The 30 Best Country Road Trip Songs, RankedThe 30 Best Country Road Trip Songs, RankedChoosing the right music is essential to a successful road trip.Carena LiptakCarena Liptak
Songs That Make Fun of Country MusicSongs That Make Fun of Country MusicSome of country music's biggest hitmakers have cut songs that make fun of the genre they love. Billy DukesBilly DukesCarena LiptakCarena Liptak
Alan Jackson Covers ‘Your Cheatin’ Heart’ For Hank Williams’ 100th Birthday [Watch]Alan Jackson Covers ‘Your Cheatin’ Heart’ For Hank Williams’ 100th Birthday [Watch]Jackson celebrated the country legend's 100th birthday in the best way possible: With a song.Carena LiptakCarena Liptak
Alan Jackson Shares Story Behind 9/11 Anthem, ‘Where Were You (When the World Stopped Turning)’Alan Jackson Shares Story Behind 9/11 Anthem, ‘Where Were You (When the World Stopped Turning)’It came to him in the middle of the night.Billy DukesBilly Dukes
Alan Jackson Shares Touching Tribute After News of Jimmy Buffett’s DeathAlan Jackson Shares Touching Tribute After News of Jimmy Buffett’s DeathThe two men collaborated on one of Jackson's biggest hits.Sterling WhitakerSterling Whitaker
Remember Who Passed on ‘It’s Five O’Clock Somewhere’?Remember Who Passed on ‘It’s Five O’Clock Somewhere’?Alan Jackson wasn't even second in line!Sterling WhitakerSterling Whitaker
Comedian Dusty Slay Makes a Good Point About ‘It’s 5 O’Clock Somewhere’ [Watch]Comedian Dusty Slay Makes a Good Point About ‘It’s 5 O’Clock Somewhere’ [Watch]The bit is a fan favorite, as Slay points out a few things we take for granted about the narrator, the time of day and Buffett's participation in this classic.Billy DukesBilly Dukes
Alan Jackson Reflects on How His Love Story Inspired ‘Remember When’ [Watch]Alan Jackson Reflects on How His Love Story Inspired ‘Remember When’ [Watch]The singer's hit ballad "Remember When" turns 20 years old in 2023.Carena LiptakCarena Liptak
PICS: Alan's Yacht's for Sale!PICS: Alan's Yacht's for Sale!Fans will recognize it from his videos.Sterling WhitakerSterling Whitaker
34 Years Ago: Alan Jackson Signs His First Recording Contract34 Years Ago: Alan Jackson Signs His First Recording ContractOn June 26, 1989, the struggling young country singer signed his first recording contract.The Boot StaffThe Boot Staff