Allied Domecq, Disguise
The much-beloved Fred the Baker character, who has represented Dunkin' Donuts in commercials since 1982, dons a dress to secretly find out what the grocery store competition is up to.
As Fred hastily throws on his wig, a shopper turns her daughter's head away. Fred, obviously in drag, covers his trademark mustache with a finger as he asks the grocery employees about their donuts--their eyes gape and jaws fall open in complete shock. A woman behind the counter even drops her loaf of bread in disbelief.
Of course, viewers are not shocked by Fred's behavior -- American culture has long allowed for straight men to dress as women, as long as they have an important goal.
This commercial was part of a campaign that won a Clio Award.