You should try Bryant's Cocktail Lounge, a venerable institution where the Pink Squirrel was invented:
The history of the Pink Squirrel ice cream drink, invented in Milwaukee
Most of us transplants are amazed by the devotion to Brandy. I was at a well-known supper club near the Dells (Ishnala) with a friend, and she asked me to fetch her a Manhattan. Then she said "WAIT, make sure it is a whiskey Manhattan, not brandy." I rolled my eyes and said, "sure thing." I went to the bar and just ordered a Manhattan, and the barkeep asked "Brandy or whiskey?" Okay, she was right.
Where is that Bloody from? Sobelman's? Wicked Hop?