The story follows Jack Hayward, a burly, guitar-picking philosopher from the Northwoods, who plans to revisit his college memories in Madison.
Just outside of town, he stops at the Rich Grounds coffee shop, where he immediately clashes with shop owner, Ricky Bonus. Ricky is a practical-minded bean counter, the anti-philosopher who doesn't go in for any touchy-feely stuff.
The locals persuade Ricky to put on an open mic, nominating Jack as their M.C. When Ricky's cheapskate store policies get him in hot water with a brash co-ed activist, the political nuts come out of the woodwork.
Meanwhile, Ricky's effervescent wife Angela gets swept off her feet by Matt Pleasant, a disciple of the latest positive-thinking craze. Throw in a creepy corporate spy who tries to trick Ricky into a lawsuit, and the madness is complete!