The 30 Most Depressing Country Songs of All Time, RankedThe 30 Most Depressing Country Songs of All Time, RankedGrief, regret and hopelessness are three major themes in this countdown of the most depressing country songs of all time. Carena LiptakCarena Liptak
44 Years Ago: Alan Jackson Marries Denise Jackson44 Years Ago: Alan Jackson Marries Denise JacksonHappy anniversary to the Jacksons!Gayle ThompsonGayle Thompson
Kenny Chesney, Alan Jackson Lead Inspiring CMA Awards Tribute to Jimmy BuffettKenny Chesney, Alan Jackson Lead Inspiring CMA Awards Tribute to Jimmy BuffettThe heartfelt tribute turned into a singalong.JessJess
Kenny Chesney, Alan Jackson + More to Lead Jimmy Buffett Tribute at 2023 CMA AwardsKenny Chesney, Alan Jackson + More to Lead Jimmy Buffett Tribute at 2023 CMA AwardsIt's going to be a heartfelt moment.Sterling WhitakerSterling Whitaker
Alan Jackson Selling Spectacular $8.2 Million ‘Hullbilly’ Yacht — See Inside! [Pictures]Alan Jackson Selling Spectacular $8.2 Million ‘Hullbilly’ Yacht — See Inside! [Pictures]Fans will recognize it from his videos.Sterling WhitakerSterling Whitaker
See Inside Alan Jackson’s Incredible $19 Million Hilltop Estate [Pictures]See Inside Alan Jackson’s Incredible $19 Million Hilltop Estate [Pictures]It's a house fit for country music royalty.Sterling WhitakerSterling Whitaker
Remember When Loretta Lynn Dang Near Made Alan Jackson Blush? [Watch]Remember When Loretta Lynn Dang Near Made Alan Jackson Blush? [Watch]To look at him is to wonder if her words weren't worth more than the reason for the celebration. Billy DukesBilly Dukes
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