Are you at a loss for somewhere to go have a good drink that is not a mob scene in Times Square? I know, that area is not my first choice to have a leisurely cocktail, but sometimes you are there and you need a good place to go. I suggest trying The Rum House. Located next to the Hotel Edison, this cozy little bar has a great neighborly feel to it with it's all wood accents and expertly crafted cocktails. Even if your spirit of choice is not rum, the bartenders will make a great drink for you.
The two best things about this place is first of all the rum selection. They have 30 plus rums to choose from and some fantastic reserve rums like El Dorado 21 year old and The Last of The British Navy Black Tot. Their rum based drinks are fantastic as well. I have had more than a few of their "Dark N Stormys" and "Tortugas."
The other great thing about this place is the live entertainment. They have live music every night of the week. It's so much fun to walk into this place and hear someone playing rag-time style songs on the old upright piano. I have even witnessed a a sing-along or two. So much better than the ambient bass heavy music you hear everywhere these days.
The crowd is always friendly, a good mix of locals and tourists, the bartenders are helpful. Times Square may not be your first choice for a bar destination, but the next time you are in that area of the city, I suggest The Rum House as the place for a nightcap.