Actors Who Cross-Dressed On Screen: Which Star Looks Better as a Woman?

Rupert Everett – St. Trinian’s

This movie was actually an independent reboot following five prior movies made based on the work of cartoonist Ronald Searle. Rupert Everett played the role of the headmistress of a high school filled with problematic girls. Everett’s portrayal was hilarious but the film was received with ambivalent reviews.

Everett has had a prolific career, starring with legendary actress Julia Roberts on My Best Friend’s Wedding in 1997One of his current projects is in theaters. The Happy Prince has Everett playing the role of Irish playwright and poet Oscar Wilde, portraying him during his last years.

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