In the fall of 1990, Boss Man began feuding with Bobby Heenan and The Heenan Family after Heenan continually insulted Boss Man's mother. He won a series of matches against Heenan Family members in 1991, including The Barbarian at the Royal Rumble and Mr. Perfect (via disqualification) at WrestleMania VII in an Intercontinental Championship match, which featured the return of André the Giant. At SummerSlam, he defeated The Mountie in a Jailhouse Match, a match in which the loser must spend a night in jail. This was the only such match ever held by the promotion. Boss Man then briefly feuded with Irwin R. Schyster.