3. Mr. Deeds
This 2002 comedy was loosely based on the 1936 film Mr. Deeds Goes to Town. This time around, Sandler played Longfellow Deeds, a small-town New Hampshire pizza parlor owner and all-around nice guy. Turns out he’s inherited $40 billion from an uncle he never met. Deeds flies to New York and hijinks ensued as he tried to fit in with the movers and shakers and met Winona Ryder’s Babe Bennett, a reporter, who poses as a school nurse to get close to Deeds but ends up falling for him. Sandler is endearing and genuine as Deeds navigates through the machinations of Chuck Cedar, played by While You Were Sleeping’s Peter Gallagher, who tries to dupe Deeds but fumbles against Deeds’ overwhelming honesty. Sandler’s honest portrayal of this wonderful guy made moviegoers remember why we fell in love with Sandler in the first place. In addition, Sandler and Ryder make a sweet yet comical pair on screen.
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