Drew Barrymore in '50 First Dates' / ' The Wedding Singer' Barrymore pulled double duty and played his love interest as Julie Sullivan in ' The Wedding Singer' and as Lucy Whitmore in '50 First Dates.' Odds of her actually dating Sandler’s character: High. Plus, she had amnesia in '50 First Dates' so she would forget his terrible jokes at the end of every day.Katie Holmes in ' Jack and Jill' We could have gone with Sandler in drag for this movie, but Katie Holmes seemed like a more attractive choice.Odds of her actually dating Sandler’s character: Moderately High.
These aren’t ranked by present day, just by their character in the movie. Deeds' Ryder played a reporter that was trying to get the inside story on Sandler, who was the recent recipient of a fortune.
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