CHIWETEL EJIOFOR AS LOLA IN KINKY BOOTS (2005)

Reason for cross-dressing: Ejiofor actually plays a stylish drag queen.
Complex says: Kinky Boots is a movie about a dude who saves his family shoe business by manufacturing heels for drag queens. It didn't catch too many American moviegoers' eyes, but Chiwetel Ejiofor in a wig and pumps didn't escape our eyes either.

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