The Top 30 Simpsons Episodes

The Simpsons is over 30 years old, a show that has lasted 29 seasons and has over 625 episodes at the time of writing. It is the longest-running animated series and it has had quite a journey from its start as a way for an old drunk who made humans out of his rabbit characters to pay off his gambling debts. Starting as a series of shorts on the Tracey Ullman Show, the series has seen many comedic talents work behind the scenes and allowed for other adult animated shows to follow in its footsteps. It was also a show that has satirized American culture, pop culture, politics, and thorny subjects like education and religion. As someone who grew up on The Simpsons, I will look back at some of the best episodes the show has to offer. Please note that nothing beyond season 9 makes this list and many personal favorites, like "Bart's Friend Falls in Love," "Camp Krusty," and "The Homer They Fall," failed to make the cut. Stark Raving Dad (S3, E1) The Simpsons was a phenomenon even in its early days, and one of its earliest coups was getting Michael Jackson as a guest star - even if Jackson was credited as John Jay Smith. Made as a loose parody of One Who Flew Over the Cuckoo's Nest, "Stark Raving Dad" sees Homer being sent to a mental asylum for the crime of wearing a pink shirt (as well as Bart screwing up Homer's sanity test). In the hospital, Homer befriends a big white guy who thinks he the King of Pop and brings him home after it is discovered that Homer is sane. In addition to Jackson's guest starring voice role, the most remembered part of the episode is when Bart and Michael sing "Happy Birthday Lisa," showing that, despite their rivalry, Bart does care for his sister. Michael’s rendition of "Ben" was also touching as he tries to comfort Homer when he is first sent to the crazy house (there are conflicting reports over whether or not Jackson's vocal tracks were used for his character's singing voice, as Jackson also required a sound-alike singer, Kipp Lennon, also record the songs). The best jokes revolve around Homer's mental state – particularly when the head psychiatrist finds out Bart is real and when Homer threatens his son whilst still in the hospital. Mr. Plow (S4, E9) “It’s Mr. Plow, that’s his name - that name again is Mr. Plow.” Homer’s venture into the snowplow business was one of his most successful enterprises. Homer falls into the business by accident after smashing up both his family cars, but after he encourages his friend Barney to give the business a shot, he creates a rival. “Mr. Plow” is one of those classic Simpsons moments, like the self-referential joke about the Simpsons appearing on TV - Homer’s explanation for why he was out at night (a joke that is often cut from the Channel 4 broadcast in the UK), and Adam West’s appearance at a motor show. There is a great blend of wordplay, verbal jokes, and visual gags. It is a memorable episode that is constantly funny and subverts the ending of Homer and Barney choosing to work together by God dicking them about. Last Exit to Springfield (S4, E17) "Last Exit to Springfield" is deservedly considered a classic Simpsons episode. It is an episode that interconnects its two plots where the family dentist says Lisa needs braces or her canine tooth will rip right through her eyeball. This news happens at the worst possible time because the Nuclear Power Plant cancels the dental plan, leading Homer becoming a union boss fighting to reinstall it. "The Last Exit to Springfield" is one of the most visually comedic episodes thanks to visual gags like the montage of Burns and Smithers running the power plant, when the town loses and regains its power supply, and Lisa's Yellow Submarine dream. The scene where Mr. Burns questions Smithers as to why the strikers were singing after turning off the town's power supply was animated and written to be like How the Grinch Stole Christmas. The episode also had great verbal gags, like when Homer thinks Mr. Burns is coming onto him, Homer mind-loop of "dental plan, Lisa needs braces," and the classic statement "hired goons." A couple of the jokes even had a real-world impact: the line "ice to see you" by the Arnold Schwarzenegger parody Rainier Wolfcastle was really said by the Austrian Oak during Batman and Robin and West Ham footballer Michail Antonio celebrated a goal just as Homer celebrated his victory. The moment when all the strikers singing "they have the plant we have the power" is heartwarming. Whacking Day (S4, E20) "Oh whacking day, oh whacking day, our hallowed snake skull cracking