[4] Bentley stated that he was inspired by an incident that had occurred while he was working as a behind-the-scenes staffer at The Nashville Network in the late 1990s.

[5] Rick Cohoon of AllMusic gave the single a mixed review, comparing its sound and theme to David Lee Murphy's "Dust on the Bottle" and calling the song "catchy enough, yet overdone.

[2] In 2017, Billboard contributor Chuck Dauphin put "What Was I Thinkin'" at number four on his top 10 list of Bentley's best songs.

It tells the story of the song's events in retrospect as the narrator looks over the damage he incurred from his wild night with Becky (such as pulling a corn leaf from the undercarriage of his Ford Ranchero or looking at the scar he picked up from his fight with the "mountain of a man with a 'Born to Kill' tattoo", which apparently is Becky's ex-boyfriend) while wondering if it was really worth it.

The video features Lauren Elaine as "Becky", the white tank-top wearing "beauty from South Alabama".

It reached its peak position of number one on the Billboard Hot Country Songs charts dated for the week ending September 27, 2003.