Kelly was hired by the World Wrestling Federation (WWF) in June 1996. In 1997, Kelly, alongside Michael Cole and Jim Ross, served as the commentator for Raw is War, the flagship television program of the WWF. In 1999, Kelly began serving as an interviewer on Raw is War and SmackDown!.
As an interviewer, Kelly was involved in numerous angles. The most publicized was the controversial "Pillman's got a gun" angle, which took place on the November 4, 1996 episode of Monday Night Raw, which was filmed in Fort Wayne, Indiana. The angle was set against the backdrop of an ongoing feud between Brian Pillman and Stone Cold Steve Austin. Throughout the broadcast of Monday Night Raw, live footage was shown of Kelly interviewing Pillman in his home in Walton, Kentucky alongside Pillman's wife Melanie. After Dok Hendrix informed Monday Night Raw announcer Vince McMahon that Austin was supposedly traveling to Pillman's home, Pillman, upon being apprised of this development, produced and loaded a 9 mm Glock pistol. A frightened Kelly delivered the line "Pillman's got a gun!"
In the course of the interview, Austin arrived at Pillman's home and, after fighting off several of Pillman's friends who had surrounded the house to protect him, broke into the house and advanced on Pillman. Pillman responded by pointing his pistol at Austin, with the live camera feed subsequently fading to black as Kelly and Melanie Pillman screamed. When the camera feed returned, Pillman was being restrained by his friends, and Kelly informed McMahon that there had been two explosions, but no-one had been injured. At that point, Austin re-entered the house, with Pillman's friends forcing him out again as Pillman pointed his pistol at Austin while screaming obscenities and threats. Kelly shouted for someone to "call the police" as Monday Night Raw color commentator Jerry Lawler instructed him to "get the gun". The broadcast ended with Austin being driven from the house as Melanie Pillman cried.
In the late 1990's and early 2000's, Kelly would frequently be mocked by The Rock during interviews, with The Rock labeling him an "ugly hermaphrodite" and nicknaming him "Hermie". At Unforgiven on September 24, 2000, Kelly was attacked by the returning Stone Cold Steve Austin while attempting to interview him.
Kelly would later begin hosting the weekly WWF webcast Byte This!. In addition, Kelly produced WWE Confidential.
On March 21, 2003, Kelly was released by WWE as part of a series of budget cuts.