Comedy Cellar

If the Village has a funny bone, this is where it gets tickled thanks to a star-studded group of alumni that includes Dave Chappelle, Chris Rock, Ray Romano, Jerry Seinfeld, and Damon Wayans. Arguably the most famous comedy club in Manhattan, the space is intimate (translation: seating is limited, so be sure to make reservations). If you're not into playing along, this might not be the spot for you, as many comedians incorporate audience members into their acts. If you visit during non-show hours, head upstairs to the pubby Olive Tree, which offers a full dinner menu and creative mixers like the white Russian shake. Two-drink minimum for shows. Shows are 18+ from Sunday to Thursday, but check the website for exact show times.