Songfacts®:

• Dierks Bentley's debut single tells the story of a wild night spent with Becky, a beautiful but wild girl from southern Alabama. Despite the reckless behavior she incites, Bentley finds himself captivated, and is swept up into a series of imprudent escapades.
  
  The chorus features the catchy hook, "What was I thinkin'?" as Bentley reflects on his questionable decision to get involved with Becky.
• Bentley co-wrote "What Was I Thinkin'" with his producer, Brett Beavers, and fellow country singer and friend Deric Ruttan. Bentley drew inspiration from a similar adventure he had with a woman he met while working as a behind-the-scenes staff member for CMT and TNN in the late 1990s.
• Bentley used his TNN credentials to sneak into the Grand Ole Opry House and mingle with country music stars. "We worked right next to the Opry," Bentley recalled to Taste Of Country. "It was out at Opryland and the building was right next to the Grand Ole Opry. So I would sneak over there on Fridays and Saturdays to watch the Opry before I would go down to Lower Broadway to watch more music."
  
  Bentley's unauthorized presence at the Grand Ole Opry House angered manager Pete Fisher, who banned him from the program. Fisher only lifted the ban after the success of "What Was I Thinkin'."
• The lead single from Bentley's debut self-titled album, "What Was I Thinkin'" became a massive hit, topping the Country chart. It was also certified two-times platinum by the Recording Industry Association of America (RIAA) for selling over two million copies in the United States alone.
• The song's success established Bentley as one of the rising stars of country music. Its rolling beat became the singer's signature sound, which he still embraced decades later.
• The Peter Zavadil-directed music video is a retrospective of the events that occurred during Bentley's wild night with Becky. We see the singer look back on the damage he incurred as he wonders if it was worth it. Zavadil filmed the visual over the course of three days in May 2003 in New Braunfels and Kingsbury, Texas.
  
  Lauren Elaine stars as the "beauty from South Alabama." Elaine reprises her role as the same character in other Bentley music videos for "How Am I Doin'," "Lot Of Leavin' Left To Do," and "Am I The Only One."