Watch Jo Dee Messina's Acoustic Take on Her Classic Dottie West Cover 'Lesson In Leavin'': Exclusive Premiere

Over the past two decades, Jo Dee Messina has been one of the most identifiable voices in the country format. Her expressive vocal approach has helped her gain hits with songs such as “Bye Bye,” “You’re Not In Kansas Anymore,” and “Stand Beside Me.” During the summer months of 1999, she achieved one of her biggest hits with a cover of a Dottie West classic, “A Lesson In Leavin.” Messina tells Billboard how her version of the song came to be.

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“The first time I heard this song I was watching the Dottie West story (1995’s Big Dreams and Broken Hearts) on TV and Tim McGraw, who co-produced the song, actually suggested I cut it because he said it sounded like me," explains Messina. "I am so glad that I did. I really enjoy performing it at shows and especially stripped down like this. It is still one of my favorites!" The song made a huge impact with her fan base, as well. The record spent seven weeks at No. 2 on Top Country Songs (held out of the top spot by Lonestar’s “Amazed”), and became one of her two entries into the top 30 on the Hot 100.

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Billboard has an exclusive premiere of a brand-new performance of Messina's hit, recorded for YouTube country channel Country Now, as part of the show’s Live From Blackbird series. The singer, who is currently on the road in support of her album ME, has been working on a brand-new single. Look for a special acoustic version of the new track coming soon to the channel.