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I’ve had a look back, and I’m sure the answer is PLURAL, and the wordplay refers to the last five letters. You’ve correctly described it, and it refers to Danny La Rue, a well-known drag act at the end of the last century (died 2009). So it’s LA RU(E) (short man in a dress) + L (fifty), upset (upwards, it’s a down clue), i.e. LURAL

Thanks Quisling. I had (p)lural but didn't know about Danny La Rue. Makes sense now.