McMichael appeared at ringside in the WWF for Lawrence Taylor at WrestleMania XI on April 2, 1995 in Hartford, Connecticut. Taylor was wrestling Bam Bam Bigelow and there were several football players at ringside to keep wrestlers from interfering in the match. During the March 20 episode of Monday Night Raw, McMichael provided guest commentary with Vince McMahon and would later brawl with Kama Mustafa, one of Bigelow's comrades. The fight was all over the arena floor and almost into the stands, knocking over the broadcast table, soon being broken up by personnel. Taylor ended up winning the later match.
In 1995, McMichael was hired by World Championship Wrestling (WCW). On September 4, 1995, he made his debut with the company as the pro-babyface color commentator on the premiere of WCW Monday Nitro, with Bobby Heenan fulfilling his typical pro-heel commentator role alongside lead broadcaster Eric Bischoff. McMichael would root for the popular wrestlers during matches, would bicker with Heenan on a regular basis, and brought his dog Pepe with him to the broadcast booth.
In April 1996, Ric Flair started hitting on McMichael's wife Debra, who would sit at ringside during WCW Monday Nitro. McMichael challenged Flair and Arn Anderson to a match with his partner Kevin Greene. He trained with Randy Savage, while Flair and Anderson got Heenan to be their coach for the match.
The match took place at The Great American Bash. During the match, Debra and Greene's wife were chased to the back by Woman and Miss Elizabeth, who were Flair's valets. Debra came back with Woman and Elizabeth, and she had a briefcase full of money and a Four Horsemen t-shirt. McMichael accepted it and hit Greene in the head with the briefcase. McMichael's first singles match was against Joe Gomez at Bash at the Beach.
He went on to feud with the Dungeon of Doom with the other Horsemen, and he had problems with Jeff Jarrett over the affections of Debra in late 1996 through early 1997. Woman would trash Debra, causing McMichael and Chris Benoit to step in each time. The turning point in the McMichael–Jarrett feud was at SuperBrawl VII. McMichael wrestled Jarrett, and if Jarrett won, he was an official Horseman. Debra interfered for Jarrett, so he would win. Then McMichael and Jarrett had to team, and they bickered at first but later became a solid tag team. McMichael wrestled two football players in 1997. He beat Reggie White at Slamboree and lost to Kevin Greene at The Great American Bash, which saw McMichael slapped by Greene's mother at ringside.
In July 1997, Jarrett was kicked out of the Horsemen, and Debra soon left McMichael for Jarrett. McMichael got his revenge when he defeated Jarrett for his WCW United States Heavyweight Championship on the August 21 episode of Clash of the Champions XXXV. Just weeks earlier, Arn Anderson had been forced to retire due to an injury, and Curt Hennig took his place in the Horsemen. At Fall Brawl, Hennig turned on the Horsemen and joined the nWo, during the WarGames match that the Horsemen were involved in. McMichael was handcuffed to the steel cage surrounding the ring along with Chris Benoit, and neither man could defend Flair from the 5-on-1 assault from the nWo; the match ended after McMichael surrendered to stop the nWo from attacking Flair, although Hennig would still slam the cage door on Flair's head, even after the submission was made. The next night on Nitro, McMichael dropped his United States Title to Hennig, and Flair disbanded the Horsemen.
McMichael next went after Debra's stable of wrestlers that included Jarrett, Eddie Guerrero and Alex Wright. Debra hired Goldberg to get McMichael, and he became one of Goldberg's first victims in November 1997. Goldberg stole McMichael's Super Bowl ring and weeks later McMichael hit Goldberg with a pipe and reclaimed it. He briefly helped Benoit feud with Raven's Flock in January 1998, and then got into a feud with The British Bulldog, in which he broke his hand during a match at SuperBrawl VIII in February 1998. McMichael returned in June and had a feud with Stevie Ray and helped reform the Four Horsemen in October with Flair, Benoit, Dean Malenko and manager Arn Anderson. They feuded with the nWo until McMichael made his final appearance on the February 8, 1999 episode of Nitro.