day." The fourth season episode "Whacking Day" was written by the legendary John Swartzwelder and won a Genesis Awards from the Humane Society of the United States: particularly impressive because Swartzwelder is politically very right-wing. "Whacking Day" tells two interconnecting stories. The first centers around Bart getting expelled from school after driving a tractor into Superintendent Chalmers' butt (in his first appearance on the show). This leads to Marge homeschooling the wayward child. The other is about the titular Whacking Day - an annual tradition that has been called distasteful and puerile by a panel of hillbillies - an event that sees the townspeople beat snakes to death. Due to Bart receiving one-on-one education he becomes a model student and discovers the real history of Whacking Day and, along with Lisa and Barry White, resolves to save the innocent reptiles. "Whacking Day" is an episode filled with classic Simpsons jokes, like Barry White's horrible realization of what Whacking Day really is, Homer's ninja skills, and, of course "I am evil Homer." My favorite was Grandpa Simpson's flashback to World War II as a German cabaret singer. Homer Goes to College (S5, E3) "Homer Goes to College" deliveries exactly what it promises - Homer going to university. After causing a nuclear meltdown in a training van that had no nuclear material Homer is forced to go to university or lose his job because he is dangerously unqualified. Thanks to Mr. Burns, Homer is admitted to Springfield University and the Simpson patriarch believes college is going to be like in the movies, such as School for Hard Knockers. Unfortunately for Homer, the students want to learn, Homer befriends a trio of nerds and the dean of students is actually a nice, young man. That doesn't stop Homer from trying. "Homer Goes to College" is a classic episode filled with jokes starting with the surprise nuclear inspection, Homer not taking his studies seriously, and the Simpsons kids missing a once-in-a-lifetime Itchy and Scratchy episode because of the nerds. One of the most famous jokes, where Homer misspelled smart, was actually a mistake by voice actor Dan Castellaneta and the showrunners decided to keep this accidental brilliance. Itchy & Scratchy Land (S6, E4) The show-within-a-show Itchy & Scratchy is an ultra-violent parody of Tom and Jerry and was a point of contention between The Simpsons' producers and the censors. This was particularly heated in the mid-90s when cartoons were restricted regarding anything involving death and violence, and Fox executives even asked The Simpsons' producers to cut or tone down the shorts. So the logical response was to make an episode based around the controversial characters. "Itchy & Scratchy Land" was a double whammy of a parody because the story was similar to Michael Crichton's Westworld and Jurassic Park, where everything at an advanced theme park that can go wrong does go wrong. The other half of the parody is of the Disney Corporation, where the episode takes jabs against Disney World, Disney characters, and Walt Disney and his alleged unsavory views. It was a constantly hilarious and surprisingly thrilling episode. People who have ever been to Disney World in Florida can easily relate to this episode. Treehouse of Horror V (S6, E6) There are many great Treehouse of Horror episodes that could have made it onto this list but arguably the best is "Treehouse of Horror V," the sixth season's version of the tradition. This was the first Halloween episode where the showrunners dispensed with the framing device and just focused on making three very funny shorts. "Treehouse of Horror V" has three of the best Halloween shorts that the show has to offer - "The Shinning" that was such a spot on parody of Stanley Kubrick's The Shining that you cannot watch the film without thinking of The Simpsons, "Time and Punishment" where Homer ends up messing with the fabric of time, and "Nightmare Cafeteria" which sees Bart and Lisa survive when the school becomes a haven for cannibalistic teachers. All three are so funny that it is hard to pick a favorite. All three are connected by a running gag where Groundskeeper Willie gets axed in the back when trying to save The Simpsons: as he states, he is bad at this. Lisa on Ice (S6, E8) I have a soft spot for sports episodes and the hockey-themed episode "Lisa on Ice" is one of the best The Simpsons has to offer. After being publically shamed for failing gym, Lisa has to join a junior sports team and discovers that she has a talent for hockey: but this puts her in direct