Nashville in 2003 was a weird time for country music. You had the giants like Alan Jackson and George Strait still holding the fort, but then this kid with unruly curly hair and a beat-up truck shows up. Dierks Bentley didn’t just walk through the front door; he kicked it down with a dobro-heavy riff that sounded nothing like the polished "hat acts" on the radio. What Was I Thinkin' Dierks Bentley wasn't just a debut single. It was a career-defining moment that almost didn't happen because of a rowdy night and a very angry Grand Ole Opry manager.
Honestly, if you were around back then, you remember the impact. That driving beat and the story of Becky—the girl in the "little white tank top"—felt more like a movie script than a three-minute song. But here is the thing: the song is actually based on a series of real-life bad decisions.
The True Story Behind the Song
Most people think "What Was I Thinkin'" is just a catchy narrative about a guy getting shot at by a girl's father. While that’s part of it, the track is a patchwork quilt of Dierks' own chaotic twenties. He wrote it at the Sony/Tree fire hall in Nashville with Brett Beavers and Deric Ruttan. They weren't trying to write a hit. They were just sitting around swapping stories about the dumbest things they’d ever done for a girl.
Dierks has admitted in interviews, including a notable appearance on CMT Storytellers, that the "Becky" character was inspired by a girl he dated while he was working as a researcher at The Nashville Network (TNN). Back then, he wasn't a star. He was a guy with a laminate pass that he used to sneak into the Grand Ole Opry House after hours.
Basically, he’d use his TNN credentials to go where he wasn't supposed to be, often bringing girls along for the ride. Pete Fisher, who was the manager of the Opry at the time, actually banned Dierks from the building. Imagine that—one of the future faces of country music was persona non grata at the genre's most sacred hall. It took the massive success of What Was I Thinkin' Dierks Bentley for that ban to finally be lifted. By 2005, he was inducted as a member. Talk about a full-circle moment.
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Breaking Down the Lyrics: Fact vs. Fiction
The song is a masterclass in "show, don't tell." You can practically smell the cornfield and hear the shotgun blast.
- The Tailgate: The line about her daddy having a "heart like a nine-pound hammer" and shooting the tailgate of the truck? That’s pure country gold, but it taps into that real-world fear of meeting a protective father when you’re up to no good.
- The White Tank Top: This might be the most famous wardrobe choice in country music history. Dierks told Billboard that after the song blew up, he started seeing sea of women in white tank tops at every single show. It became a uniform for the fans.
- The "Mountain of a Man": The fight with the guy with the "Born to Kill" tattoo? It adds that layer of "man, I'm in over my head" that makes the chorus—What was I thinkin'?—so relatable. We’ve all been there. Maybe not getting our teeth knocked out in a bar fight, but certainly wondering why we followed a crush into a bad situation.
The Becky Effect: Who Was the Girl in the Video?
You can't talk about this song without talking about the music video. It was shot in New Braunfels and Kingsbury, Texas, over three days in May 2003. The girl playing Becky is Lauren Elaine.
Interestingly, she didn't just disappear after the first video. She became a recurring character in the "Dierks Cinematic Universe," appearing in the videos for "How Am I Doin'," "Lot of Leavin' Left to Do," and "Am I the Only One."
Lauren Elaine wasn't just a random model; she was a fashion designer and actress who helped cement the visual identity of Dierks' early career. The chemistry worked so well that fans started to believe Becky was a real person they could go meet in South Alabama.
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Why the Sound Was So Different
At the time, country radio was leaning heavily into a pop-rock sound. Then comes this track with a heavy, driving acoustic guitar and a dobro (played by Randy Kohrs) that acts as the secondary lead singer.
Producer Brett Beavers made a gamble. He kept the production "crunchy." It wasn't over-sanitized. It had a bluegrass soul but a rock-and-roll heart. This "modern bluegrass" vibe became Dierks’ signature. It's why he could later release a full bluegrass album like Up on the Ridge and not lose his core audience. He had already introduced them to those instruments on his very first day.
Chart Impact and Legacy
By September 27, 2003, What Was I Thinkin' Dierks Bentley hit number one on the Billboard Hot Country Songs chart. It knocked off "It's Five O'Clock Somewhere" by Alan Jackson and Jimmy Buffett—no small feat for a newcomer.
It also crossed over to the Billboard Hot 100, peaking at number 22. Even today, over two decades later, it's usually the high point of his live set. The energy in the room shifts the second that opening riff starts.
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The song did more than sell records; it established a brand. Dierks wasn't the guy in the starched shirt and the giant hat. He was the guy with the dog (his famous dog, Jake, made his first appearance in this video), the truck, and the penchant for getting into just enough trouble to make a good story.
Understanding the Song's Lasting Power
If you're a songwriter or just a fan trying to figure out why this track sticks, it comes down to three things:
- Authentic Stakes: The danger feels real, even if it's played for laughs.
- Rhythmic Hook: The way Dierks delivers the lines is almost percussive. It’s not just singing; it’s storytelling with a beat.
- The "White Tank Top" Visual: It gave the audience something to latch onto and participate in.
Take Action: Exploring the Dierks Catalog
If "What Was I Thinkin'" is the only song you know by Bentley, you're missing the evolution of one of the genre's most consistent artists.
- Listen to "Bartenders, Etc.": This is the only song on his debut album that Dierks wrote entirely by himself. It shows his raw honky-tonk roots.
- Watch the "CMT Storytellers" Episode: He goes deep into the technical side of how they built the dobro hooks for the debut.
- Check out the "How Am I Doin'" Video: It’s the direct sequel to the "What Was I Thinkin'" storyline and features the return of Becky.
The best way to appreciate the track today is to listen to the Dierks Bentley self-titled album from start to finish. You’ll hear a young artist figuring out exactly who he wants to be, one "what was I thinkin'" moment at a time.