A Wallace Shawn for Every Generation

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So I'm guessing:

Gen X: Princess Bride
Millennials & Gen Z: Rex from Toy Story
Gen Z / Alpha: Dr. Sturgis from Young Sheldon
Scifi Nerds: Grand Nagus Zek
Cinema Nerds: My Dinner With Andre
Theatre Nerds: Vanya, or any of his 15 (!) plays