competition with her brother as the family jock. "Lisa on Ice" is a story about sibling rivalry and how it can affect a family. Bart and Lisa lived in the shadow of the other in their respective fields: so it is a big change when Lisa finds she is good at a sport. It even leads to Bart trying and failing to become family brainiac leading to hilarious consequences. The episode has a touching ending when Bart and Lisa face-off against each other and they think of all the good acts they did for each other and skate off together whilst the residents of Springfield riot. The episode also has many great jokes like the Ralphism "me fail English thats unpossible," finding out the name of the school auditorium, and wordplay like "It's a lucky coincidence you happen to be your sister's brother!" There are too many to list. The episode's cultural impact was secured by making fun of the Apple Newton and I can relate all too well to Uter's dilemma. And Maggie Makes it Three (S6, E13) Episodes showing the Simpson children, Homer, and Marge in their younger days are often some of the show's best episodes. Episodes like “The Way We Was,” “I Married Marge,” “Lisa’s First Word,” and “Lisa’s Sax” are all worthy to be placed on this list. However, it’s “And Maggie Make it Three” which makes the cut. As the title suggests, the episode focuses on the time just before Maggie was born. Homer finally gets out of debt, so he quits his job at the Nuclear Power Plant to take on his dream job as a pin monkey at the Bowling Alley. The family is financially secure as a unit of four. However, this security is put in jeopardy with Marge pregnant for the third time. “And Maggie Make it Three” is an episode with classic Simpsons moments, like Homer’s ninja fantasy, Homer ripping out his hair every time Marge tells him she’s pregnant, and Homer hearing what he wants to hear when people congratulate him. Yet, what makes the episode so special is the dilemma Homer and Marge were put in - Marge did not want to tell Homer about her pregnancy because it would ruin Homer’s happiness whilst Homer knows he has to do right for his family. The episode shows that at his workstation is a plaque saying ‘Don’t forget you’re here forever’ yet Homer turned it something heart-warming by placing photos of Maggie on it and makes it say ‘Do it for her’. The PTA Disbands (S6, E21) One of the favorite topics of satire in The Simpsons is the American education system, particularly how underfunded it is. In the episode the teachers at Springfield Elementary go on strike after Principal Skinner’s penny pinching goes too far. The prolonged strike forces the residents of Springfield to take up the teaching posts since advance cyborgs haven’t been invented yet. The episode starts off with the hilarious field trip to a Civil War fort where the school bus is falling apart, the cannon pointed at a watchtower, and the Springfield students getting attacked for trying to learn for free. This sequence leads to the running gag of "What happened to Uter?" From there, Bart inflames the conflict between Skinner and Krabappel, forcing the strike to happen and then uses it to go wild whilst Lisa worries about her future and education. Bart gets to cause havoc at a construction site and Lisa breaks the laws of thermodynamics. The episode is littered with jokes like a parent panicking that the PTA was disbanding and Professor Frink teaching kindergarten. Audiences can come back to the episode and notice more subtle jokes like the book titles. The episode still has a cultural impact - Jasper’s phrase of "lots of padding" has become an annoying internet meme - whilst in 2004, The Scotsman quoted Homer when reporting about the Simpsons’ voice actors' strike. The Springfield Connection (S6, E23) "The Springfield Connection" has a simple premise: Marge becomes a cop and hilarity eschews. After helping capture Snake because of a crooked game of Three Card Monty, Marge ends up becoming an adrenaline junkie and seeks excitement by joining the Springfield Police Department. She quickly becomes the best officer in the department, but Homer tries to take advantage of Marge's new position and there is a criminal conspiracy surprisingly close to home. "The Springfield Connection" is an episode filled with many classic jokes like "you missed the baby, you missed the blind man" (American military training in a nutshell), and Homer waving his right to remain silent. Other jokes I didn't understand until I was older like Homer saying "John Williams must be rolling around in his grave." But that is the beauty