Jarrett debuted in the World Wrestling Federation (WWF) in late 1993 under the gimmick of "Double J" Jeff Jarrett, a country music singer who intended to elevate his singing career through his exposure as a wrestler. Jarrett's character would strut to the ring wearing flashing "Double J" hats and ring attire, and he punctuated his promos with the phrase "ain't I great?". He ended his interviews by distinctly spelling out his name ("That's J-E-Double-F, J-A-Double-R, E-Double-T!").

Jarrett made his pay-per-view debut in January 1994 at the Royal Rumble. At SummerSlam, he pinned Mabel. At Survivor Series, Jarrett competed in a 10 man elimination tag match. In January 1995, Jarrett had a brief feud with Bret Hart, ultimately losing to Hart on the January 23 episode of Monday Night Raw. At the Royal Rumble in Tampa, Florida, Jarrett defeated Razor Ramon to win the WWF Intercontinental Championship. In an effort to become a dual champion, Jarrett challenged Diesel for the WWF Championship in the main event of the February 20 episode of Raw, but lost the match. Razor Ramon received a rematch at WrestleMania XI which Jarrett lost by disqualification, but retained the WWF Intercontinental Championship. Jarrett was then joined by The Roadie, with the duo losing to Razor Ramon in a handicap match at In Your House 1. On April 26, 1995, the WWF Intercontinental Championship was declared vacant after a controversial ending to a match between Jarrett and Bob Holly. They had a rematch later that evening where Jarrett reclaimed the title. On May 19, Razor Ramon regained the title from Jarrett in Montreal, Quebec, but Jarrett won it back two nights later in Trois-Rivières, Quebec, making him a three-time Intercontinental Champion.

At In Your House 2: The Lumberjacks on July 23, 1995, Jarrett performed the song "With My Baby Tonight". Later that evening, Jarrett lost the WWF Intercontinental Championship to Shawn Michaels. Following the event, Jarrett left the WWF for 7 months.

Jarrett returned to the WWF in late 1995, feuding with Ahmed Johnson. Jarrett lost to Johnson by disqualification at the 1996 Royal Rumble and left the WWF shortly thereafter due to a contract dispute. Later that year, The Roadie revealed that he had in fact sung "With My Baby Tonight" and that Jarrett had been lip synching.

Jarrett returned to the WWF on the October 20, 1997 episode of Raw, delivering a worked shoot speech in which he criticized both Eric Bischoff and WWF Chairman Vince McMahon. He then briefly feuded with The Undertaker. Later, along with Jim Cornette, formed a stable of invaders. In March, Jarrett left Cornette's stable.

Jarrett went on to reprise his country music singer gimmick, introducing Tennessee Lee as his manager and the tag team Southern Justice (formerly known as The Godwinns) as his bodyguards. He redeveloped his habit of breaking an acoustic guitar over the heads of his opponents. At Unforgiven: In Your House, Jarrett once again sang alongside Sawyer Brown with their hit single, "Some Girls Do". In August, Jarrett abandoned his country singer gimmick and dismissed Lee. He and Southern Justice began feuding with D-Generation X, with Jarrett losing to D-X member X-Pac in a hair versus 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, and forming a tag team with Owen Hart. Hart and Jarrett were close friends and travel partners for years, so the team gelled almost immediately. Jarrett and Hart won the WWF World 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. 8 days after Hart was killed 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. As he was handed the title he yelled Hart's name in tribute to his friend. In mid-1999, Jarrett won and lost the WWF Intercontinental Championship on 2 more occasions.

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'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.

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