Mr. Hill is a hilarious local comedian who does THE best impression of President Obama. You can catch his impression on YouTube during interviews with the local Milwaukee press.
1. This is August 15 and a few days on either side. When all the leases in the central city turn over at the same time, many students and other renters leave vast piles of unwanted belongings on the curb as they change apartments. These items are often taken home by others as the population garbage picks the piles. When someone asks where you got an item, you reply "Hippie Christmas."
2. Most leases in Madison, Wisconsin go from August 15th to August 14th of the following year. Many students are stuck in no man's land from noon on the 14th to noon on 15th while the owners are turning over the apartments. Some people camp out overnight guarding their earthly possessions. In the aftermath of this multiple-day circus plenty of rancid old pieces of furniture are left out on the curb for opportunistic hippies to snatch.
3. Whether it makes them hippies or not, many UW students wait for Hippie Christmas to furnish their new (but not very new) apartments. It costs a lot of money to furnish a place and college students are often strapped for cash. The trick is to find something that isn't drenched beyond repair. Many finds are quite salvageable.
Milwaukee-speak for clear soda, such as 7-Up or Sprite.
"Notsoberfest" takes place the last weekend of September, kicking off La Crosse's famous Oktoberfest celebration. People stand around in beer tents and down pitcher after pitcher of beer. Just about everyone there is "not sober".
Nickname for Portland because of all the rainfall it receives. Puddletown has made its way into popular PDX culture, as it's commonly affixed to names of businesses, sports teams, et al.