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 left 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.1 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?."2 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, blocked from the top spot by Lonestar's "Amazed".7
"Lesson in Leavin'" debuted at number 56 on the U.S. Billboard Hot Country Singles & Tracks for the week of May 1, 1999.
‡ Sales+streaming figures based on certification alone.
Sheridan, Tim. "Are You Happy Baby: The Collection album review". allmusic. Retrieved 2009-02-22. https://www.allmusic.com/album/r326013 ↩
Ankeny, Jason. "Dottie West > Biography". allmusic. Retrieved 2009-02-22. https://www.allmusic.com/artist/p1866/biography ↩
"Dottie West Chart History (Hot Country Songs)". Billboard. https://www.billboard.com/artist/Dottie-West/chart-history/CSI ↩
"Dottie West Chart History (Hot 100)". Billboard. https://www.billboard.com/artist/Dottie-West/chart-history/HSI ↩
"Dottie West Chart History (Adult Contemporary)". Billboard. https://www.billboard.com/artist/Dottie-West/chart-history/ASI ↩
"Best of 1980: Country Songs". Billboard. Prometheus Global Media. 1980. http://www.billboard.com/charts/year-end/1980/hot-country-songs ↩
Fabian, Shelly. "Jo Dee Messina Bio". about.com. Archived from the original on 2008-01-30. Retrieved 2009-02-22. https://web.archive.org/web/20080130123345/http://countrymusic.about.com/od/jodeemessina/a/bljdmessina_bio_2.htm ↩
"Top RPM Country Tracks: Issue 8473." RPM. Library and Archives Canada. August 30, 1999. Retrieved July 7, 2013. https://www.bac-lac.gc.ca/eng/discover/films-videos-sound-recordings/rpm/Pages/image.aspx?Image=nlc008388.8473&URLjpg=http%3a%2f%2fwww.collectionscanada.gc.ca%2fobj%2f028020%2ff4%2fnlc008388.8473.gif&Ecopy=nlc008388.8473 ↩
"Jo Dee Messina Chart History (Hot 100)". Billboard. https://www.billboard.com/artist/Jo-Dee-Messina/chart-history/HSI ↩
"Jo Dee Messina Chart History (Hot Country Songs)". Billboard. https://www.billboard.com/artist/Jo-Dee-Messina/chart-history/CSI ↩
"RPM Top 100 Country Tracks of 1999". RPM. December 13, 1999. Retrieved July 7, 2013. http://www.collectionscanada.gc.ca/rpm/028020-119.01-e.php?brws_s=1&file_num=nlc008388.9956&type=1&interval=24 ↩
"Billboard Top 100 - 1999". Archived from the original on 2009-07-09. Retrieved 2010-08-28. https://web.archive.org/web/20090709044506/http://longboredsurfer.com/charts.php?year=1999 ↩
"Best of 1999: Country Songs". Billboard. Prometheus Global Media. 1999. Retrieved August 25, 2012. http://www.billboard.com/charts/year-end/1999/hot-country-songs ↩
"American single certifications – Jo Dee Messina – Lesson in Leavin'". Recording Industry Association of America. Retrieved February 7, 2023. https://www.riaa.com/gold-platinum/?tab_active=default-award&ar=Jo+Dee+Messina&ti=Lesson+in+Leavin%27&format=Single&type=#search_section ↩