Twenty years ago today, on Sept. 27, 2003, Dierks Bentley earned his first No. 1 hit, with his debut single, "What Was I Thinkin'."

Bentley co-wrote "What Was I Thinkin'," which appears on his eponymously titled freshman album, with songwriter Deric Ruttan and his record producer and frequent collaborator, Brett Beavers. With lines such as, "She snuck out one night and met me by the front gate / Her daddy came out, wavin' that 12-gauge / We tore out the drive, he peppered my tailgate / What was I thinkin'?" Bentley says that the song was at least partly autobiographical.

Dierks Bentley What Was I Thinkin single cover
Capitol Nashville

"I was dating a girl that was a little bit younger than me," Bentley recalls of the inspiration for the song. "There was a father I had to meet every time I walked in the house. It was a little intimidating.

"We had so much fun writing it," he adds. "We wrote it pretty quickly."

"What Was I Thinkin'" ended Alan Jackson and Jimmy Buffett's seven-week run at the top of the charts with their duet "It's Five O'Clock Somewhere" (although they reclaimed the top spot one week later). The song has been certified gold, for sales of 500,000 copies, and also helped Bentley win an ACM Awards trophy for Top New Artist of the Year.

These days, with more than 20 hits to his credit, Bentley still features "What Was I Thinkin'" in his setlists. "I've been trying to beat that song for 10 years," he says.

Bentley included "What Was I Thinkin'" on his Greatest Hits / Every Mile a Memory 2003-2008 album.

This story was originally written by Gayle Thompson, and revised by Annie Zaleski.

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