SHAWN AND MARLON WAYANS AS BRITTANY AND TIFFANY WILSON IN WHITE CHICKS (2004)
Reason for cross-dressing:
The Wayan's brothers play two FBI agents who disguise themselves as two rich heiresses to protect them. Imagine if the Feds really did shit like this? We'd want tax money back.
Another evolutionary moment in drag history: Black guys disguising themselves as white women. Reverse Racism? Maybe. All we know is this really didn't catch on like the fat suit did, which is surprising considering how popular white women in Hollywood have become over the years.