In his new role as an executive, Tim prepares for a business trip to Minneapolis. When they arrive, Tim is recognized by the local clients as "The Pudding Boy." As a child, Tim acted in a pudding commercial that got heavy play in Minnesota, featuring a 10-year-old Tim delivering the tagline, "Oopsy-doopsy, I made a pudding woopsy." The Boss is worried that people won't take Tim seriously and arranges to fly in Marty, an otherwise reasonable employee who becomes unhinged on business trips. As Tim tries to smooth things over with the clients, Marty encourages increasingly reckless behavior. They drive around Minneapolis, open containers in hand, until a cop pulls them over. Marty encourages Tim to deliver the pudding catch-phrase, but it backfires. The cop thinks Tim is so drunk that he's soiled his pants.
After returning home from grocery shopping to find a group of homeless people camping out on their stoop, Tim and Amy decide it's time to move. They interview with the co-op board of a new apartment building, and Tim absolutely nails it. They're accepted as tenants, as long as they sign an agreement saying they won't reveal that a certain celebrity lives in the building. Later, Tim rides the elevator with Hugh Jackman and is not impressed. He works with another neighbor, Eddie the Mattress King, to get rid of the famous actor. He brings in the homeless people from his old stoop and instructs them to bother any celebrity they see. They recognize Eddie from his commercials and harass him into his apartment. Tim and Amy are brought in front of the co-op board for revealing the celebrity--not Hugh Jackman, but Eddie. Evicted, they return to their old place to find Tim's homeless friends living in it.