Jerry Chesnut wrote the song in 1975, taking inspiration from a singer and pianist named Little David Wilkins. He said that, when writing the title, he thought of a woman walking through the door and causing trouble; he added that he spelled out the word "trouble", then the words "alone" and "looking", and found that they rhymed when spelled out.
The male narrator is a musician who performs various dance halls as a source of income, especially during late-night hours. During the middle of his performance at one particular hall, the narrator notices a rather attractive female entering the hall by herself without a guest. The male then begins to boast about the female's obvious quality and features as an attempt to catch her attention.
This song was recorded in 1992 by American country music singer Travis Tritt. It was the third single released from his 1992 album of the same name. It peaked at #13 in the United States, and #17 in Canada.
Geoffrey Himes, of Billboard magazine reviewed the song favorably, saying that Tritt transforms it with "boogie-woogie piano, slide guitar and super-fast tempo into a bar romp reminiscent of Little Feat."