In proper reverse order:
#10 Black Widower (Apr 9, 1992 - Season 3)
Sideshow Bob gets paroled, and marries Selma. However, Bart suspects that Sideshow Bob has something else up his sleeve.
Funniest obscure moment: Bart's attempt to explain Bob's murder plot to Homer via a puppet show.
#9 Homer at the Bat (Feb 20, 1992 - Season 3)
Mr. Burns bets $1,000,000 that his company team can beat a competing plant's team. In order to do so, he replaced the regular company team with new security guard Roger Clemens, new janitor Wade Boggs, lunchroom cashier Ken Griffey Jr., and other new employees like Steve Sax, Don Mattingly, Ozzie Smith, Darryl Strawberry, Jose Canseco, and Mike Scoscia (who runs the solid contaminate encapsulator).
Funniest obscure moment: Homer steps to the plate, and it's a homer for Homer. (The ball sails past the fence to a picnic area, striking a man on his head as he is about to eat a sandwich.) Homer taunts the losing team as he circles the bases: "Ha ha, cops can't win!'' "Get his licence and registration,'' orders Chief Wiggum.
#8 Bart the Daredevil (Dec 6, 1990 - Season 2)
The scene in which Homer accidentally attempts to skateboard across Springfield Gorge and doesn't make it is pretty funny, but even funnier is when he's loaded into an ambulance, which then hits a tree, sending Homer back over the cliff while strapped to a gurney.
Funny obscure moment: See above! Not only funny, but hideously/hilariously violent too.
#7 Homer and Apu (Feb 10, 1994 - Season 5)
After getting food poisoning from eating the Kwik-E-Mart food, Homer gets Apu, the Kwik-E-Mart employee, fired. Regretting his actions, Homer vows to get Apu his job back. James Woods guest stars.
Funniest obscure moment: Barney approaches some giant woman-shaped bottles of syrup. "Excuse me, ma'am," he asks, "Where are the lampshades?" When she doesn't answer, he rocks the bottle, "Ma'am?" It topples over, spilling syrup out of her head with a glugging noise. "Oh, I've killed her!" Barney laments, "It's all happening again!" He runs off crying, straight into a stack of cranberry juice bottles.
#6 Bart vs. Australia (Feb 19, 1995 - Season 6)
The government of Australia isn't impressed with Bart's prank phone call and demand that he apologies in person.
Funniest obscure moment: At the US embassy, the family walk inside the wrought-iron gates. Homer spots a marine standing guard: "Hey! Are you like one of those English guards who can't laugh or smile or anything? *makes noises and faces at him and gets a haymaker of a punch in the face* "OWWW!" Marine: "No, sir! United States Marine Corps, sir!"
#5 Radioactive Man (Sep 24, 1995 - Season 7)
Friendships could be torn when Bart and Milhouse are both up for the role of 'Fallout Boy' in the new "Radioactive Man" movie. Meanwhile, the town of Springfield sees $$$ and milk the "Radioactive Man" film crew for all their cash. Guest star Mickey Rooney.
Funniest obscure moment: At school, Principal Skinner makes an announcement: "Students, I have an announcement. One of your favorite comic book heroes, Radio Man --" Nelson: "Radio _active_ Man, stupid!" Skinner: "Strange, I shouldn't have been able to hear that. Anyway, ..."
#4 Homer Goes To College (Oct 14, 1993 - Season 5)
In order to continue in his job at the Nuclear power plant, Homer must attend college. Written by Conan O'Brien.
Funniest obscure moment: The inspectors want to test Homer's competence next, but Smithers apologizes for him, saying, "He couldn't _bee_ here." Burns fobs them off with some excuse about Homer chairing a conference on nuclear fission in Geneva. Unfortunately, Homer jumps up through a manhole cover just then, screaming, "The bee bit my bottom! Now my bottom's big!"
#3 Whacking Day (Apr 29, 1993 - Season 4)
While the town of Springfield prepares for the annual snake whacking day (which Lisa dreads), Bart gets expelled from school for embarrassing Mr. Skinner during a school inspection. Barry White guest stars.
Funniest obscure moment: Superintendent Chalmers inspects the school sandbox: "Excellent. Not a trace of urine."
#2 Mr. Plow (Nov 19, 1992 - Season 4)
After Homer wrecks the two family cars during a snowstorm, he buys a snowplow, and starts up Mr. Plow. However, the competition becomes cut-throat when Homer's best buddy, Barney, starts up a competing plowing business, Plow King. Guest stars Linda Ronstadt and Adam West.
Funniest obscure moment: Bart asks during the taped commercial, "You *are* fully bonded and licensed by the city, aren't you, Mr. Plow?'' Homer answers out of the corner of his mouth, "Shut up, boy.''
#1 Marge vs. the Monorail (Jan 14, 1993 - Season 4)
After getting $3 million from a fine due to Mr. Burns' illegal disposal of nuclear waste, the town decides to spend money on a needless monorail... built from shoddy materials. Leonard Nimoy guest voices as himself. Conan O'Brien written.
Funniest obscure moment: At the Lanley Institute Of Monorail Conducting, the lesson concludes: "MONO = ONE, RAIL = RAIL".
--
There you have it, my official top ten list. Hope you enjoyed reading it as much as I enjoyed remembering that time of hilarity, simplicity and innocence in our lives. Many thanks to The Simpsons Archive, the one-stop shop for all things Simpsons-related.
