After being embarrassed by a drunken video of himself, Barney vows to sober up. Newly clean, he gets work as a helicopter pilot.

In this clip show episode, Homer is honored at a Friars' Club Roast. A number of characters show up to roast him, but the celebrating is interrupted by Kang and Kodos, who say that humanity will be judged based on Homer's experiences.

The Simpsons go on a late-night attic search after Bart and Lisa (who are freaked out over a horror movie Homer let them watch) begin hearing voices -- and find Marge's ex-prom date Artie Ziff, who's on the run for cheating the shareholders of his company.

At the power plant a movie is shown where the workers endorse outsourcing and Mr. Burns announces that he is closing the plant and moving the work to India. Homer is the only union employee left on the payroll and he is sent to India to train the replacement workers, when he succeeds beyond expectations, he is given total control of the plant and declares himself a god. Meanwhile, Selma & Patty take Bart and Lisa to their MacGyver convention. When they discover Richard Dean Anderson doesn’t like MacGyver and much as they do, they kidnap him in retaliation. Anderson escapes only to enjoy the thrill and he turns himself back in so that he can escape again. When it happens over and over again, soon Patty and Selma are the ones who need a means of escape.

When the rest of the family seems to lack Christmas spirit, Marge contacts Martha Clause (Martha Stewart).

The town is abuzz when Cheech and Chong announce a Springfield stop on their much-anticipated reunion tour. But when Cheech and Chong take the stage in front of their loyal fans, the jokes were just not the same for Chong, so Homer steps in and delivers all the punchlines by heart. Impressed, Cheech invites Homer to go on tour with him as new duo “Cheech and Chunk” while Chong forms a more progressive comedic team, “Teach and Chong,” with Principal Skinner.

While Homer is on tour, Marge attempts to help the neighborhood cat lady and change her hoarder ways, but turns into a hoarder herself in the process, and Homer realizes that life on the road is not all high times and slapstick humor

Krusty the Clown becomes depressed after getting fired from his television show for being unpopular with children. The Simpson family encourages him to make a comeback, suggesting that he seek help from an agent they met earlier at a television museum. This agent turns out to be Annie Dubinsky, who was Krusty's first agent and former girlfriend.

When the Retirement Castle and the V.A. Hospital can’t solve Grampa’s health issues, the Simpsons decide to take a family trip to Cuba to get him cheap medical care.

God and St. Peter contemplate what merits a soul getting into heaven, while citizens of Springfield remember their divine encounters.