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

Whoopi Goldberg – The Associate

Whoopi Goldberg might as well be one of the most recognized personas of the century with her lengthy career and hundreds of appearances here and there. She first became recognized in the ’80s with Steven Spielberg’s movie The Color Purple and has since managed to win multiple awards for her talents.

In 1996, Whoopi starred in the movie The Associate. She played the role of a woman who was trying to make it to Wall Street and decided to disguise herself as a white old man in order to succeed. The movie was such a hit, even Donald Trump made a cameo appearance!

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