Ten of Our Favorite Alan Jackson Songs

It's Hard to Narrow Down a List From His Massive Catalog of Hits

Once again, Alan Jackson is out there hitting the highways this summer, singing hit after hit after hit. He’s proven himself a durable entertainer over the last two decades, and it must be hard to narrow down a set list when you’ve got so many possibilities. Everybody has their favorite Alan Jackson songs. But when we are lucky enough to be in the audience, these are the 10 we want to hear the most.

“Chattahoochee”Aaaaaaa-yeeeeeee!!! When this song comes on the radio, I can’t help but picture Alan Jackson on water skis. Kids like it, too, even if they have no idea about why the young couple settled for a burger and a grape Sno-Cone. — Craig Shelburne

“Drive (For Daddy Gene)” — Like father, like son. It’s heartfelt, but not too sappy. I have those same fond memories of my grandfather letting me “drive” through his rural postal route, and I know I’d let my kids do the same thing. — CS

“I’ll Go on Loving You” — I think this is one of the sexiest and most beautiful songs I’ve ever heard: “When I look into your soft green eyes and when I see your delicate body, reveal to me as you slip off your dress.” … Don’t tell me you’re not hooked from the first line. — Whitney Self

“It’s Five O’Clock Somewhere” — I still get a big kick out of hearing Jimmy Buffett offer his cheerful wisdom. This is the ultimate summer vacation song, and it’s ridiculously fun in concert when everybody’s singing along. — CS

“Gone Country” — As funny as it is, I always thought this was an incredibly dark song until Bob McDill, the guy who wrote it, set me straight by explaining that this wasn’t his intention at all. Still, the message will remain timeless as long as people from New York and Los Angeles are still flocking to Nashville. I’m not sure anybody besides Alan Jackson or George Strait could have sung it and made it a hit. — Calvin Gilbert

“Here in the Real World” — Few people remember his first single, “Blue Blooded Woman,” but his second one set the tone for what we’d be hearing during the next 18 years. A real country song about the real world — co-written and performed by a real country singer. — CG

“Like Red on a Rose” — I think I’ve listened to this song on repeat for an entire day before. So often people try to describe love — using elaborate verbs and adjectives — but this song is composed of simple similes molded together to sculpt a love masterpiece. If anyone can put love into words, it’s Alan Jackson. — WS

“Livin’ on Love” — So many of his songs are so easy to sing along with, but this melody is irresistible. He and his wife Denise really did come from humble beginnings, and it’s easy for a lot of country fans to relate to that less-is-more lifestyle. — CS

“Remember When” — This song will forever remind me of my mother and father. We were driving along one afternoon and this song came on the radio. My father looked adoringly over at my mother and said, “Oh, honey, I think of you every time I hear this song.” About that time, Jackson sang the line, “You were the first, so was I / Made love and then you cried.” My mom looked back at him puzzled and said, “You weren’t my first!” — WS

“She’s Got the Rhythm (And I Got the Blues)” — What a great title and what a quirky rhythm. Between the lyrics and the musical arrangement, Jackson again nailed the honky-tonk sound that has served him so well. I had forgotten that he co-wrote the song with Randy Travis. — CG