On May 27, 2008, Darius Rucker made the jump into country music: Fourteen years ago today, he released his debut country single, "Don't Think I Don't Think About It."

By that time, Rucker was a decorated musician who had already experienced multi-platinum success in the 1990s with the pop-rock band Hootie & the Blowfish. "Don't Think I Don't Think About It" was Rucker's first country single, but it wasn't his first solo single: Back in 2002, he released a solo album, Back to Then, that took inspiration from soul and R&B.

The easygoing "Don't Think I Don't Think About It" is pure country, however: Wistful pedal steel, lively fiddle and Southern-flecked acoustic and electric guitars cushion Rucker's voice, which boasts more of a twang than it did with Hootie & the Blowfish. The song was co-written by Clay Mills, who, Rucker tells The Boot, "had this great idea" for the lyrical focus.

"Most love songs are about people pining for their loved ones to come back," Rucker explains. "But we wanted to make it known that this guy was fine. He just heard that this girl was getting married, and he was thinking about her."

Darius Rucker Don't Think I Don't Think About It single
Capitol Nashville

Indeed, the lyrics are riddled with "what ifs?" and ruminations on what might have been, had timing and circumstances been different: "I wonder if sometimes I cross your mind," Rucker sings. "Where would we be today / If I never drove that car away?" Later, he admits, "Don't think I don't have regrets / Don't think it don't get to me / Between the work and the hurt and the whiskey / Don't think I don't wonder 'bout / Could've been, should've been all worked out."

As Rucker notes to The Boot, however, "Don't Think I Don't Think About It" isn't a song about trying to rekindle a relationship: "It's not sappy; it's just a song that everybody's gone through," he says. "No matter how happy you are in your life, if you hear that your ex is getting married, you'll think about it! Not that you want them back or anything though."

"Don't Think I Don't Think About It" certainly did resonate with audiences: It hit No. 1 on Billboard's Hot Country Songs chart, making Rucker the first Black solo artist to top that chart since Charley Pride did so in 1983 with "Night Games." The song also peaked at No. 35 on the Billboard Hot 100, giving Rucker his first solo hit, and setting him up for what's been a wildly successful country career.

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