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
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