It started with a white tank top. Honestly, most country music fans who were around in 2003 can still picture it. Dierks Bentley burst onto the scene with a messy, curly mane of hair and a song that sounded like a getaway car. Dierks Bentley What Was I Thinking wasn't just a debut; it was a mission statement. It told us exactly who this guy was: a little reckless, a lot of fun, and deeply rooted in a bluegrass-inflected sound that the radio hadn't quite figured out yet.
Most people don't realize how much of a gamble this track was.
Nashville in the early 2000s was leaning heavily into a polished, almost suburban "suburban cowboy" vibe. Then comes Dierks. He’s singing about a girl named Becky from South Alabama whose daddy "had a heart like a nine-pound hammer." It was gritty. It was fast. It had a dobro riff that felt more like a punch to the gut than a radio hook.
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The True Story Behind the Song
Believe it or not, the chaos in the lyrics isn't just creative writing. Dierks co-wrote the track with Brett Beavers and Deric Ruttan, and he’s been vocal about how it was inspired by his own questionable choices. Back when he was working behind the scenes at The Nashville Network (TNN), Dierks was known for being a bit of a troublemaker. He used his credentials to sneak into the Grand Ole Opry House just to hang out with the stars.
The "Becky" character? She’s based on a real girl he met during those TNN days. While the shotgun-blasting father might be a bit of "artistic license," the feeling of being mesmerized by a girl into doing something incredibly stupid was 100% authentic.
That Infamous Music Video
You can't talk about Dierks Bentley What Was I Thinking without mentioning Lauren Elaine. She played Becky in the video and became an instant icon in the country world. She wore the white tank top that Dierks keeps singing about, and the chemistry was so good they actually brought her back for three more videos: "How Am I Doin'", "Lot of Leavin' Left to Do", and "Am I the Only One."
The video itself was shot over three days in Texas. It captures that frantic, "morning after" realization perfectly. Dierks is sitting there looking at his beat-up Ford Ranchero, pulling corn stalks out of the undercarriage, trying to piece together how a single date turned into a high-speed chase through a cornfield.
- Release Date: April 14, 2003
- Chart Peak: #1 on Billboard Hot Country Songs (September 2003)
- Crossover Appeal: Reached #22 on the Billboard Hot 100
Why the Sound Was So Different
If you listen closely to the production by Brett Beavers, it’s not your standard Nashville fare. It’s loud. It’s "ragged," as Dierks likes to put it. There is a specific acoustic energy that bridges the gap between traditional bluegrass and modern rock.
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The song succeeded Alan Jackson and Jimmy Buffett’s “It’s Five O’Clock Somewhere” at the top of the charts. Think about that for a second. You had these legends of the genre being unseated by a kid with a signature acoustic guitar and a song about a girl with "ruby red lips."
The "Banned" Backstory
Here’s a fun piece of trivia: Dierks Bentley is supposedly the only artist to be banned from the Grand Ole Opry before he ever performed there. Why? Because of the trespassing he did while working at TNN—the very same antics that helped inspire the "what was I thinking" mindset of his debut. Eventually, they let him in, and he became a member in 2005. But that rebel streak is baked into the DNA of his first big hit.
What Most People Get Wrong
A lot of folks think this was just a "party song" that got lucky. That's a mistake. If you look at Dierks’ career over the last two decades, this song was the foundation for everything. It allowed him to take massive risks later, like his 2010 bluegrass album Up on the Ridge.
He didn't just want to be a star; he wanted to be a songwriter. He’s mentioned that "What Was I Thinkin'" was the last song he wrote for the debut album but the first one he recorded. It was a "beast" of a track that almost didn't happen because they were already looking at other material.
How to Capture the "What Was I Thinkin'" Energy Today
If you’re a songwriter or an artist, there are real lessons to be learned from this track. It’s about the "hook" being more than just a chorus. In this song, the dobro is the hook. The storytelling is the hook. The self-deprecating humor is the hook.
To really appreciate the impact, you should:
- Listen to the "Storytellers" version: Dierks performed this for CMT Storytellers recently, and hearing him break down the lyrics two decades later gives it a whole new weight.
- Watch the Becky Saga: Watch the four music videos featuring Lauren Elaine in order. It’s a rare piece of cinematic continuity in country music.
- Check the Credits: Look up Deric Ruttan and Brett Beavers. These guys helped shape the "Dierks sound" that defined the mid-2000s.
Twenty years later, the song hasn't aged a day. Every time that opening riff starts at a concert, the crowd still loses it. It’s a reminder that sometimes the best decisions come from the moments where you have absolutely no idea what you’re thinking.
For those looking to dive deeper into the Dierks Bentley catalog, start with the Greatest Hits or the Up on the Ridge album to see how that early bluegrass influence eventually took center stage. You can also follow his current "Stars & Strings" performances to hear how he's evolved the arrangement of his debut hit for modern audiences.