The Best Episodes Directed by Rob Oliver
#1 - Holidays of Future Passed
The Simpsons Season 23 - Episode 9
In this futuristic holiday episode, Bart is a deadbeat dad living in Springfield Elementary (which is now an apartment complex instead of a school) with Principal Skinner as his landlord. Meanwhile, a pregnant Maggie goes into labor during a family dinner.
#2 - Barthood
The Simpsons Season 27 - Episode 9
Bart’s coming of age story a la “Boyhood” chronicles his life from six years old to his time as an accomplished young man. Along the way, his tense relationship with Homer, an overly uncaring version of himself, and Lisa, who overshadows him in every way possible, shape Bart more than he realizes.
#4 - Rednecks and Broomsticks
The Simpsons Season 21 - Episode 7
After getting lost in a game of hide-and-seek, Lisa wanders into the field and discovers three teenage girls who are practising Wiccans. Though she is sceptical of their spells, the girls assure Lisa that they never hurt anyone and ask her to join their coven. Just before Lisa is inducted into their pact, Chief Wiggum arrives and arrests the three girls for witchcraft and Lisa becomes the star witness in the trial.
#6 - Treehouse of Horror XXIV
The Simpsons Season 25 - Episode 2
In "Oh The Places You'll D'oh," the first of three spine-tingling stories, Homer rides around Springfield wreaking havoc as "The Fat in The Hat" in a rhyming Dr. Seuss-ian tale. In "Dead and Shoulders," Bart is beheaded during a kite accident, his head is attached to Lisa's body and they must live together as one. The final terrifying tale, "Freaks no Geeks," features Mr. Burns' traveling circus, The Burnsum and Bailey Circus, which has stopped in Springfieldland in the 1930s. Trapeze artist Marge and Strong Man Homer are performers and things go awry when circus freak Moe starts to make advances towards Marge.
#7 - Adventures in Baby-Getting
The Simpsons Season 24 - Episode 3
When Marge's car falls into a sink hole, she buys the perfect replacement to fit her family of five. But she quickly grows to hate it because, as she tells a shocked Homer, the car would be too small if she wanted to have another baby. Meanwhile, Bart and his friends are determined to find out what secret Lisa is keeping when Bart finds her cryptic messages and follows her sneaking off downtown for covert meetings after school.
#12 - The Boys of Bummer
The Simpsons Season 18 - Episode 18
Bart becomes a hometown hero when he makes the game-winning catch at his Little League game, sending the Springfield Isotots to the championship for the very first time. Meanwhile, Homer runs into some luck, when a customer misunderstands Homer's excuses for a sales pitch after falling asleep in a department store's display bed. The impressed store owner hires Homer as a salesman.
#13 - Kamp Krustier
The Simpsons Season 28 - Episode 16
When Bart and Lisa return home abruptly after a traumatic incident at Kamp Krustier, they put an end to Homer and Marge's romantic encounters. Without sex to distract him, Homer becomes a more productive worker and caring husband, but Marge misses the old Homer. Then, Bart and Lisa return to camp to confront the source of their trauma.
#14 - The Burns Cage
The Simpsons Season 27 - Episode 17
When Smithers is devastated by Burns’ lack of affection towards him, Homer makes it his mission to find him a boyfriend. Meanwhile, after Bart orchestrates the removal of the lead in the school’s stage production of “Casablanca,” Milhouse serves as a terrible understudy, which frustrates his co-star, Lisa.
#15 - The Nightmare After Krustmas
The Simpsons Season 28 - Episode 10
Krusty tries to impress his daughter as they spend Christmas with the Simpsons. Meanwhile, Reverend Lovejoy seeks converts after church attendance plummets, and Maggie is haunted by a spooky Christmas toy.
#18 - My Way or the Highway to Heaven
The Simpsons Season 30 - Episode 3
God and St. Peter contemplate what merits a soul getting into heaven, while citizens of Springfield remember their divine encounters.
#19 - The Serfsons
The Simpsons Season 29 - Episode 1
In a magical medieval world, Marge's mother is turned into an Ice Walker and the only way for Homer to afford the cure is to force Lisa to use illegal magic. When the King discovers this, he kidnaps Lisa, and Homer must lead a feudal uprising to save her.