If you're really into cocktails, don't miss Bemelmans at the Carlyle. It's got old-NY charm (it's covered in murals done in the late '40s by, yes, you guessed it, a guy named Bemelman) but the real reason to go are the drinks - the head bartender, Audrey Saunders, is great. (She got her start at The Rainbow Room with Dale DeGroff - see CDH's comment.) She's brought back a number of old world classics and the drink menu is a bit like taking a walk through mixology history. (There are drinks from the late 1800s for god's sake!) She also uses great ingredients - juices are fresh squeezed and she makes her own ginger beer in-house. The Gin Gin Mule is my favorite. If you go during the week, it's more casual - you could get away with jeans but likely not sneakers. The drinks are NOT cheap - in the high teens if I remember correctly - and there's a cover for the music, which starts at 5:30. But, if you have a passion for cocktails (as I do - can you tell?), you should make a pilgrimage if you can - lunch or late afternoon would be a good time to go. I also second the King Cole - another classic venue with great cocktails. I agree with CDH that many places made famous for their cocktails quickly lose their motivation. I find the other old-NY bars to be overrated - the Oak Room at the Algonquin and the Oak Room at the Plaza are charming but the drinks are, well, in my opinion, generally not very good. Let us know where you end up . . .