Krusty has a crisis of conscience and retires from show business after his father dies before ever approving of his career. Meanwhile, Lisa becomes worried about Homer's health and life expectancy.
Homer and Bart turn to the open seas to improve their relationship, and Marge becomes a trash talking victim after she drafts Homer's fantasy football team.
Marge opens a sandwich franchise store after her sandwiches become a huge hit at Springfield Elementary. But running day-to-day at the store proves challenging, especially when the same franchise opens another location across the street.
The 25th annual 'Simpsons' Halloween special includes an alternate dimension, a "Clockwork Orange"-style gang led by Moe and a visit from the Tracey Ullman-era Simpsons.
Bart tricks his family into a camping trip at a strange event known as "Blazing Guy" so that he can get revenge on his sadistic new fourth grade teacher.
Homer forms a cover band with other dads in town when he takes up bass guitar to deal with a mid-life crisis, but the band's modest success is soon overwhelmed by Apu's breakout potential.
Homer is hypnotized into believing he's ten years old and ends up stuck in his new age when the hypnotist dies, so he bonds with Bart and refuses to take back the responsibilities of adulthood.
Inventor Elon Musk comes to Springfield, and Homer inspires him with a new idea that could revolutionize Springfield, but winds up costing Mr. Burns a ton of money.
Marge gets a job as a driver for a transportation app service, while Moe is forced to work as a janitor at the nuclear plant after Homer causes the bar to go bankrupt.
The congregation, led by Marge, is forced to resort to gambling in order to collect money to fix the church, which Chief Wiggum destroyed with a jet pack he received by mistake.
After "Duffman" retires, Homer wins a reality competition to become his replacement. But his contract states that he cannot drink beer, which gives him a new perspective on alcohol.
Marge decides to follow Bart everywhere until he confesses to being involved in a bulldozer crash. Meanwhile, Homer ignores Santa's Little Helper when Ned gets a new dog.