Actors Who Cross-Dressed On Screen: Which Star Looks Better as a Woman?
Adam Sandler – Jack and Jill

In the movie Jack and Jill, Adam Sandler played twin siblings. Jack is an ad executive and family guy who’s trying to survive Thanksgiving with his annoying sister Jill who came to visit. The movie was far from being a success and critics tore it apart.
It was the first movie in the Golden Raspberry Awards history to win every category. That includes the worst picture, worst actor, worst actress, worst director, and more. But hey, a paycheck is a paycheck, and Adam sure got one for starring in it—one worth $20 million, to be exact.
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