One of the most prolific and beloved artists in country music, Alan Jackson has been delighting fans and critics alike for over 30 years. With 16 studio albums, 10 greatest hits records and even two Christmas cuts, Jackson is one of the best-selling artists of the past few decades, selling over 40 million albums throughout his career.

Jackson released his debut album, Here in the Real World, in 1990. Four of that project's singles went to the Top 5 at country radio, and the project also yielded his first No. 1 hit, "I'd Love You All Over Again." The song was the first of a grand total of 26 chart-topping hits for the country star.

A member of the Grand Ole Opry as well as the Georgia Music Hall of Fame, Jackson was inducted into the Country Musical Hall of Fame in 2017. At the time, he called that high honor "the last dream on the list," adding "It's a mountaintop for a country singer."

With all that history, there are countless memories, hit singles, and highlights from Jackson's career. Scroll through the gallery below to see a few of The Boot's favorites.