Country Music Hall of Fame-er Alan Jackson has been performing live since starting a band after high school -- though, now, he's performing on much bigger stages. Jackson signed his first record deal in June of 1989, and while his debut single failed to chart, his first album, Here in the Real World, spawned four Top 5 singles -- including the No. 1 "I'd Love You All Over Again" -- and launched Jackson into life as a country star.

As any major artist does, Jackson has spent plenty of time out on the road and performing at festivals and awards show. These days, he still routinely tours, but it's cool to see what he looked like onstage in those early years. During the 1990s and early 2000s, Jackson played New York City's famed Beacon Theatre and CBGB; stopped by The Tonight Show With Jay Leno frequently; and was asked to perform during a number of awards shows.

Flip through the photo gallery below to see 20 old-school photos of Jackson onstage. Fans can visit his official website to find out where he's headed on tour next.

Test Your Alan Jackson Knowledge!

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