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
31 Country Songs About Real Personal Tragedies31 Country Songs About Real Personal TragediesThese country stars turned devastating personal tragedies into music.Carena LiptakCarena Liptak
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
Top 10 Country Songs About SummertimeTop 10 Country Songs About Summertime"Summertime, and the livin' is easy" -- so goes the old American standard.The Boot StaffThe Boot Staff
32 Years Ago: Alan Jackson Becomes a Grand Ole Opry Member32 Years Ago: Alan Jackson Becomes a Grand Ole Opry MemberOn June 7, 1991, Jackson officially became a member of the Grand Ole Opry.Gayle ThompsonGayle Thompson
20 Years Ago: Alan Jackson and Jimmy Buffett Release ‘It’s Five O’Clock Somewhere’20 Years Ago: Alan Jackson and Jimmy Buffett Release ‘It’s Five O’Clock Somewhere’On June 2, 2003, Jackson and Buffett teamed up to release the pint glasses-clinking ode "It's Five O'Clock Somewhere."Annie ZaleskiAnnie Zaleski
Alan Jackson Lays Down Emotional ‘Where Were You’ for ‘National Memorial Day Concert’ [Watch]Alan Jackson Lays Down Emotional ‘Where Were You’ for ‘National Memorial Day Concert’ [Watch]The country icon sang the classic song in honor of 9/11's 20th anniversary.Natalli AmatoNatalli Amato
15 Songs You Didn’t Know Phil Vassar Wrote15 Songs You Didn’t Know Phil Vassar WroteYou know "Carlene" and "Just Another Day in Paradise," but did you know Phil Vassar also wrote these country hits for other artists?Lorie LiebigLorie Liebig
21 Years Ago: Alan Jackson Hits No. 1 With ‘Drive (For Daddy Gene)’21 Years Ago: Alan Jackson Hits No. 1 With ‘Drive (For Daddy Gene)’On May 25, 2002, Jackson earned his 20th No. 1 hit with "Drive (For Daddy Gene)."Gayle ThompsonGayle Thompson
Alan Jackson Welcomes New Son-in-Law: ‘Denise and I Are So Happy’Alan Jackson Welcomes New Son-in-Law: ‘Denise and I Are So Happy’The country legend celebrated with a sweet post about his new family member. Carena LiptakCarena Liptak
Keepin’ It Country: 20 Old-School Alan Jackson Live Shots [PICTURES]Keepin’ It Country: 20 Old-School Alan Jackson Live Shots [PICTURES]Country Music Hall of Fame-er Jackson has been performing live since starting a band after high school -- though, these days, he's performing on much bigger stages.Angela StefanoAngela Stefano
Alan Jackson’s Daughter Mattie Marries Connor SmithAlan Jackson’s Daughter Mattie Marries Connor Smith"Grateful is a gigantic understatement," Jackson shares on Instagram, promising a wedding picture drop soon. "Off to the islands with my husband!"Billy DukesBilly Dukes
PICS: Country's Best Mullets EverPICS: Country's Best Mullets EverThe style has had quite a comeback in recent years. JessJess
Every ACM Awards Album of the Year Award Winner EverEvery ACM Awards Album of the Year Award Winner EverAll 50-plus of 'em. Carrie HortonCarrie Horton
Jon Pari's Joining the Opry!Jon Pari's Joining the Opry!It was a historic moment.Sterling WhitakerSterling Whitaker
Alan Jackson’s $23 Million Oceanfront Mansion in Florida Is Jaw-Dropping — See Inside [Pictures]Alan Jackson’s $23 Million Oceanfront Mansion in Florida Is Jaw-Dropping — See Inside [Pictures]His ultra-high-end taste in property even extends to his vacation homes.Sterling WhitakerSterling Whitaker