Highly recommend Cask and Ale in Madison — great bourbon and craft beer bar
Bogey knows how to find me if he wants the full-fledged Madison drinking tour 
Can I get a Top 5?
Buck:
Here goes, with a few caveats: I won't list any of the many (in several cases, very good) local breweries with tap rooms and/or brewpubs in town (a bunch have sprouted up in recent years); I won't list some of the chains with solid tap lists (HopCat, Mr. Brews etc.); nor are these necessarily my personal favorites of where I spend time drinking (although -- some are). Rather, these are in my view the best independent taverns/restaurants with deep, thoughtful, and/or interesting beers on tap or available (and this list is beer-centric, without regard for other cocktails or wine or ...). (Having said that, there are literally dozens of places with solid beer lists these days in Madison -- Cask and Ale certainly among them).
In reverse order:
5) Waypoint Public House. OK, I lied; part of a mini-chain of three "public houses" in the Madison area, this one is about 200 yards from my house in the bedroom suburb of Monona. Deep and interesting list on tap; they always have solid choices from the West Coast, plus the locals. Decent food; good views of our famous Beltline from the outdoor dining/drinking patio.
4) Side Door Grill & Tap: Unheralded place that few talk about in beer circles, but they always have at least two or three surprising choices on tap. A very good rotating list. Just off State Street, beneath the popular Samba Brazilian Steakhouse. You literally enter through a side door off the side street; if you go, make sure to order the tater tots -- seriously.
3) Dexter's: A classic East Side Madison joint, once a sports bar w/ lots of TV screens that got bought out by some guys who know beer and food; maybe the best fish fry in town, which is saying something, given the competition. Always pouring stuff I've never heard of; a mix of old reliable breweries and adventurous stuff.
2) Cooper's Tavern: On the Capitol Square, and more of a restaurant (and well worth it for a solid meal), but -- man -- what a beer list. Maybe the deepest Belgiums in the area (much of it bottled, but some always on tap). A lot of old reliable stuff on tap, but it's pretty deep, and it has a truly terrific bottle list.
1) The Malt House. Maybe the best pure drinking tavern in town; no food, located on one of the busiest streets in Madison, kitty corner from the local porn shop. Not the deepest tap list in town, but a very good one, and the bottle selection is just great. Incredible variety of glasses from which to drink -- they match the beer w/ the stemware. Bartenders know their beer here, and easily -- as an added bonus -- the best single malt place in town. Absinthe to boot, and frequently live music.
Addendum: Having said all of that, the single best place for drinking in Madison -- this time of year -- is the Memorial Union Terrace on the UW-Madison campus, our own little bit of nirvana. I'll be there Saturday night.
