In modern society, men who dress up as women rarely do it to fool anyone. At least, we have to assume that because they're doing an absolutely awful job otherwise. In these ten works of fiction, the cross-dressers are doing no better, yet all of them managed to fool dozens of unsuspecting dupes.
10-Daniel Hillard played by Robin Williams from Mrs. Doubtfire
If you didn't DOUBT the effectiveness of Daniel Hillard's disguise, you should probably be set on FIRE (see what I did there). While the costume certainly makes Robin Williams less recognizable, it does a less admirable job at making him appear authentically human. In fact, I've seen mountains on Mars that look more human than that. If there is one thing that says you're fit to have custody of your children, it's sneaking into your ex-wife's house by posing as an elderly Scottish woman via cross-dressing.
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