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There is a saying, a successful cute guy with a plain or ugly wife is usually gay. jack benny (born benjamin kubelsky february 14, 1894 december 26, 1974) was an american entertainer, who evolved from a modest success playing violin on the vaudeville circuit to a highly popular comedic career in radio, television and film. ive read just about everything and am convinced benny was gay. He and his wife slept in separate bedrooms their entire marriage and adopted a daughter. Jack was a womanizer in that at a party he would rather hang out and talk to the girls. He was an extremely likable man and i think his show biz friends helped keep his gayness a secret. Jack benny has been listed as a level-5 vital article in people, entertainers. Gay was already in popular usage by then, although it meant more along the lines of effeminate than overtly homosexual. I think it is fashionable these days to accuse every old entertainer of being homosexual or bi. Jack benny was not gay! He was married to mary livingstone for over 40 years. Jack was simply playing a character that embodied every negative personality known to man. Openly gay, he now lives in sedona, arizona, where he established a community television station with his former spouse. Dennis, was first brought to delightful life by character star kearns, who also leant his talents to shows from the jack benny program to our miss brooks. jacks carefully cultivated persona portrayed him as a vainglorious cheapskate. In fact, the real jack was a warmhearted, down-to-earth do-gooder, according to his daughter, joan benny. the names of actors clifton webb and jack simmons (above) often get thrown into the mix when discussing james deans gay lovers, but little information exists about these rumored love affairs. If we had to create a rumored gay fling for james dean, it would have to be with paul newman. I enjoyed jack bennys television show when i was a kid and i also enjoyed listening to recordings of his radio shows. Benny had feminine mannerisms and some people claim that he was gay.