Dolly Parton entered a celebrity look-alike contest as herself and lost to a drag queen.
Parton told this story while discussing her 2012 memoir, Dream More. She entered a Dolly Parton look-alike contest at a Los Angeles gay bar without revealing that she was the real Dolly Parton. The other contestants were drag performers impersonating her, and the judges selected one of them over Parton herself.
The joke worked because Parton’s highly recognizable image—towering blonde hair, dramatic makeup, glittering clothes and an exaggerated silhouette—is itself closely associated with drag performance. She has also frequently expressed affection for drag culture, once saying that if she had been born male, she would have become a drag queen.
The anecdote is sometimes retold with varying details, including the venue, location and whether she placed second or simply lost. Those differences do not change the central fact or the canonical answer: it was Dolly Parton, not Madonna, Cher or Britney Spears.