"Short of a man singing "I Enjoy Being a Girl" or "I Feel Pretty" in public you can get away with anything." A few years back, I saw a video on TV of Little Richard singing "I Feel Pretty" - it was hilarious and wonderful - he did the gender-changing thing: "Who's that pretty boy in the mirror?", etc. There is a well-established convention of females singing in the male voice (Jennifer Warnes also sang "Famous Blue Raincoat"), and I don't think anyone finds it disconcerting, as a general rule. However, to me it doesn't really work the other way, excepting in the singing of trad.(type) songs. Can't tell you why. Not that it's a secret; I just don't know why.
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