Shoes That Fit: Eight Years and Eight Albums Into His Career, Alan Jackson Steps Up to the Plate with a New Album and Hits His Own Brand of Home Run

“You know that country song, ’Who’s Gonna Fill Their Shoes?’ I don’t know whether I can fill ’em, but I’d sure like to try ’em on.” — Alan Jackson, liner notes from Here in the Real World, 1990.

In the eight years since Alan Jackson mused his hopes and fears into the liner notes of his debut effort in 1990, few can deny that among today’s country acts, he comes as close as anybody to filling the shoes of his heroes George Jones, Merle Haggard and Waylon Jennings. With more than 25 million albums sold, over 20 Number One singles, countless awards (including the Country Music Association’s Entertainer of the Year), and the fulfillment of virtually every professional dream he ever had, Alan Jackson in 1998 is perhaps the premiere torch-bearer of traditional country music, or, as he puts it, “I hope I’m keeping a little bit of traditional country music alive for the next generations so they’ll know what it is.”

Alan Jackson has made a habit of using his own music to tip his ever-present white hat to his heroes. Sometimes it’s been direct, as in 1991’s nods to George Jones in “Don’t Rock the Jukebox” and “Just Playin’ Possum”, as well as that same year’s tribute to Hank Williams, Sr., “Midnight in Montgomery.” Other times it’s been a little more subtle, as in recent years when he took Tom T. Hall’s “Little Bitty,” Charly McClain’s “Who’s Cheatin’ Who,” and the Roger Miller/George Jones composition, “Tall Tall Trees”, put his own trademark sound on them, and drove them all to the top of the charts. He hasn’t been afraid to stretch his musical wings beyond the “safe” areas of modern country radio, either. In 1994 he took Eddie Cochran’s pop classic, “Summertime Blues” straight to the Number One slot, and now, with the success of the spoken-word hit “I’ll Go On Loving You,” Alan is riding high atop the country charts yet again.

Tackling a spoken-word song was a risk, admits Arista Records, who signed Alan in 1989 and has grown and guided his career since it’s beginnings. It was a risk worth taking according to Senior Vice President of Marketing Fletcher Foster.

“Obviously, it wasn’t the most typical radio-friendly song that was on the album. We knew that it was a very special single. But we also knew that it was different, and that if it could catch on, it would be big. Obviously, it was.”

“I’ll Go On Loving You” is merely the tip of the iceberg of an album that is Alan’s most introspective and deeply personal to date. Much of High Mileage was recorded while Alan was facing the most painful personal crisis of his life, the near-collapse of his 18-year marriage to wife Denise.

“What was happening was, I couldn’t be happy,” he recently told USA Today. “I kept trying to let everything else make me happy. Maybe that’s why I’m successful. I worked so hard to get all this stuff to make me happy. Then that didn’t do it. It actually got worse…I isolated myself more.”

Alan and Denise separated for five months and began counseling. Luckily, the couple was able to identify their problems and begin to work toward solutions. In June they reconciled, and they will renew their vows on December 15, their 19th wedding anniversary.

High Mileage is a thoughtful, reflective work dealing largely with love–love lost, love longed for, new love, lasting love. From the loneliness of “Gone Crazy” to the light-hearted “Right On the Money,” it’s clear that Jackson has taken a lot of time to think about the various shades of love, and he’s colored the album with a whole range of art and emotion. In short, it’s still country music the way it’s supposed to be – from the heart, where we live, what we know about. Long ago when Alan tentatively wondered if there could be a place for him in country music, if maybe he could attempt to fill the shoes of the country greats before him, he was perhaps simply hanging on to his dream of making the music he loved. Looking back on his impressive achievements today, however, it’s safe to say that as long as Jackson continues to make straight-ahead music that keeps traditional country a constant in the changing face of the 90’s and the century beyond, those shoes will likely just keep getting more and more comfortable.