On This Day in 2003, Alan Jackson Released a Massive Hit That Has Made Listeners Weep for More Than Two Decades

On this day (October 27) in 2003, Alan Jackson released “Remember When” as the second and final single from his 2003 compilation album, Greatest Hits Volume II. The song spent two weeks atop the Hot Country Songs chart in February 2004. Additionally, it peaked at No. 29 on the Hot 100, giving Jackson another crossover hit. However, for fans, this song is much more than its chart success.

Videos by American Songwriter

Jackson, a prolific songwriter, found a foolproof formula for hit songs early in his career. It was the same formula that the late, great Harlan Howard laid down long before the Georgia native released his first single: three chords and the truth. While Jackson may have added a few more than three chords, his first No. 1 single, “I’d Love You All Over Again,” was full of truth, straight from his heart. The same could be said about “Remember When.”

[RELATED: Alan Jackson Leaves Countless Country Fans in Tears with “Remember When” at the ACM Awards]

“I’d Love You All Over Again” is about the first ten years of the marriage between Alan and Denise Jackson. More than ten years later, he revisited the topic with “Remember When.” This song is from the perspective of an older man reliving his memories with his wife. In the song’s four verses, he sings about their first time together, their wedding day, the births of their children, raising a family, and growing old together. Like its predecessor, it is autobiographical. More importantly, it is a deeply moving song that has been pulling the tears from listeners’ eyes since its release.

Alan Jackson Makes Countless Fans Weep with “Remember When”

Alan Jackson received a diagnosis of Charcot-Marie-Tooth syndrome in 2011. The neurological disorder progressed slowly, allowing him to have another decade of touring and recording. In 2022, he announced his farewell tour. Then, earlier this year, he announced his final show.

Before taking his final bow, he appeared at the ACM Awards in May 2025. That night, he became the first recipient of the Alan Jackson Lifetime Achievement Award. Later that evening, he gave a moving performance that left nearly everyone watching in tears.

He could have chosen one of his bigger hits, like “Chattahoochee,” “It’s Five O’Clock Somewhere,” or “I’d Love You All Over Again.” Instead, he chose “Remember When.” Written as a reflection of a long and satisfying life with his wife and family, the song became a reflection on his career.

Featured Image by Rich Polk/Penske Media via Getty Images