of The Simpsons: you can come back to show when you're older and find something new. Who Shot Mr. Burns Pt. 1 and Pt. 2 (S6, E25 and S7, E1) “Who Shot Mr. Burns” was an event of a storyline - it was one of only two two-part episodes in The Simpsons history. It was also one of two series finale to end on a cliffhanger, the other being “The Ned-Liest Catch,” and it ended with an audience vote. In this two-parter, Mr. Burns is even more evil than usual and crosses many of Springfield's most famous resident. When Mr. Burns finds out Springfield Elementary has struck oil, he seeks out to usurp the new resource. His slanted oil drilling operation leads the school into a financial crisis, forces Moe to close his bar, makes the Springfield Retirement Castle fall into a sinkhole, and injuries Bart’s dog. When Smithers grows a backbone and stands up to Mr. Burns he gets fired for insubordination. And Homer is annoyed Mr. Burns doesn’t know his name despite working for and interacting with him for years. The first episode sets up all the pieces of the mystery whilst the second has some excitement when Homer gets arrested for the murder. “Who Shot Mr. Burns” was one of the most ambitious Simpsons stories and tickled the funny bone throughout, like when Moe was attached to a lie detector and a brilliant satire of Basic Instinct. The cliffhanger was so big that there was a live-action special hosted by America’s Most Wanted’s John Walsh about the suspects and Vegas was taking bets on who the shooter was. Radioactive Man (S7, E2) Radioactive Man is a popular superhero in The Simpsons universe and, like many comic book creations, he gets a film adaptation which was filmed in Springfield. It was a magnificent moment for the town which, naturally, they blew. The episode satirized superhero adaptations, with Radioactive Man being a surrogate for the 1950s Superman serials and the 1960s Batman series, and despite the episode airing in 1995 it works as a commentary about the superhero boom of the 2000s. In 22 minutes, the episode covers a lot of territory as it comments on Hollywood production and child stardom as everyone in the town is obsessed with making money from the production. "Radioactive Man" was a joke-filled episode that somehow predicted internet movie fandom through Comic Book Guy, taking a few jabs against Waterworld and has the classic line "My eyes, the goggles do nothing." Home Sweet Homediddly-Dum-Doodily (S7, E3) “Home Sweet Homediddly-Dum-Doodily” was slightly darker by Simpsons standards yet still heartwarming. In the episode, Bart, Lisa, and Maggie are placed into foster care after a series of misunderstandings and Homer and Marge have to prove they are good parents – although if The Simpsons was slightly realistic, Bart would be monitored considering how abusive Homer is to him. Child Services makes their actions even cruder by placing the Simpson children with the Flanders clan, leaving them 10 feet away from each other but not able to have any contact. The episode had a lot of dramatic moments, like Marge being told she would be arrested when trying to get past a social worker, and emotional moments, like when Marge and Homer read a headline written by the Bart and Lisa. There is also a sweet ending when Maggie looks like she was going to choose the Flanders over the Simpson but changes her mind when she sees her mother. “Home Sweet Homediddly-Dum-Doodily” does have its funny moments – my personal favorite being when Homer took a baptism for Bart. There was also a joke for die-hard fans when they showed a statue of John Swartzwelder outside Swartzwelder County Court – it was joked in the DVD commentary that there must have been some Gerrymandering in Springfield. Bart Sells His Soul (S7, E4) Religion is often a topic that The Simpsons addresses and one of their best-known episodes about the subject is "Bart Sells His Soul." The title describes the plot in a nutshell - Bart sells his soul to Milhouse for $5, thinking he has made the deal of the century. However, Bart is unable to laugh and has strange dreams leading to Bart thinking he may have sold Milhouse more than a piece of paper, leading to a difficult night on the streets of Springfield. At the same time Moe reinvents his business by turning his dank bar into a family restaurant: but Moe doesn't have the temperament to work with children. "Bart Sells His Soul" is one of the best episodes because of how emotional Bart's quest to retrieve his soul becomes for the young boy. It is also a funny episode with the most memorable material coming from the Moe