After country music changed toward pop music in the 1990s and 2000s, he and George Strait criticized the state of country music in the song "Murder on Music Row".
The song sparked debate in the country music community about whether "traditional" country music was actually dead or not.
 Despite the fact that the song was not officially released as a single, it became the highest-charting nonseasonal album cut (not available in any retail single configuration or released as a promotional single to radio during a chart run) to appear on Hot Country Singles & Tracks in the Broadcast Data Systems era, beating the record previously held by Garth Brooks' "Belleau Wood."
 The duo were invited to open the 2000 Academy of Country Music Awards (ACMAs) with a performance of the tune.
Rolling Stone commented on Jackson's style remarking, "If Garth and Shania have raised the bar for country concerts with Kiss-style production and endless costume changes, then Alan Jackson is doing his best to return the bar to a more human level."
After the September 11, 2001 attacks, Jackson released "Where Were You (When the World Stopped Turning)" as a tribute to those killed in the 9/11 terrorist attacks.
The country/soft rock song became a hit single and briefly propelled him into the mainstream spotlight; Jackson had debuted the song at the 2001 CMA Awards and his performance was generally considered the highlight of the show.
Jackson's website crashed the next day from server requests.
The song came to Jackson suddenly, and had not been scheduled for any official release, but the live performance began receiving radio airplay and was soon released as a single.
It was included on his 2002 album Drive, both the live version from his CMA performance, and a radio version.

Jackson released his second Christmas album (after Honky Tonk Christmas in 1993), titled Let It Be Christmas on October 22, 2002.
Jeannie Kendall contacted Jackson to do a duet, and he suggested the song "Timeless and True Love"; the song appeared on her first solo album, released in 2003.
In early 2006, Jackson released his first gospel music album entitled Precious Memories.
He put together the album by the request of his mother, who enjoyed religious music.
Jackson considered this album a "side project" and nothing too official, but it was ultimately treated as such.
More than 1.8 million units were eventually sold.

Just a few months later, Jackson released his next album, Like Red on a Rose.
Originally intended to be a bluegrass album, Like Red on a Rose had a different producer and sound.
Keith Stegall, was notably absent from this album and instead, Alison Krauss took over the producing reins.
Unlike Jackson's previous albums, the album abandoned Jackson's typical neotraditional country style and instead, went for a soft rock/adult contemporary sound.
This move proved controversial for his fans, who accused him of abandoning his signature style in order to go for a more commercial pop route.
Although critically acclaimed, the album was considered a commercial disappointment for the singer.
For his next album, he went back to his country roots.
Good Time was released on March 4, 2008.
The album's first single, "Small Town Southern Man", was released to radio on November 19, 2007. "
Country Boy", "Good Time", "Sissy's Song" and "I Still Like Bologna", were also released as singles. "
Sissy's Song" is dedicated to a longtime friend of the Jackson family (Leslie "Sissy" Fitzgerald) who worked in their house every day.
Fitzgerald was killed in a motorcycle accident in mid-2007.
After country music changed toward pop music in the 1990s and 2000s, he and George Strait criticized the state of country music in the song "Murder on Music Row". The song sparked debate in the country music community about whether "traditional" country music was actually dead or not.  Despite the fact that the song was not officially released as a single, it became the highest-charting nonseasonal album cut (not available in any retail single configuration or released as a promotional single to radio during a chart run) to appear on Hot Country Singles & Tracks in the Broadcast Data Systems era, beating the record previously held by Garth Brooks' "Belleau Wood."  The duo were invited to open the 2000 Academy of Country Music Awards (ACMAs) with a performance of the tune. Rolling Stone commented on Jackson's style remarking, "If Garth and Shania have raised the bar for country concerts with Kiss-style production and endless costume changes, then Alan Jackson is doing his best to return the bar to a more human level." After the September 11, 2001 attacks, Jackson released "Where Were You (When the World Stopped Turning)" as a tribute to those killed in the 9/11 terrorist attacks. The country/soft rock song became a hit single and briefly propelled him into the mainstream spotlight; Jackson had debuted the song at the 2001 CMA Awards and his performance was generally considered the highlight of the show. Jackson's website crashed the next day from server requests. The song came to Jackson suddenly, and had not been scheduled for any official release, but the live performance began receiving radio airplay and was soon released as a single. It was included on his 2002 album Drive, both the live version from his CMA performance, and a radio version.
Jackson released his second Christmas album (after Honky Tonk Christmas in 1993), titled Let It Be Christmas on October 22, 2002. Jeannie Kendall contacted Jackson to do a duet, and he suggested the song "Timeless and True Love"; the song appeared on her first solo album, released in 2003. In early 2006, Jackson released his first gospel music album entitled Precious Memories. He put together the album by the request of his mother, who enjoyed religious music. Jackson considered this album a "side project" and nothing too official, but it was ultimately treated as such. More than 1.8 million units were eventually sold.
Just a few months later, Jackson released his next album, Like Red on a Rose. Originally intended to be a bluegrass album, Like Red on a Rose had a different producer and sound. Keith Stegall, was notably absent from this album and instead, Alison Krauss took over the producing reins. Unlike Jackson's previous albums, the album abandoned Jackson's typical neotraditional country style and instead, went for a soft rock/adult contemporary sound. This move proved controversial for his fans, who accused him of abandoning his signature style in order to go for a more commercial pop route. Although critically acclaimed, the album was considered a commercial disappointment for the singer. For his next album, he went back to his country roots. Good Time was released on March 4, 2008. The album's first single, "Small Town Southern Man", was released to radio on November 19, 2007. "Country Boy", "Good Time", "Sissy's Song" and "I Still Like Bologna", were also released as singles. "Sissy's Song" is dedicated to a longtime friend of the Jackson family (Leslie "Sissy" Fitzgerald) who worked in their house every day. Fitzgerald was killed in a motorcycle accident in mid-2007.
Alan Jackson