The song sold 2,300,000 copies, making it the fourth-biggest single of her career behind "Jesus, Take the Wheel", "Before He Cheats", and "Blown Away".

After the end of her "Carnival Ride Tour", in February 2009, Underwood began writing songs for her new album Play On.

It incorporates elements of rock-inspired guitar riffs and background gang vocals in the introduction and verses, and also the violin and banjo-esque qualities which travel into the refrain.

Billboard reviewed the song favorably, stating that it "gives [Underwood] the chance to display the sassy side of her musical persona, which made previous hit "Before He Cheats" such an impact record.

[7] Matt Bjorke of Roughstock also gave a favorable review, saying, "Although the song borrows familiar melodic themes, the production is sparkling; Carrie sings the verses with rapid-fire precision and the hook is just infectious.

"[8] Kevin Coyne of Country Universe said that on “Cowboy Casanova”, Underwood makes a strong attempt but doesn't quite pull it off.

[15] The video was directed by Theresa Wingert and it features Underwood and an entourage of attractive female dancers all wearing flapper party gowns.

The man, a good representation of the song's topic, seemingly has designs on Underwood and as the video progresses the dancers become dressed in revealing clothing, consisting of garters and corsets.

Eventually, Underwood, along with her empowered entourage, has a showdown with the man in a back alley and defiantly spurns his advances, leading him to give up and walk away.