storyline - particularly his patrons wanting to keep the bar as it is. One of the most famous jokes comes when Bart tricks the church into singing "In-A-Gadda-Da-Vida" by Iron Butterfly. The original plan was to use Led Zeppelin's "Stairway to Heaven" but it wasn't possible due to the rights being too expensive. This was a blessing in disguise because the lyrics from "In-A-Gadda-Da-Vida" fitted the church setting better and the song is 17 minutes long. Team Homer (S7, E12)   There are many sports episodes in The Simpsons canon: Bart and Lisa played hockey, Bart played football, and Homer got to play softball with professional MLB players. Another team Homer was a part of was the Pin Pals, forming it with Apu, Moe, and that long haired freak Otto. But Homer’s ambitions to win the league are put in jeopardy when Mr. Burns demands to join the team. Meanwhile, Springfield Elementary turns into a bland dystopia after Principal Skinner introduces school uniforms. “Team Homer” is an episode that had two satisfying plots that are as funny as each other. A favorite joke of mine is when Homer and his team return some beers to the bowling alley owner. The episode also continued the constant suffering that is Hans Moleman’s life. At the school the big jokes were when the Springfield Elementary students blink at the same time and the students go wild when the rain washes away the gray on uniforms. It’s a simple yet constantly funny episode Homer the Smithers (S7, E17) Smithers is unflinchingly loyal to Mr. Burns and a running gag throughout the show is his unrequited love for his boss. After Smithers fails to protect Mr. Burns from a drunken "lout," he falls into a depression and his boss demands his assistant take a vacation. To ensure his position is there when he returns, Smithers hires Homer as his replacement. “Homer the Smithers” is simply a hilarious episode from end-to-end, starting with the Simpsons’ visit to the Drag Racer and continuing from there. Some classic moments include Mr. Burns’ mace, Homer making Mr. Burns’ breakfast, the montage of Homer’s failures, and the fight between Homer and Smithers, which actually shows Smithers to be pretty tough. The most famous joke is Homer reading the messages about Mr. Burns’ car/cube – it still cracks me up. 22 Short Films About Springfield (S7, E21) "22 Short Films About Springfield" was an experimental episode from the seventh season that moved away from centering a story around the Simpson family and spread it evenly amongst the many residents of Springfield. The episode was really 20 short stories that flowed from one to other. Particular highlights were Smithers showing that, even when dying, he was taking orders from Mr. Burns, Skinner inviting Superintendent Chambers, and, best of all, a parody of Pulp Fiction involving Chief Wiggum, Snake, and Herman Hermann. The episode also marked the first appearance of the Very Tall Man, whose appearance was based on Ian Maxtone-Graham, who become a writer for the show, with the character giving Nelson his deserved comeuppance. Raging Abe Simpson and His Grumbling Grandson in "The Curse of the Flying Hellfish" (S7, E22) Abraham "Grandpa" Simpson is a grandfather that is constantly been ignored by his family, and for good reason, seeing he was an incredibly bad father to Homer. One of his biggest episodes is also the longest titled episode in Simpsons' history and it looked his war service which comes back to haunt him. In the episode Grandpa ends up being one of the last two surviving members of his platoon, the other being Mr. Burns. The last man standing would complete a tontine for a collection of stolen German paintings. Mr. Burns can't wait for time to get rid of Grandpa, so he hires an assassin to speed things up, leading to Grandpa and Bart to find the paintings. In this episode, Grandpa Simpson is even more curmudgeonly than usual - he starts the episode as a sullen figure who keeps telling outrageous stories. Yet he is shown to be quite a badass when the episode shows his war career - he nearly assassinated Hitler. Even in his old age, Grandpa is demanded and reliable, and the combination of his grandson's support and his personal quest give him a zest for life. The episode is an adventure and has exciting moments, like Grandpa chasing down Mr. Burns and Smithers. The funniest are the various failed assassination attempts and Grandpa and Bart requisitioning the Flanders' boat. The episode also includes Mr. Burns attempting one of his most evil acts within the show when he attempts to kill Bart by kicking him into a case and