The Roosevelt has all of the qualities of your friendly neighborhood bar with a touch of class without paying the price. The diversity of the crowd that regularly visits Matt's bar is diverse from dowtown hipster kids to lawyers to your average working joe. It's sophisticated but NOT snobby, which I think why it has such a broad appeal.
If you like beer, there is an endless variety and I guarantee you will like at least one. (If you hate bitter beer, try the Chimay!) If you're still stuck on wine, by the glass it almost always stays under $10...even for an amazing Pinot. Friday nights are usually pretty packed, (especially First Fridays)but any other night of the week it's a perfect spot to chat with friends or get cozy on the couch with your love.
Oh and you would be silly not to try some of the food, especially the hot doughy pretzel or the grilled cheese and tomato soup.