17 of the Greatest Winona Ryder Movies of All Time

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Mr. Deeds (2002)

While this film isn't a starring vehicle for the actress, she kills it as a sarcastic reporter feigning girl-next-door to get closer to Adam Sandler‘s Deeds. She plays reporter Babe Bennett who decides to go after Deeds for a story since he's a man who just inherited quite a bit of money from his famous uncle. Her fake school nurse act is hilarious as she just can't figure out how to actually be a good person. Luckily Deeds ends up showing her the way and everyone gets a happy ending! Definitely one of her lighter roles…