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- OverviewSep 26, 1999-May 21, 200022 episodesEpisodes22. Behind the Laughter May 21, 2000
- A "Behind the Music" style look at the Simpsons' life story.
- 21. It's a Mad, Mad, Mad, Mad Marge May 14, 2000
- A young woman temporarily moves in with the family, and Marge is charged with insanity.
- 20. Last Tap Dance in Springfield May 7, 2000
- Lisa outshines her dance-school teacher, a former child-star.
- 19. Kill the Alligator and Run Apr 30, 2000
- Homer gets caught up in spring break chaos while vacationing in Florida.
- 18. Days of Wine and D'Oh'ses Apr 9, 2000
- Forswearing alcohol, newly sober Barney spearheads a rescue mission to save Bart and Lisa.
- 17. Bart to the Future Mar 19, 2000
- A casino owner shows Bart the future, with Lisa as President of the United States.
- 16. Pygmoelian Feb 27, 2000
- Plastic surgery transforms Moe into a ladies' man.
- 15. Missionary: Impossible Feb 20, 2000
- Homer is forced to become a missionary on a remote island.
- 14. Alone Again, Natura-Diddily Feb 13, 2000
- When someone passes away, the Simpsons console a grieving friend.
- 13. Saddlesore Galactica Feb 6, 2000
- Bart and Homer rescue a horse and train it to race in a derby.
- 12. The Mansion Family Jan 23, 2000
- Homer plays billionaire while house-sitting for Mr. Burns, who has checked into the Mayo Clinic.
- 11. Faith Off Jan 16, 2000
- Bart teams with Brother Faith to help Homer when he gets his head stuck in a bucket of glue.
- 10. Little Big Mom Jan 9, 2000
- Lisa takes over the household after Marge is injured in a ski accident.
- 9. Grift of the Magi Dec 19, 1999
- A huge company takes over Springfield Elementary to use the children to develop the ultimate toy.
- 8. Take My Wife, Sleaze Nov 28, 1999
- When Homer forms a motorcycle gang with his friends, Marge is kidnapped by a rival gang.
- 7. Eight Misbehavin' Nov 21, 1999
- Apu's wife has octuplets.
- 6. Hello Gutter, Hello Fadder Nov 14, 1999
- Homer's perfect bowling game makes him a celebrity.
- 5. E-I-E-I-(Annoyed Grunt) Nov 7, 1999
- Homer and Bart cross tomato plants with tobacco plants and get a new addictive substance.
- 4. Treehouse of Horror X Oct 31, 1999
- Homer causes catastrophe at the plant; Bart and Lisa X-ray Halloween candy; the family murders Ned.
- 3. Guess Who's Coming to Criticize Dinner Oct 24, 1999
- Homer becomes food critic for The Springfield Shopper, and all the restaurants get good reviews.
- 2. Brother's Little Helper Oct 3, 1999
- Bart's personality changes when he's given drugs to fight attention-deficit disorder.
- 1. Beyond Blunderdome Sep 26, 1999
- Homer advises Mel Gibson about his new film, "Mr. Smith Goes to Washington."