Demetri Martin will play Tiber, an aspiring interior designer in Greenwich Village obliged to run a Catskills motel; Imelda Staunton and Henry Goodman will play Tiber's parents; Jonathan Groff will play Woodstock organizer Michael Lang; Emile Hirsch will play a recently returned Vietnam vet, Eugene Levy will play farmer Max Yasgur, Liev Schrieber will play a transvestite named Vilma; Paul Dano and Zoe Kazan will play a hippie couple attending the concert; Dan Fogler will play a local theater troupe head; and Mamie Gummer will play Lang's assistant.

Lee won the Oscar for Brokeback Mountain and has directed such films as Crouching Tiger, Hidden Dragon.