3. Romy and Michele's High School Reunion: This 1997 comedy had Cumming starring opposite Mira Sorvino and Lisa Kudrow. Cumming starred as Sandy Frink, who adored Kudrow’s character, Michelle, all through high school despite her shooting him down repeatedly. Cumming went for the subtle approach as he played the mousy nerd in high school but the more confident billionaire at the fateful reunion. He made the character unforgettable especially during the end dance scene at the reunion with Kudrow and Sorvino.
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