Gary's parents receive the paper when Gary is trapped in an absndoned theater trying to save a monkey. Gary's parents and Crumb accidentally bring together a family of Letonian trapeze artists in Chicago.

Gary helps Renee, a woman who is being targeted by thieves.

To his surprise, Gary runs into his mother in the middle of Chicago. Later he shadows her and sees her drinking champagne with a strange man. Gary first suspects an affair, but learns that the stranger has tricked her into investing in a fictive company.

While Gary is able to prevent a robbery attempt by the dangerous criminals, he is unable to convince the local sheriff that the convicts are hiding out in his little town. It turns out that Joe is an envious old high-school classmate of Gary's who decides to throw him in jail for causing a raucous. While behind bars, Gary reads in the paper that his mother will be killed by the convicts. When he's unable to convince Joe to stop by his parents house to prevent the impending tragedy, Gary's dad, Bernie, comes to his rescue and they both rush to save Gary's mom.

Gary finds out why he was chosen to receive the paper.

A young Irish woman loses her chance at a million dollar lottery when Gary swipes her dollar that she was going to buy the winning ticket with. To repay her he ends up caught up in a wild scheme that has them pretending to be engaged while Kate looks for a man she loves.