"A Lesson in Leavin'", also titled as "Lesson in Leavin'"', is a song written by Randy Goodrum and Brent Maher. It was originally recorded in 1980 by American country music singer, Dottie West, who brought the song to No. 1 on the Billboard Country Chart. In 1999, it was re-recorded by American country music singer, Jo Dee Messina, whose version spent seven weeks at No. 2 on the Billboard Country Chart.

Both versions of "A Lesson in Leavin'" are set at a mid-beat tempo. The song discusses how a woman is angry that her male lover has cheated on her. She hopes that the man's next lover treats him the way the woman was treated, saying that he will be given "a lesson in leavin."

Dottie West was the first singer to release the song as a single and titled it "A Lesson in Leavin'." West's version was recorded in country pop style that was apparent on most her singles in the 1980s. West's version peaked at No. 1 on the Hot Country Singles & Tracks chart the week of April 26, 1980, and was her first No. 1 hit as a solo artist, along with another No. 1 single shortly afterwards titled, "Are You Happy Baby?." In addition the single was reached No. 73 on the Billboard Hot 100 and was a minor hit on the Hot Adult Contemporary Tracks chart. The song helped to revitalize West's career, after having a series of unsuccessful solo singles in the 1970s. The song helped West endure popularity during the early 1980s.

Jo Dee Messina released a cover of West's original "A Lesson in Leavin'," but retitled the song, "Lesson in Leavin'." The song was released in 1999 as the fourth single from Messina's second album, 1998's I'm Alright. The song was a major hit in 1999, spending seven weeks at No. 2 on the Billboard Hot Country Singles & Tracks chart that summer.

"Lesson in Leavin'" debuted at number 56 on the U.S. Billboard Hot Country Singles & Tracks for the week of May 1, 1999.

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