100 Greatest Men: #22. Alan Jackson

Alan Jackson100 Greatest Men: The Complete List

Since arriving on the country music scene in 1989, Alan Jackson has become one of the most critically acclaimed and commercially successful superstars to ever call country music home.  Amazingly, in this modern era, he did it all as a traditionalist.

Hailing from small town Georgia, Jackson started with singing gospel, but by his teenage years, he was already part of a local country duo.  He worked odd jobs while performing with his country band, and got his first big break when his wife, Denise, passed on his demo tape to Glen Campbell after a chance meeting in an airport.  He encouraged them to move to Nashville, and Jackson continued to work odd jobs while honing his craft as a singer and songwriter.

By 1989, he was the flagship artist of Arista’s new country division, and after a false start with “Blue Blooded Woman”, he scored a major hit with “Here in the Real World.”   What followed was a nearly uninterrupted run of major hits, most of which Jackson wrote himself.  His albums consistently sold multi-platinum, with “Chattahoochee” powering his third set, A Lot About Livin’ (and a Little ‘Bout Love), past the six million mark, a height he would reach again with both of his greatest hits collections.  He was named the CMA Entertainer of the Year in 1995.

What followed was the normal slowdown of a superstar in the latter half of the nineties.  He continued to sell platinum and score big radio hits, but attention had moved on to younger and more pop-flavored acts.  His biggest notoriety during this period came when he went off-script at the 1999 CMA Awards, singing part of George Jones’ “Choices” as a protest to Jones not being invited to sing his full song on that year’s show. But it was at the same awards show two years later, in the wake of the September 11, 2001 terrorist attacks, that Jackson performed the song that came to him in a dream: “Where Were You (When the World Stopped Turning).”

The instant classic powered Jackson back to multi-platinum sales, and he dominated the award shows for two years on the strength of the follow-up hits “Drive (For Daddy Gene)”, “It’s Five O’Clock Somewhere” and “Remember When.”   Jackson continued to find great success at country radio, and received strong critical notices for two left turns in 2006: the gospel collection Precious Memories, and the smooth, Alison Krauss-produced Like Red on a Rose.

In recent years, Jackson’s topped the charts by collaborating with Zac Brown Band, started his own label imprint, and finally released the bluegrass album he’d wanted to record for years.  Jackson’s second gospel collection, Precious Memories II, was the top-selling Christian Album of 2014.   And in in a fitting final tribute, Jackson was chosen to perform “He Stopped Loving Her Today” to close the memorial service for his friend and influence, George Jones.

Essential Singles:

  • Here in the Real World, 1990
  • Chasin’ That Neon Rainbow, 1990
  • Don’t Rock the Jukebox, 1991
  • Chattahoochee, 1993
  • Livin’ on Love, 1994
  • Gone Country, 1995
  • Where Were You (When the World Stopped Turning), 2001
  • Drive (For Daddy Gene), 2002
  • It’s Five O’Clock Somewhere (with Jimmy Buffett), 2003
  • Remember When, 2003
  • As She’s Walking Away (with Zac Brown Band), 2010

Essential Albums:

  • Don’t Rock the Jukebox, 1991
  • A Lot About Livin’ (and a Little ‘Bout Love), 1992
  • Who I Am, 1994
  • Drive, 2002
  • Precious Memories, 2006
  • Like Red on a Rose, 2006
  • Good Time, 2008
  • The Bluegrass Album, 2013

Next: #21. Elvis Presley

Previous: #23. Charley Pride

100 Greatest Men: The Complete List


  1. Alan Jackson is one of those artists that got me hooked on country music. His style and sound, next to only George and Garth, defined country music in the 90’s, which was my childhood. I grew up driving around to the sounds of Alan, Garth, George, Brooks & Dunn on long car rides from Michigan to Georgia. I’d venture to guess that many others share the same influences I do and were brought into country music by artists like Alan Jackson. He is the last of a crop of mainstream musicians that strove to be both a true artist and country at the same time.

    Under the essentials list I’d add “Midnight in Montgomery”, still one of the most bone-chilling songs I’ve ever heard. Other Alan Jackson favorites of mine not listed include “I Don’t Even Know Your Name”, “A Good Year For the Roses” with George Jones, “Song For the Life” and an album cut “Buicks to the Moon”.

  2. I like some AJ but if I had to list my top 40 country artists, he would not be included, but neither would Haggard, Jones, Cash or Jennings.

    Favorite AJ songs include Real World, Gone Country, 5 O’Clock Somewhere, Little Man, Remember When and the ZBB song Walking Away.

  3. Under the essentials list I’d add “Midnight in Montgomery”, still one of the most bone-chilling songs I’ve ever heard.

    Yep. After all these years it’s still my favorite Alan Jackson tune; I like it even more than DAC’s “The Ride.”

    Can’t argue with the others on the list, or with Motown Mike’s or Leeann’s assessments. I always found it a bit odd that he had that post-Who I Am lull and then came back with Drive, which is IMO the strongest album of his career.

  4. To Bob,
    Really no AJ, Cash, Haggard? I am afraind to ask who would you put in their place. While not always my favorites, there is no denying their top places in the genre along wtih Jones, Wynette, Loretta & Dolly.

  5. I’ve never really cottoned to Alan Jackson. I’ve just always found his music kinda bland. I like the fact that he seems to respect traditional country music though. He’s shown that time and again, in fact. From the aforementioned “Midnight in Montgomery” to “Murder on Music Row” to his performance of “He Stopped Loving Her Today” at George Jones’ memorial service.

    I’ll paraphrase my favorite Alan Jackson quote regarding modern country music: “Not all country music has to sound like Hank Williams … but some of it should.”

  6. …alan jackson at #22? now i’m awake for the rest of the countdown like someone walking around in shorts and flip flops in minnesota around january 15.

  7. I can’t believe that Alan Jackson didn’t even break the top 20. I’m a little disappointed, because AJ is one of my all-time favorites, second only to King George himself. At the same time, like Tom, I’m very interested to see who lands in front of him.

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