letting him sink to the bottom of the sea. Much Apu About Nothing (S7, E23) Immigration is a topic that The Simpsons has addressed and the first (and best episode) to tackle the issue is the season seven episode "Much Apu About Nothing" or, as it was originally titled, "The Anti-Immigrant Song." After the town of Springfield installs the bear patrol the townspeople suffer a tax raise and to duck the issue Mayor Quimby blames it on immigrants and plans to deport them if Proposition 24 is passed. This affects Apu Nashasapeemapetilon who stayed in America after his student visa expired: he would lose his home and livelihood, and would be made into a pariah. "Much Apu About Nothing" is an overtly political episode and it as timely today as it was back in 1996: perhaps even more so because of the man now in the White House. The episode highlights how immigrants are made into scapegoats and how quickly xenophobia can spread. The scene with Moe and his patrons' incoherent complaining about immigrants integrating into society pretty much sums up people with extreme views against immigration. The episode gave us the classic line "When will people learn, democracy doesn't work." A deleted scene showed the Arnold Schwarzenegger surrogate Rainier Wolfcastle making a campaign video supporting the anti-immigration proposition. It should have remained in the episode. Summer of 4 Ft. 2 (S7, E25) "Summer of 4 Ft. 2" was the seventh season finale and was inspired by showrunner Josh Weinstein's family vacations. After Springfield Elementary breaks up for the summer Lisa finds out she is unpopular and goes unnoticed. When Homer begrudgingly accepts Flanders' offer to stay at his neighbor's beach house Lisa sees this as an opportunity to shed her nerdy image and reinvent herself as a cool kid, usurping Bart's position. "Summer of 4 Ft. 2" is one of those episodes that combines an emotional and relatable story with great jokes. It is an episode that starts with Milhouse asking Bart about his favorite sprinklers and ends with Lisa finding out she has friends who like her for who she is. It's an episode that offers a positive message: be true to yourself. Homer and Milhouse offer the best jokes in the episode. Homer goes on a quest for illegal fireworks, which leads to the show copying a joke from American Graffiti and making it even funnier, whilst Milhouse develops his status as the show's punching bag. Treehouse of Horror VII (S8, E1) The Treehouse of Horror episodes are an excuse for The Simpsons to let their hair down and do whatever they want, leading to wacky adventures and movie/TV parodies. The three plots in the seventh Halloween surprise are Bart discovering he has a psychotic twin brother, Lisa accidentally creating a microscopic world, and the aliens Kang and Kodos replacing Bill Clinton and Bob Dole during the 1996 Presidential Election. "Citizen Kang" is my favorite because it has the funniest jokes, like a double whammy of Homer's willingness to give up his family to the aliens and then preparing to have an anal probe. The setting of the presidential election allowed for a lot of political humor: Bob Dole/Kodos gets to sum up American politics in 20 seconds. A band even named themselves after the quote "I voted for Kodos." The other two segments have their charms, like how Homer revealed the existence of Hugo and the mini people getting revenge against Bart. Hurricane Neddy (S8, E8) As the title suggests, “Hurricane Neddy” is an episode that focused everyone’s favorite Christian and explores his character. In the episode Springfield is struck by Hurricane Barbara: if you think naming a hurricane after a woman is sexist then you clearly haven’t seen the ladies at clearance sales. Despite the Flanders seemingly being prepared for the weather event, the family home is flattened and the family left broke, causing Ned to have a mental breakdown. “Hurricane Neddy” is a fine example of The Simpsons doing what it does best - combine great jokes and genuine emotions. This was an episode back when Ned was a more likable character, a decent, charitable man who believed in the positive virtues of the Bible and it is hard not to feel for him when his house is destroyed. The scene where he snaps at the townspeople is both hilarious and tragic. Other highlights during the episode include Ned committing himself to a mental hospital and the reappearance of Jay from The Critic and John Swartzwelder. The Simpsons crews' favorite moment was when Homer was used by a team of psychiatrists to get Ned mad. “Hurricane Neddy” ends with Ned promising