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November 18, 2007 Slideshows » Culture, Arts & Entertainment

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The 20 Most Disappointing Simpsons Moments Ever 

The Simpsons is in the middle of a record 19th season, making it the longest-running American sitcom. And the show is still occasionally funny, from what we hear. But people need to pull their heads out of the ground and recognize that it isn't always that great. By Zach Oat.
20. Homer's Life Dissected (Homer's Enemy, May 4, 1997) While it was entertaining to watch new character Frank "Grimey" Grimes experience a mental meltdown as the high points of Homer's sitcom life (astronaut, country singer manager, etc.) were constantly rubbed in his face, viewers at home were forced to confront the sheer ridiculousness of the show.
19. Patty Officially gay (There's Something About Marrying, Feb. 20, 2005) We arent disappointed that Selma is gaywere just sad that the show felt it necessary to spell it out, rather than leave it as assumed, like they did with Waylon Smithers. Especially since they then dodged controversy by having Patty call off her same-sex wedding, when her partner turned out to be a dude.
18. The First Clip Show (So It's Come to This: A Simpsons Clip Show, Apr. 1, 1993) Barts practical joke on Homer leads to a practical joke on America when the hospital-bound family retells stories from the first five seasons. Seriously? A clip show? It would become an annual event, but it would be two years before they had the brilliant idea to have Troy McClure host it, taking some of the stink off.
17. Bart Shoots a bird (Bart the Mother, Sept. 27, 1998) In the beginning, it took a couple of years for The Simpsons to shake off the excess sentimentality and replace it with comedy gold. So when Bart accidentally killed a bird with a BB gun in this episode and takes her unhatched eggs as his responsibility, we all prepared for the backslide. Also: Hartmans final episode.
16. Shearer Says Show Stinks (August 10, 2004) Note to writers: when one of your stars says the show is awful, theres a problem. Despite making $250,000 an episode, Harry Shearer (the voice of Mr. Burns, Smithers and Flanders) says in an interview that the last three seasons are among the worst, and that watching old episodes makes him sad for the good ol days. Us, too, Harry.
15. Homer Hired by Baldwins (When You Dish Upon a Star, Nov. 8 1998) Homer has held some strange jobs, but none stranger than personal assistant to Alec Baldwin and Kim Basinger. If it seems odd to create a stunt-casting episode around two actors who werent terribly popular at the time, it was! Luckily, the episode also had Ron Howard in it. Phew!
14. The Simpsons Canonized (Simpsons Bible Stories, Apr. 4, 1999) Having the Simpsons gain super powers or stay at a haunted hotel in a Treehouse of Horror episode is one thing. Having them act out Bible stories (or tall tales, or historical biographies) is another. We get ittheyre dreaming. None of this is real. Now tell us the story of something thats actually happening.
13. Toy line cancelled (2004) Five years ago, Playmates Toys World of Springfield line was the Simpsons collection to have, with its massive cast of characters and dialogue-packed playsets. Sadly, sales of the line trickled off after Series 16right before we would have gotten Sideshow Bobs brother, Cecil Terwilliger. Curses!
12. Homer and Ned go to Vegas (Viva Ned Flanders, Jan. 10, 1999) The rivalry between Homer and neighbor Ned Flanders was always classic, so why not ruin it by sending them on a buddy trip to Sin City? Then, make them both look like terrible husbands by having them marry dirty tramps! Ned loses his saintly character, and Homer loses a foe.
11. Snowball II Forgotten (I, Doh-bot, Jan. 11, 2004) Sure, he was a replacement cat, but Snowball II was a loyal pet to the Simpson family for years. So why was his death (as well as those of Snowballs III and IV) swept under the rug as if nothing happened? They even renamed Snowball V Snowball II so the episodes could air in any order and no one would be the wiser. For shame.
10. Marge in Maxim (April 2004) This was a disappointment in two ways. For Maxim fans, it was a disappointment because Marge is a cartoon character and not an actual woman. And it was a disappointment for Marge fans because she wore her regular dress through the entire photo shoot. Show some yellow skin, for Petes sake!
9. Grampa Dates Selma (Rome-Old and Juli-Eh, Mar. 11, 2007) Grampa Simpson hasnt been with a lot of women: Homers mother, the lady who died and left him all that money, Jasper that one timeand Marges mother, Jacqueline Bouvier. So isnt it just a little bit strange that now, 13 seasons later, he would strike up a relationship with her daughter, Selma? Shameless.
8. Homer the Prank Monkey (Homer vs. Dignity, Nov. 26, 2000) Remember on Seinfeld when George Costanza pitched a TV show about a guy who was sentenced to be Jerrys butler? Well, even that show was funnier than this episode, where Homer was forced to be Mr. Burns prank monkey in order to get a raise. Cartoon characters playing pranks on each other? Somehow less funny.
7. Movie Doesnt Get Made (1995) Despite having dropped hints about it repeatedly, and indicating that it was on the horizon, series creator Matt Groening starts saying that there will probably never be a Simpsons moviethat theyve missed their window, that the deal is too complicated, etc. Fans enjoying a quality TV show weep.
6. Movie gets made (2007) After 10 years of sub-par episodes, The Simpsons Movie is finally released, recycling 15-year-old storylines, including Marge questioning Homers ability to be a good husband and the fact that theres nuclear waste in Lake Springfield. (Instead of a three-eyed fish, theres a thousand-eyed squirrel.) Too little, too late.
5. Homer Sings Opera (Homer of Seville, Sept. 30, 2007) What happens when you cant write for a character any more? Change the character! In this recent episode, it was discovered that Homer was a talented opera singer. But havent we heard him sing before, and he was always terrible? Yes, but he can sing really good when hes lying down. That makes it okay.
4. Maude Flanders Dies (Alone Again, Natura-Diddly, Feb. 13, 2000) Hmmhow to make Ned Flanders even less funnyI knowKILL HIS WIFE. Once Maude gets shot, and Flanders is made a widowed father of two, we are no longer allowed to ever laugh at the man ever again. Shooting her with a T-shirt cannon at a NASCAR race doesnt make it okay.
3. Worst Episode Ever (Saddlesore Galactica, Feb. 6, 2000) We would forgive the Simpsons writers for recycling a plot (Lisa got a horse in the third season, while Bart gets one in this episode) if the episode was any good. And when one of your characters (Comic Book Guy) points out that you recycled the plot, and wears a shirt that says Worst Episode Ever, well
2. Phil Hartman Dies (May 28, 1998) He delighted us on Saturday Night Live, but even his purely vocal roles on The Simpsonsinept lawyer Lionel Hutz, B-movie actor Troy McClure and even his single turn as Barts Bigger Brother Tomcaptured our hearts. Disappointing doesnt even come close to how we felt when he was killed by his wife in a murder-suicide.
1. Maggie Shoots Burns (Who Shot Mr. Burns? - Part Two, Sept. 17, 1995) In the previous season finale, Mr. Burns had blocked out the sun over Springfield, only to get shot for being such a miserable bastard. The season premiere took us into the Law & Order stage, narrowing a town full of suspects down to the Simpsons clan, and finally down to...Maggie. Sigh. We were really hoping it was Tito Puente.
20. Homer's Life Dissected (Homer's Enemy, May 4, 1997) While it was entertaining to watch new character Frank "Grimey" Grimes experience a mental meltdown as the high points of Homer's sitcom life (astronaut, country singer manager, etc.) were constantly rubbed in his face, viewers at home were forced to confront the sheer ridiculousness of the show.
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