If you actually at a decent place, updscale bar, hotel bar, lounge, etc. go try a
Manhattan. I maintain that this is, and always has been, a classic man's drink but at a lot of places with sub-par bartenders it's way too sweet and completely chick. When well made, this is a damn fine drink and one of my personal favorites.
The sweet vermouth cuts the harshness of the rye and gives the drink a nice sweet tang, and the bitters give a subtle complexity to the drink. The bitters, which is the ingredient a lot of crappy bartenders leave out to make it a sickly sweet drink, add some complexity. To avoid the "chick drink" treatment, request it in a highball or old-fashioned glass, over the rocks if you feel like it.
And for real geekery, have a read though "Bartender" a seinen manga about a genius bartender solving people's problems. It's so silly but it's actually quite awesome, fun reading for dorky liquor connoisseurs
Bartender Manga - Read Bartender manga scans online.