THE BOOT: Top 5 Alan Jackson Videos!

Grand Old Opry member and Grammy Awards winner Alan Jackson has been a mainstay in country music for 25 years. From hit songs such as “I’d Love You All Over Again,” “I Don’t Even Know Your Name” and “Country Boy” to his numerous studio albums and 25th anniversary tour, the singer knows country music. And he know how to do it well.

While some artists excel at touring, and others are great at penning lyrics or acting in music videos, Jackson doesn’t really have a weak point. His very first CMA Awards win was for his “Midnight in Montgomery” music video, and time after time, Jackson’s revealed clips that are tender, fun and everything in between. The following, however, are our five favorites.

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Click the video title below to watch on Vevo!

1. Chattahoochee

2. Remember When

3. Midnight in Montgomery

4. Drive (for Daddy Gene)

5. It's Five O'Clock Somewhere