Jarrett went on to reprise his country music singer gimmick on the March 2, 1998 edition of Monday Night Raw, introducing Tennessee Lee as his new manager.
At Unforgiven: In Your House on April 26, 1998, Jarrett once again sang alongside Sawyer Brown with their hit single, "Some Girls Do".
On the June 1, 1998 edition of Raw, Tennessee Lee introduced Southern Justice (formerly known as The Godwinns) as Jarrett's new bodyguards.
Jarrett grew a goatee at that time.
On the August 9, 1998 edition of Sunday Night Heat, Jarrett fired Tennessee Lee after he had inadvertently cost Jarrett multiple matches in the preceding weeks.
Jarrett and Southern Justice then began feuding with D-Generation X (D-X), with Jarrett losing to D-X member X-Pac in a hair vs. hair match at SummerSlam.
Jarrett's long hair was subsequently cut short by D-X and Howard Finkel, who had himself been shaved bald by Jarrett and Southern Justice shortly before SummerSlam.
Jarrett and Southern Justice were defeated by D-X at Breakdown in September, and the trio separated shortly thereafter.

Jarrett briefly feuded with Al Snow before reuniting with Debra, who had left WCW for the WWF, and forming a tag team with Owen Hart.
Hart and Jarrett were close friends and travel partners for years, so the team jelled almost immediately.
Jarrett and Hart won the WWF Tag Team Championship from Ken Shamrock and The Big Boss Man, successfully defending the titles at WrestleMania XV before losing to Kane and X-Pac on an episode of Raw.
Eight days after Hart died in a stunt that went wrong at Over the Edge, Jarrett defeated The Godfather, who Owen was scheduled to face at the pay-per-view, for the Intercontinental Championship.
As he was handed the title belt, he yelled Hart's name in tribute to his friend.
In mid-1999, Jarrett exchanged the Intercontinental Championship with Edge and D'Lo Brown on two more occasions.
His fifth reign broke Razor Ramon's record from 1995.
He held the record until Chris Jericho's seventh reign in 2004.

In the months that followed, Jarrett became increasingly abusive towards Debra.
At SummerSlam, Jarrett challenged D'Lo Brown for both the WWF European and Intercontinental Championships, with Debra accompanying Brown to the ring following an argument with Jarrett.
Brown lost the match after both Mark Henry and Debra turned on him, making Jarrett the second ever "Euro-Continental Champion".
On the following episode of Raw, Jarrett rewarded Debra and Henry by giving Debra an assistant, Miss Kitty, and Henry the European Championship.
In late 1999, Jarrett began feuding with Chyna over the Intercontinental Championship.
In the course of the feud, Jarrett became somewhat misogynistic, attacking numerous females, including both wrestlers and actress Cindy Margolis, and executing the figure-four leglock on them.
Jarrett eventually abandoned Debra in favor of Miss Kitty after he and Debra were defeated by Stephanie McMahon and Test in a mixed tag team match.
He later also turned on Miss Kitty after she lost a match that Jarrett had inserted her into in his place.

Jarrett left the WWF in October 1999, right after WWF head writer Vince Russo resigned from the WWF in order to join WCW.
Jarrett's contract expired on October 16, 1999, one day before his scheduled match with Chyna at No Mercy.
Jarrett wrestled at No Mercy nonetheless, losing the Intercontinental Championship to Chyna.
Chyna later alleged that Jarrett and Russo had colluded in order to delay Jarrett's title defense until after Jarrett's contract had expired, and that Jarrett had subsequently made a deal with WWF Chairman Vince McMahon for $200,000 in order to wrestle at No Mercy without a contract.

In 2006, Jarrett asserted that he had been paid only what he was owed by the WWF.
In a 2008 interview for a TNA special, Jarrett stated that not only were his negotiations cordial and in good faith, but that he also got stock options in WWF's IPO, which occurred two days after he left.
Jarrett went on to reprise his country music singer gimmick on the March 2, 1998 edition of Monday Night Raw, introducing Tennessee Lee as his new manager. At Unforgiven: In Your House on April 26, 1998, Jarrett once again sang alongside Sawyer Brown with their hit single, "Some Girls Do". On the June 1, 1998 edition of Raw, Tennessee Lee introduced Southern Justice (formerly known as The Godwinns) as Jarrett's new bodyguards. Jarrett grew a goatee at that time. On the August 9, 1998 edition of Sunday Night Heat, Jarrett fired Tennessee Lee after he had inadvertently cost Jarrett multiple matches in the preceding weeks. Jarrett and Southern Justice then began feuding with D-Generation X (D-X), with Jarrett losing to D-X member X-Pac in a hair vs. hair match at SummerSlam. Jarrett's long hair was subsequently cut short by D-X and Howard Finkel, who had himself been shaved bald by Jarrett and Southern Justice shortly before SummerSlam. Jarrett and Southern Justice were defeated by D-X at Breakdown in September, and the trio separated shortly thereafter.
Jarrett briefly feuded with Al Snow before reuniting with Debra, who had left WCW for the WWF, and forming a tag team with Owen Hart. Hart and Jarrett were close friends and travel partners for years, so the team jelled almost immediately. Jarrett and Hart won the WWF Tag Team Championship from Ken Shamrock and The Big Boss Man, successfully defending the titles at WrestleMania XV before losing to Kane and X-Pac on an episode of Raw. Eight days after Hart died in a stunt that went wrong at Over the Edge, Jarrett defeated The Godfather, who Owen was scheduled to face at the pay-per-view, for the Intercontinental Championship. As he was handed the title belt, he yelled Hart's name in tribute to his friend. In mid-1999, Jarrett exchanged the Intercontinental Championship with Edge and D'Lo Brown on two more occasions. His fifth reign broke Razor Ramon's record from 1995. He held the record until Chris Jericho's seventh reign in 2004.
In the months that followed, Jarrett became increasingly abusive towards Debra. At SummerSlam, Jarrett challenged D'Lo Brown for both the WWF European and Intercontinental Championships, with Debra accompanying Brown to the ring following an argument with Jarrett. Brown lost the match after both Mark Henry and Debra turned on him, making Jarrett the second ever "Euro-Continental Champion". On the following episode of Raw, Jarrett rewarded Debra and Henry by giving Debra an assistant, Miss Kitty, and Henry the European Championship. In late 1999, Jarrett began feuding with Chyna over the Intercontinental Championship. In the course of the feud, Jarrett became somewhat misogynistic, attacking numerous females, including both wrestlers and actress Cindy Margolis, and executing the figure-four leglock on them. Jarrett eventually abandoned Debra in favor of Miss Kitty after he and Debra were defeated by Stephanie McMahon and Test in a mixed tag team match. He later also turned on Miss Kitty after she lost a match that Jarrett had inserted her into in his place.
Jarrett left the WWF in October 1999, right after WWF head writer Vince Russo resigned from the WWF in order to join WCW. Jarrett's contract expired on October 16, 1999, one day before his scheduled match with Chyna at No Mercy. Jarrett wrestled at No Mercy nonetheless, losing the Intercontinental Championship to Chyna. Chyna later alleged that Jarrett and Russo had colluded in order to delay Jarrett's title defense until after Jarrett's contract had expired, and that Jarrett had subsequently made a deal with WWF Chairman Vince McMahon for $200,000 in order to wrestle at No Mercy without a contract.
In 2006, Jarrett asserted that he had been paid only what he was owed by the WWF. In a 2008 interview for a TNA special, Jarrett stated that not only were his negotiations cordial and in good faith, but that he also got stock options in WWF's IPO, which occurred two days after he left.
Jeff Jarrett