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Shakespeare in the Park in Central Park (they don't only do Shakespeare - they do all kinds of things ... classical, American classics, musicals, it's always different). But that's only during the Summer. You would need to stand on line for tickets same day in the park or at the Public Theater on Lafayette. Go early. This Summer they are doing Shakespeare's 'Hamlet' and the rock musical 'Hair.'
http://www.publictheater.org/
Several other companies have free outdoor shows during the Summer as well. One good place to look is NYTheatre ... everyone lists their shows there.
http://www.nytheatre.com/
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