The third episode of Red Shoe Diaries featured Denise Crosby, Star Trek babe and granddaughter of Der Bingle. That makes it sound as if she had a squeaky clean image, but she did not. She had posed for Playboy some 13 years before she performed on Red Shoe Diaries. This, by the way, was the first of two appearances she would make in the series, playing two different characters. She was in her mid-30s.
She’s not the only Playboy-Crosby connection. From Wikipedia, about Dennis, Bing’s son:
“On May 4, 1958, Crosby married Pat Sheehan, a Las Vegas showgirl and model who had once dated his father shortly after his mother had died. She was also Miss San Francisco of 1950, Playmate of the month of October 1958, and part-time actress. Within days, Crosby was sued by another woman, Marilyn Miller Scott, over the paternity of her daughter, Denise Crosby. The sensational lawsuit lasted three years and ended with Dennis being ordered to pay Scott child support and legal fees. This and the marriage to Sheehan and other details caused deep embarrassment for both him and his father. Although Bing Crosby died when his granddaughter was 19, the two reportedly never met.”
Pat Sheehan’s Playboy spread seems to be disappointingly non-nude.