[3][1] In November 1999, Kelly debuted in the Delaware-based East Coast Wrestling Association as a manager, forming several heel stables.

[10] Kelly received a try-out with the World Wrestling Federation as a ring announcer due to the intervention of fellow IWF alumnus Billy Gunn.

[11] From August to October 1996, Kelly served as commentator for Raw is War, the flagship television program of the WWF, alongside Jim Ross and Jerry Lawler.

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.

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.

Kelly shouted for someone to "call the police" as Monday Night Raw color commentator Jerry Lawler instructed him to "get the gun".

[17][18] Kelly also had a minor degree of influence on the creative direction of the WWF, and was the creator of the storyline that saw Stephanie McMahon marry Triple H, creating the McMahon-Helmsley Faction.

[14][20][21] In 2004, Kevin Kelly would replace Joey Styles as the announcer for Major League Wrestling, but the promotion would cease operations shortly thereafter.

[27] He returned as part of NJPW English commentary at Invasion Attack 2016 alongside Steve Corino, who filled in Matt Striker's position.

[29] Kelly would leave the company on November 14 instead, he was replaced by American indendepent wrestling commentator Walker Stewart on English commentary.

[32] He was fired on March 8, 2024, after taking to social media the week before and accusing ROH and fellow AEW announcer Ian Riccaboni of libel and attempted career sabotage.

Kelly has also filed a lawsuit for monetary damages from AEW and Riccaboni for breach of contract, defamation and causing him to being unable to find work.