RECOMMENDED: NYC's best late-night destinations
Emceed by a cohort of six local comics, this weekly show brings together stand-up, improv and sketch acts. Topics and prompts are totally random, but that's half the fun: Everything from peanut anatomy to finishing school for the modern woman (think beer bottles instead of books) is considered fair game. 153 E 3rd St between Aves A and B (212-366-9231, east.ucbtheatre.com). Fri 10:30pm; $10.
The Great American Songbook serves as the catalog for this weekly jam session. Pianist-singer Eric Yves Garcia plays selections from Gershwin, Ellington and other masterminds of the 20th century, as bar patrons and staff members sing along (usually on key). Garcia will happily take requests from the crowd, so if you've been practicing your rendition of "It's De-Lovely," here's your chance. 168 Ave B between 10th and 11th Sts (212-473-2830, boxcarlounge.com). Every other Mon 11pm; free.
Getting handsy on the dance floor is pretty much a given at this NC-17 bash. Nightlife fixture DJ Jess encourages grinding with a high-energy mix of electro, Britpop and house tunes, while drag queens and burlesque dancers circulate through the crowd in their hottest attire. The later you get there, the more raucous the vibe, so plan accordingly. The Studio at Webster Hall, 125 E 11th St between Third and Fourth Aves (212-353-1600, websterhall.com). Fri 10pm; $10.
This tiki bar and lounge cultivates an eclectic vibe with offbeat programming and live music almost every night of the week. Most sets kick off around 10pm, but that's just the first act. Depending on what time you roll in, you might catch a Mexican rock band or a Brooklyn punk group—it's best to just go with the flow. 538 14th St between Aves A and B (212-228-2240, ottosshrunkenhead.com). Schedule varies.