#10 Black Widower (Apr 9, 1992 - Season 3)
Sideshow Bob gets paroled, and marries Selma. However, Bart suspects that Sideshow Bob has something else up his sleeve.
Funniest obscure moment: Bart's attempt to explain Bob's murder plot to Homer via a puppet show.
#9 Homer at the Bat (Feb 20, 1992 - Season 3)
Mr. Burns bets $1,000,000 that his company team can beat a competing plant's team. In order to do so, he replaced the regular company team with new security guard Roger Clemens, new janitor Wade Boggs, lunchroom cashier Ken Griffey Jr., and other new employees like Steve Sax, Don Mattingly, Ozzie Smith, Darryl Strawberry, Jose Canseco, and Mike Scoscia (who runs the solid contaminate encapsulator).
Funniest obscure moment: Homer steps to the plate, and it's a homer for Homer. (The ball sails past the fence to a picnic area, striking a man on his head as he is about to eat a sandwich.) Homer taunts the losing team as he circles the bases: "Ha ha, cops can't win!'' "Get his licence and registration,'' orders Chief Wiggum.
#8 Bart the Daredevil (Dec 6, 1990 - Season 2)
The scene in which Homer accidentally attempts to skateboard across Springfield Gorge and doesn't make it is pretty funny, but even funnier is when he's loaded into an ambulance, which then hits a tree, sending Homer back over the cliff while strapped to a gurney.
Funny obscure moment: See above! Not only funny, but hideously/hilariously violent too.
#7 Homer and Apu (Feb 10, 1994 - Season 5)
After getting food poisoning from eating the Kwik-E-Mart food, Homer gets Apu, the Kwik-E-Mart employee, fired. Regretting his actions, Homer vows to get Apu his job back. James Woods guest stars.
Funniest obscure moment: Barney approaches some giant woman-shaped bottles of syrup. "Excuse me, ma'am," he asks, "Where are the lampshades?" When she doesn't answer, he rocks the bottle, "Ma'am?" It topples over, spilling syrup out of her head with a glugging noise. "Oh, I've killed her!" Barney laments, "It's all happening again!" He runs off crying, straight into a stack of cranberry juice bottles.
#6 Bart vs. Australia (Feb 19, 1995 - Season 6)
The government of Australia isn't impressed with Bart's prank phone call and demand that he apologies in person.
Funniest obscure moment: At the US embassy, the family walk inside the wrought-iron gates. Homer spots a marine standing guard: "Hey! Are you like one of those English guards who can't laugh or smile or anything? *makes noises and faces at him and gets a haymaker of a punch in the face* "OWWW!" Marine: "No, sir! United States Marine Corps, sir!"
#5 Radioactive Man (Sep 24, 1995 - Season 7)
Friendships could be torn when Bart and Milhouse are both up for the role of 'Fallout Boy' in the new "Radioactive Man" movie. Meanwhile, the town of Springfield sees $$$ and milk the "Radioactive Man" film crew for all their cash. Guest star Mickey Rooney.
Funniest obscure moment: At school, Principal Skinner makes an announcement: "Students, I have an announcement. One of your favorite comic book heroes, Radio Man --" Nelson: "Radio _active_ Man, stupid!" Skinner: "Strange, I shouldn't have been able to hear that. Anyway, ..."
#4 Homer Goes To College (Oct 14, 1993 - Season 5)
In order to continue in his job at the Nuclear power plant, Homer must attend college. Written by Conan O'Brien.
Funniest obscure moment: The inspectors want to test Homer's competence next, but Smithers apologizes for him, saying, "He couldn't _bee_ here." Burns fobs them off with some excuse about Homer chairing a conference on nuclear fission in Geneva. Unfortunately, Homer jumps up through a manhole cover just then, screaming, "The bee bit my bottom! Now my bottom's big!"
#3 Whacking Day (Apr 29, 1993 - Season 4)
While the town of Springfield prepares for the annual snake whacking day (which Lisa dreads), Bart gets expelled from school for embarrassing Mr. Skinner during a school inspection. Barry White guest stars.
Funniest obscure moment: Superintendent Chalmers inspects the school sandbox: "Excellent. Not a trace of urine."
#2 Mr. Plow (Nov 19, 1992 - Season 4)
After Homer wrecks the two family cars during a snowstorm, he buys a snowplow, and starts up Mr. Plow. However, the competition becomes cut-throat when Homer's best buddy, Barney, starts up a competing plowing business, Plow King. Guest stars Linda Ronstadt and Adam West.
Funniest obscure moment: Bart asks during the taped commercial, "You *are* fully bonded and licensed by the city, aren't you, Mr. Plow?'' Homer answers out of the corner of his mouth, "Shut up, boy.''
#1 Marge vs. the Monorail (Jan 14, 1993 - Season 4)
After getting $3 million from a fine due to Mr. Burns' illegal disposal of nuclear waste, the town decides to spend money on a needless monorail... built from shoddy materials. Leonard Nimoy guest voices as himself. Conan O'Brien written.
Funniest obscure moment: At the Lanley Institute Of Monorail Conducting, the lesson concludes: "MONO = ONE, RAIL = RAIL".
--
There you have it, my official top ten list. Hope you enjoyed reading it as much as I enjoyed remembering that time of hilarity, simplicity and innocence in our lives. Many thanks to The Simpsons Archive, the one-stop shop for all things Simpsons-related.