Alan Jackson was only two albums into what would become a legendary career when he received one of the most important career honors in country music. On June 7, 1991, Jackson was inducted into the Grand Ole Opry, just over a year after making his debut on the hallowed stage.

Jackson helped usher in a wave of new traditionalists in 1990 with the release of his debut album, Here in the Real World. The album spawned a string of hits including the title track, "Wanted," "Chasin' That Neon Rainbow" and "I'd Love You All Over Again."

He made his Opry debut on March 3, 1990, just days after the album's release on Feb. 27. Jackson — whose previous day job had involved delivering mail to the Opry — had always dreamed of playing at the country music institution, and he performed "Here in the Real World" during his debut.

Why Alan Jackson Is Country's Last Outlaw

Jackson's run of hits and genuine country approach soon made it clear he was an artist with a true commitment to traditional country values and a long career ahead. He released his second album, Don't Rock the Jukebox, on May 14, 1991, and just weeks later, Roy Acuff and Randy Travis were on hand to induct him into the Opry.

“The ultimate dream when you’re in country music is to be asked to join the Grand Ole Opry," Jackson reflects. “You think about people like Hank Williams, and Mr. Acuff, and George Jones, who stood on that spot of wood. That’s what makes you so nervous — to think about the historical part of the Opry and how it’s played such a part in country music.”

Sterling Whitaker is a Senior Writer and Senior Editor for Taste of Country. He focuses on celebrity real estate, as well as coverage of Yellowstone and related shows like 1883 and 1923. He's interviewed cast members including Cole Hauser, Kelly Reilly, Sam Elliott and Harrison Ford, and Whitaker is also known for his in-depth interviews with country legends including Don Henley, Rodney Crowell, Trace Adkins, Ronnie Milsap, Ricky Skaggs and more.

PICTURES: See Inside Alan Jackson's Massive Southern Manor Home

Alan Jackson's former 18,622-square-foot plantation-style estate sits on 135 acres in Franklin, Tenn., an affluent rural suburb outside of Nashville. The staggering residence includes formal dining and living rooms, a home office with maple floors, a spacious family room with 22 ft. ceilings, a gourmet kitchen with an adjoining breakfast room and a glass-enclosed porch on the first floor. There are four bedroom suites on the second floor, along with an exercise room and nanny quarters. The third floor has a game room, home theater and a custom pub. The property sold for $28 million in 2010, making it one of the largest sales of a private residence in Nashville.

Gallery Credit: Sterling Whitaker

PICTURES: See Inside Alan Jackson's Spectacular Hilltop Estate

After selling their spectacular Southern manor home in 2010, Alan Jackson and his wife moved to to what might be an even more impressive mansion, if that's even possible. Their 5-bedroom, 8-bathroom, 22,012-square-foot estate in the same Nashville suburb of Franklin features bedrooms that are all well-appointed suites, while the formal dining and living areas are finished off with splendid arched doorways, oversized windows and elaborate woodwork. The residence also includes a bar, a media room and multiple indoor and outdoor fireplaces. It sold for $19 million in March of 2021.

Gallery Credit: Sterling Whitaker

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