For over three decades, Marge, Homer, Bart, Lisa, Maggie, and the rest of Springfield have showcased simple and satirical life on the fox network. While it can be argued that the quality of the show isn’t what it used to be when it arrived in 1989, there’s no denying that The Simpsons has crafted an important legacy within the landscape of television and pop culture. The Simpsons have over 600 episodes and the show doesn’t seem to be slowing down anytime soon. With a plethora of unique characters throughout its television span, this list will highlight the five best in the show’s history. The new characters in the 2007 feature-length movie will also be considered; however, Marge, Homer, Bart, Lisa, and Maggie will be exempt from the list to give more of the other characters the spotlight. Let’s quickly get started.
Edna Krabappel
First making her appearance in Bart the Genuis, this sassy, grumpy, and somewhat horny caricature of what an American public-school teacher is made a strong impact on arrival, being a fun counterfoil to Bart and the entire community in general. The Simpsons showcase a jaded view of what the public system is, but despite that, the show has gone out its way to highlight that Ms. Krabappel is more than a promiscuous woman who could care less about the kids’ education as The Seemingly Never-Ending Story revealed that she was an opportunistic woman who really did want to help people in need. This helped flesh out the Krabbappel character and made her more grounded and real than some of the other Simpsons regulars. Mrs. Krabbappel is definitely missed within the series, but it’s understandable the show creators retired the teacher out of respect for Marcia Wallace, who sadly passed away on October 25, 2013.
Sideshow Bob
Bart has a slew of enemies in the Simpsons but easily the funniest is Sideshow Bob and his numerous attempts at trying to kill the 10-year-old boy. Real name Robert Underdunk Terwilliger Jr. (try saying that five times fast), he’s the former television personality of Krusty the Clown Show turned wannabe criminal mastermind. Sideshow Bob’s reasoning for wanting to murder Krusty the Clown is sound as the villain was consistently abused by the performer for years. One of the great things about television is that it allows for shows to slow down and explore characters that wouldn’t normally get much time in a feature film. Though tragic, Sideshow Bob’s antics are devilishly fun and somewhat reminiscent of a Tom and Jerry cartoon (or Itchy and Scratchy). Of course, it helps that the voice behind the legendary guest character is Kelsey Grammer, who perfectly voices the exuberant and murderous gleeful star. It’s a shame that we don’t get much of Sideshow Bob these days, but that just makes his appearances in The Simpsons that much sweeter.
Charles Montgomery Burns
Charles Montgomery Plantagenet Schicklgruber Burns, better known as Mr. Burns, is the boss you’ll always hate, but love to watch regardless. From his evil cackle to his devilish demeanor, this devious and greedy owner of the Springfield Nuclear Power Plant is a jaded representation of corporate America and their thirst for power and wealth. In the early stages, Mr. Burns was supposed to be a one-dimensional villain who popped up every now and then; however, the popularity of the character helped the corporate boss become a regular mainstay in the series. Doing that allowed the show to explain who the feeble old man was and how he got into such a powerful position. The circumstances surrounding his rise in power was hilarious, as is the jokes regarding his age, appearance, and lack of strength that barely rivals a baby. However, it’s his assistant Smithers that keeps Burns humanized. Burns may be the embodiment of Ebenezer Scoorge, but even he has a heart of gold every now and then.
Principal Walter Seymour Skinner
At one point in our lives, most of us have had a Principal Skinner around school. His genuine concern for quality education makes him a stiff and hardass on the students; however, the pranks that Bart Simpson pull on the poor man are some of the show’s best moments. It’s not just the pranks that Bart pulls on Skinner that makes him great, it’s everything regarding his outside life. For a man who’s very strict and disciplined, the juxtaposition on him lacking in true confidence or much control in everything around him makes for some hilarious gags throughout Skinner’s time on the Simpsons. However, it’s his intimate relationship with his mother that arguably draws the shows best moments and despite his army background, the fact that he appears incompetent and weak on so many occasions are one of the shows best running gags.
Krusty the Clown
Everyone loves a drunk and unfunny clown, right? One of the interesting facts about the reoccurring character is that Homer was actually intended to be revealed as Krusty the Clown, which is why Herschel Shmoikel Pinchas Yerucham Krustofsky looks like Homer’s long-lost brother. Krusty does represent a sad part of the cynical part of fame, though that’s pretty much the joke of his character. He’s pretty much living the American dream of being an often lazy, irresponsible, coke addicted fiend who gets paid a high amount of money. Krusty’s life may be one of the sadder characters on the show, but the clown has provided plenty of hilarious moments, especially when Sideshow Bob is present.The Simpsons
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