to no longer bottle up anger and he is true to his word, like in the episode “Bart Star.” The Itchy & Scratchy & Poochie Show (S8, E14)   The show within a show Itchy & Scratchy often acts as an avenue for The Simpsons production team to satirize itself and comment on people who criticize the show. This was most evident with the season eight episode "The Itchy & Scratchy & Poochie Show" which was made as a response to critics saying The Simpsons was coming to an end and to Fox suggesting the show should introduce a new member to the Simpsons household - a move that worked so well for shows like The Brandy Bunch, The Partridge Family, and Gilmore Girls. The episode sees Itchy & Scratchy going through a ratings rut despite the fans still loving the show. To remedy this the showrunners create a new character, Poochie the Dog, a kung-fu hippie from Gangsta City. Homer ends up getting cast as the cartoon dog and he is downcast when the character flops, so does everything in his power to save him. "The Itchy & Scratchy & Poochie Show" is a fine commentary on The Simpsons' production and the fandom - one of the big scenes being Homer taking down Doug the Nerd regarding a logic hole in an Itchy & Scratchy episode. The writers and animators for Itchy & Scratchy were based on the personnel who worked on The Simpsons and the character of June Bellamy was a tribute to the prolific voice actress June Foray. As well as being a funny episode, "The Itchy & Scratchy & Poochie Show" offered a level of sincerity that is missing in the modern version of the show due to Homer's attachment to the Poochie character. Homer's Phobia (S8, E15) "Homer's Phobia" is a controversial episode that has divided public opinion. Some see it as a great step forward for LGBT representation in mainstream culture whilst other,s like Steve Williams and Ian Jones from Off the Telly, placed it as one of the worst Simpsons episodes in 2002. I personally found it to be a very funny episode. "Homer's Phobia" sees the Simpsons family befriend John (John Waters), the owner of a collectibles stores and invite him to their home: even Homer has a good time and plans to set the gentleman up on a date. But Homer is horrified to find out John's gay, and worries that Bart might become gay as well, so sets out to "man up" his son. The episode is arguably the first to introduce "Jerk-Ass Homer," a character who has already been known for strangling his son, has issues with alcohol, and is always up for a get-rich-quick scheme. But John takes Homer's abuse in his stride and keeps a good nature. I roared with laughter when I saw the gay steel mill scene and it still makes me smile. Brother From Another Series (S8, E16) This may surprise some people but "Brother From Another Series" is my favorite Sideshow Bob episode, beating his appearances in "Cape Feare" and "Sideshow Bob Roberts." This episode sees Sideshow Bob getting released from prison again after the recommendation of Reverend Lovejoy and being offered a job by his brother Cecil, played by David Hyde Pierce. Considering how many times Bob has tried to kill Bart, the plucky 10-year-old is skeptical that he has reformed - so Bart and Lisa investigate what Bob is up to. Kelsey Grammar and David Hyde Pierce were both starring in Frasier, the popular NBC sitcom, thus allowing "Brother From Another Series" to combine the best aspects of Frasier and The Simpsons. The episode had a great back-and-forth between Grammar and Pierce, showed how Bob Terwilliger became Sideshow Bob, and was a joke-laden episode. Some of my favorite moments were Bob's hooting, when Bob and Bart fall down the dam, and Cecil tricking Bob at the end of the episode. This episode would have been a perfect send-off for Sideshow Bob but the character was ruined in subsequence episodes. Grade School Confidential (S8, E19)   Seymour Skinner and Edna Krabappel are arguably two of the saddest characters in The Simpsons: an incredible feat considering the show has Moe Szyslak, Hans Moleman, and Comic Book Guy. Skinner is a traumatized Vietnam veteran who lives with an overbearing mother and Mrs. Krabappel is a lonely divorcée who is a glorified babysitter to a group of dead-eyed fourth graders. The episode "Grade School Confidential" gives the pair a chance for happiness after the pair hook up and start a relationship, using Bart as a cover with the promise of a good school record. However, their happiness is short-lived after their relationship is exposed to the town and they are fired from their jobs. The episode had a long-lasting impact on the show: