Hef and Carrie, shortly after his 1985 stroke

Next up chez Hef was another, and strikingly different, Canadian -- brunette Carrie Leigh, whose tempestuous liaison with Mr. Playboy tumbled over an obstacle course of uncontrollable events. Carrie was around for the Meese Commission witch hunt, the rise of right-wing religious zealots Jerry Falwell and Donald Wildmon, the tragic death of Playmate Dorothy Stratten, the poisonous feud with Dorothy's embittered lover, director Peter Bogdanovich, the closing of the Playboy Clubs and, in 1985, Hef's stroke.

Carrie was fascinating -- exhibitionist one day, devoted nurse the next. Hef, his longtime Executive Assistant Mary O'Connor remembers, was "nuts, absolutely nuts, over Carrie. We kept the couch in [Executive Vice President] Dick Rosenzweig's office loaded with presents from Daddy for Baby Boo." The affair ended in January 1988, when Carrie called from New York to tell Hef it was over. Subsequently, however, she filed -- and later dropped -- a palimony suit.