Good cuban restaurant & music maybe?
I back the Esperanto suggestion 100% - Get the Tuna, that's easily the best entree on the menu. Overall, i don't think the food is that great at Esperanto but the vibe, the drinks and the price make up for it. It's always a good time.
I haven't been to Cafe Cortadito in a while (i guess since they raised their prices?) but my first two experiences there were nothing short of excellent. loved both their fried skirt steak and grilled skirt steak.
Boca Chica and Habana are obviously two other go-to's as well...
here's my personal food rundown from cafe cordtadito in case you wind up going there: http://www.immaculateinfatuation.com/...
I went to Boca Chica once. Found the food unremarkable, but worse was the fact that it was one of the loudest rooms I've been in and couldn't have a conversation.
Some of the appetizers at Esperanto are outstanding, especially the crab in banana leaf. I don't see the shrimp & potato cakes on the current menupages menu. Agree that the tuna is a good choice, but so is the carne asada. & great Mojitos.
Esperanto on C & 9th has a Cuban & Brazilian menu and often live Cuban or Brazilian music. They're actually quite good, and a fun place. You could call to find out about music schedule.
Cafecito, a little further north on C, is very casual, very good and very cheap, but I don't think they ever have music.
I was not impressed by Cafe Cortadito, and they raised their prices seriously after some good reviews. The food at Havana Alma de Cuba in the West Village is uneven, but they have music Thursdays through Saturdays.
re: Peter Cherches
I don't think Cafecito is that great. I went back there recently. I'd call them pretty good. I ordered skirt steak medium rare, they brought it medium well, and I had to persuade them to redo it, with the following dialogue (close paraphrase, probably not exact quotes):
"Is everything alright?"
"Well, I asked for that medium rare. That's cooked through."
"It's so thin, that's why."
"That's why they have to cook it for less time."
"Do you want to send it back?"
"Yes, I really do."
They were ultimately willing to redo it, but not before trying to persuade me that it was reasonable that they had overcooked it. And they redid it medium, not medium rare. It was fine, but not really quite how I ordered it. I actually liked the ceviche this time (years ago, when I last went there, it was too fishy). Everything was fine, just not outstanding. We also enjoyed the sangria.