Skinner and Krabappel were together for seven seasons until they nearly got married in "My Big Fat Geek Wedding." Even after their break up, Skinner tried to get back together with Krabappel until she married Ned Flanders. "Grade School Confidential" is a sweet episode as well as funny. Skinner and Krabappel had a touching moment when they danced together and it is hard not to feel sorry for Edna when she talks about her lonely lifestyle. The line between comedy and tragedy is blurred when Skinner reveals he is a 44-year-old virgin. Some of the funniest moments in the episode are when Skinner and Krabappel change Bart's permanent record, Krusty's reaction when Maude spells sex, and it has the great Ralphism about babies. Homer's Enemy (S8, E23) "Homer's Enemy" is a divisive episode, even among The Simpsons production staff, and is easily one of the darkest. The idea behind this episode is what would happen if a regular person came to live in Springfield and this was done through Frank Grimes - a man who had to work hard every day just to achieve everything he owns. So he is shocked to see that a glutinous man - who is dangerously unqualified - is somehow living the American Dream. A criticism leveled at the episode was that it is an example of "Jerk-Ass Homer," but he really is more unaware of his actions than taking them out of malice. Homer also tries to make amends with Grimes after the man says he hates him. It's a drama as much as a comedy because of moments like Grimes visiting the Simpson home. The scene where Grimes snaps is an example of black humor at its finest. The subplot involving Bart buying a factory offers some light relief, even if it does involve some child endangerment. The City of New York vs. Homer Simpson (S9, E1) "The City of New York vs. Homer Simpson" is a controversial Simpson episode but this was completely unintentional because it centered around the World Trade Center. After a night where Barney is forced to be a designated driver he goes missing for two months and leaves Homer's car in the middle of World Trade Center Plaza. This means the Simpsons get to go on a road trip to the Big Apple - a city Homer swore he would never return to after a bad experience in the '70s. With Homer having to wait by the car and fight his full bladder, the rest of the family gets to see the sights. They get to enjoy a Broadway show, Bart tries to swindle the users of the New York Subway, and Bart tells a boat of immigrants the country's full. Both parties experience different sides of the great city. The episode marks the first appearance of Duffman and also spawned a stupid conspiracy theory that The Simpsons predicted 9/11. Trash of the Titans (S9, E22) It is rare for a show to reach 200 episodes and even rarer to do so back in the late '90s. For their 200th episode, The Simpsons deserved a grand story, which they got. After Homer offends a couple of garbage men and Marge forges an apology by him, Homer decides to run for Sanitation Commissioner- running on a campaign based on unrealistic promises. But governing is even more difficult than campaigning. The episode has become surprisingly relevant because Homer's campaign has been compared to Donald Trump's - both made outlandish statements about what he can achieve in office and smeared his opponent. The parody is so in-depth that Homer has a simple campaign slogan, "Can't someone else do it?" and he claimed his opponent Ray Patterson (Steve Martin) lured children to his basement, much like how Hillary Clinton was falsely accused of running a pedophile ring from a pizza parlor. It does sum up the state of modern politics on the right and left in the US and the UK. Patterson even makes a statement that the public can vote for an experienced public servant or a madman promising them the world. In this case, the voters choose the latter. The episode also had an impact on left-wing politics after the Toronto City Council proposed turning a mine into a dump and New Democratic councilors Jack Layton and Olivia Chow showed the episode in a meeting. Layton even went on to become the leader of the New Democratic Party. The episode won an Emmy back in 1998 and was praised for having an environmental message. It is a hilarious offering, having moments like the parody of "The Candy Man," Homer getting beaten up by U2's security, and finding out there is always a line to register as a sex offender. "Trash of the Titans" had a touching tribute to Linda McCartney at the end. The episode also caused a minor controversy in the UK because of the use of the word "wanker."