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The annual Williamstown Theatre Festival gala includes cocktails and dinner, along with special appearances or performances by Annaleigh Ashford (Sunday in the Park With George), James Naughton (Chicago), Mandy Patinkin (Homeland), Emmy Rossum (Shameless), Phillipa Soo (Hamilton), and others. This year the event honors Gary Levine, managing director of the Williamstown Theatre Festival in the 1980s and now president of programming at Showtime.

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