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Hotel Metro
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This 14th-floor roof deck is surprisingly fun (especially considering the best neighborhood watering hole is probably the bar in Macy's), with cheap beer, an unpretentious after-work crowd, and occasional live jazz. Plus, the Empire State Building practically stands next to this laid-back party.
Best of New York: Fun & Nightlife
Cocktails at the movies, a Monday-night bacchanal, and a great rookie-rap show.