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1. The rom-com was the first production for Drew Barrymore and Nancy Juvonen's Flower Films. "I wanted to make this movie because it taps into an emotion that everyone can identify with—the awkward moments of our high school years," the actress told Wild About Movies in 1999.
Coming off her work in Ever After and The Wedding Singer, it was a marked success for the former child star and led to a slew of other successful work. (See: 50 First Dates, He's Just Not That Into You, Whip It!) "I had fun but wanted to make it work," she told E! News of her first producing gig, "and then when it did I was allowed to make Charlie's Angels so each movie is a piece."