the credit she deserves," he says. "Had she never sang that song; obviously, this wouldn't be on the album."

While "She Had Me at Heads Carolina" was a jigsaw of pieces to fit together, "Never Say Never," his duet with Wilson, fell into place. He wrote it with Jessi Alexander and Chase McGill on the last night of his first headlining tour. Swindell had never recorded a male/female duet, so the trio set out to write one. Alexander had the idea for "Never Say Never" saved in her phone, and they took the inspiration and ran with it.

Swindell loved the song when they finished it, but it took him years to find the person with whom he wanted to perform it. When Wilson shot to stardom with her debut hit "Things a Man Oughta Know," Swindell knew he'd found his duet partner.

"She's a phenomenal singer," Swindell says of Wilson. "It would not have been the same song without Lainey. I think it's a song that is connecting with people. Whether they want to admit it or not, a lot of people out there have been in relationships or done things that maybe it's not the smartest thing. You both know it, but it's just tough. You can't help who you love."

Cole Swindell and Courtney Little. The Tyler Twins

The album's title track, "Stereotype," about not judging people based on appearances, is another of Swindell's favorites. However, it's a song Swindell didn't write — "Some Habits" from writers Chris LaCorte, Josh Miller, Scooter Carusoe — that may be his most sentimental song on the album. The song's video led to his relationship with his girlfriend, Courtney Little. Swindell says he used to sing the song and think the lyrics were him to a tee, except the lines about love. He was talking to Little at the time, but they weren't yet in a relationship. He asked her to play his love interest in the song's video.

"That was kind of like our first date," he says. "Pretending like you're in a relationship on camera — that was pretty awkward. That was the first time we really got a chance to hang. We went out after we shot the video, and we've been together ever since. It's a pretty, pretty wild story, but you never know. They say songs are powerful. I feel like now, after meeting her, I can finally check all the boxes."

Now when he looks at his life, Swindell knows his mom was right — he just has to take a step back and remember what he's accomplished.

"I have a lot to be thankful for," he says. "I moved to Nashville with a dream, and if it all ended tomorrow, I think a lot of people would be surprised that I even got this far. That took moving out of my hometown. It took leaving school and just a lot of things. I didn't know it for a while, but it turned out to be worth it."