Rude made his World Wrestling Federation (WWF) debut on Superstars Of Wrestling on July 15, 1987 as the newest addition to the Bobby Heenan Family. His first feud in the WWF was with Heenan’s former muscle bound charge “Mr. Wonderful” Paul Orndorff (who Heenan had dropped after Rude joined the Family), before starting one of his most famous feuds with Jake “The Snake” Roberts. Rude had a routine where, before the match, he would make a show of removing his robe while insulting the males in the crowd (usually calling them “fat, out-of-shape sweathogs”) and, after his victories, he would kiss a woman whom Heenan selected from the audience. One of Rude’s trademarks was his specially airbrushed tights that he wore during matches. In the Roberts angle, Rude tried to get Roberts’ real-life wife, Cheryl, to participate (though not knowing when Heenan chose her that she was in fact Roberts’ wife). After Mrs. Roberts rejected him and revealed who she was there to see, Rude became angry (after she slapped him), grabbed her wrist, and berated her on the microphone when Roberts ran from the dressing room to make the save. To retaliate a few days later, Rude came to the ring with a likeness of Cheryl stenciled on the front of his tights. A furious Roberts charged the ring and stripped Rude, appearing to television viewers to leave him naked (as indicated by black-spot censoring Rude’s genital area), although the live audience saw him actually stripped to a g-string.
Through mid-1988 Rude continued to wear a second pair of tights under the one he wore to the ring, including during his match against the Junkyard Dog at the inaugural SummerSlam at Madison Square Garden. During the match Rude had the JYD on his back and had climbed to the top turnbuckle. While up there he pulled down his tights to reveal a second with Cheryl Roberts printed on them. After hitting the Dog with a flying fist, he was attacked by Roberts who had seen the action from the dressing room. Roberts attack on Rude caused the JYD to be disqualified, giving Rude the win. Rude’s feud with Roberts came to its conclusion when Roberts pinned Rude following a DDT during the 1988 Survivor Series.
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