Jake
When you think of Springfield, it’s a vast and populated place. It’s like a little universe full of funny and interesting characters, which stretch beyond the main family.
This gets me thinking of how amazing it would be if they would consider spin-off shows with some of their well-known or not so well-known characters. They did it once with the season 8 episode “The Simpsons Spin-Off Showcase”.
This has been the hardest list to compile since our Top 25 Simpsons Episodes post a while back. This list was originally going to be the Top 10 Simpsons Characters of all Time, but then more and more characters kept springing to mind. Then it went up to 50 and then 100 at one point, but after many hours of debate, protests and fighting in the office, we managed to negotiate and whittle it down to a selection of our fave 25 characters, although some of us still debate them.
Personally, I could easily just do a list of all the characters that Albert Brooks and the late Phil Hartman provided their voices for, because they are all standout characters. Think Hank Scorpio, Troy McClure, Brad Goodman and Lionel Hutz!
Another thing we have to mention is that only one member of the Simpsons family appear in our list. I bet you can probably guess who it may be!
These are our choices for the 25 best characters to ever appear on the Simpsons.
25. Lindsey Naegle
Lindsey Naegle is a resident of Springfield and is often known as Springfield’s residential business link. Over the years Lindsey has popped up in several capacities, seemingly working at a different job every time she appears in an episode. Her job titles have included network executive, marketing researcher, financial planner, public relations consultant, venture capitalist, advertising executive, phone company executive, insurance salesperson, and executive with the Child Development Group. She also formed an anti-youth group, SSCCATAGAPP (Singles, Seniors, Childless Couples and Teens and Gays against Parasitic Parents),
Voice – Tress McNeille
First Appearance – “The Itchy & Scratchy & Poochie Show”
Best Episode – “Marge vs. Singles, Seniors, Childless Couples and Teens and Gays”
24. Lyle Lanley
Voiced by the legend of Phil Hartman, Lyle Lanley is a con artist and shyster who sells faulty monorails to several towns, including our beloved Springfield. Lyle Lanley manages to convince the town meeting on deciding how to spend three million dollars. The town had managed to collect this money in fines from Mr. Burns dumping toxic waste. The town was on the verge of voting to use the money to repair Main Street when Lanley successfully made his musical sales pitch for the monorail. He then chose Homer to be the conductor, seemingly at random as he makes his escape to Tahiti on the last day of class.
Voice – Phil Hartman
First Appearance – “Marge vs the Monorail”
Best Episode – “Marge vs the Monorail”
23. Tab Spangler
Tab Spangler is the counselor of the fat camp, Serenity Ranch, Bart is ento to after he gets fat from Scammer and Z-Dog snacks from the new school vending machines. A great funny character by Albert Brooks. In fact all the many characters that Brook has voiced for the Simpsons over the decades have been some of the most memorable.
Voice – Albert Brooks
First (and only) Appearance -“The Heartbreak Kid”
Best Episode – “The Heartbreak Kid”
22. Colonel Leslie “Hap” Hapablap
There is only one guy you want to provide the voice of an Air Force Colonel and that would be ex- drill sargent R. Lee Ermey after his standout performance in the motion picture Full Metal Jacket. Hapablap apparently also has a penchant for using bad language and cussing out his fellow soldiers whenever he doesn’t get his way. “Sweet Enola Gay, son! I’m going to come in there and corpse you up—corpse you up and mail you to mama!”
Hapablap actually references Full Metal Jacket, with a quote from the film: “What is your major malfunction?!”
Voice – R. Lee Ermey
Best Episode – “Sideshow Bob’s Last Gleaming”
Best Quote – “Sideshow Bob’s Last Gleaming”
21. Frank Grimes
Franklin A. Grimes, Sr., or “Grimey” as he liked to be known, was an employee of the Springfield Nuclear Power Plant and the self-declared enemy of Homer Simpson. Frank Grimes was a hard worker, who had to earn everything the hard way, which probably is why he is irritable, grumpy, and so easily annoyed. Sadly, was killed trying to show everybody how incompetent Homer is.
Voice – Hank Azaria
First (and only) Appearance – “Homer’s Enemy”
Best Episode – “Homer’s Enemy”
20. Mindy Simmons
She’s the female equivalent to Homer, she is also pretty sexy too! Mindy Simmons was an employee of the Springfield Nuclear Power Plant and when Homer first meets her finds himself extremely attracted to. She likes the same things as Homer, like donuts, chicken drumsticks and beer.
Voice – Michelle Pfieffer
First Appearance – “The Last Temptation of Homer”
Best Episode – “The Last Temptation of Homer”
19. Drederick Tatum
Based on Mike Tyson Drederick Tatum is a former boxer who resides in Springfield. Tatum is known for his extremely large size, his success at boxing (former Olympian and World Heavyweight Champion) and his history of violent outbursts. He seems to have quit boxing though in recent years.
Voice – Hank Azaria
First Appearance – “Homer vs Lisa and the 8th Commandment”
Best Episode – “Homer vs Lisa and the 8th Commandment”
18. Otto Mann
Otto Mann, who was originally known as Otto the School Bus Driver prior to Season 8, is a former stoner and school underachiever who now works as the bus driver for Springfield Elementary. Well known for his party tendencies and using slang talk like “dude” and “man”, a lot. Despite their age differenceshe is friends with Bart on some occasions, and dreams of starting his own rock band to become a celebrity, all while getting the school bus into trouble one time after another.
Voice – Harry Shearer
First Appearance – “Homer’s Odyssey”
Best Episode – “The Otto Show”
17. Kent Brockman
Kent Brockman (Kenny Brockelstein) is a local TV news ‘personality’ for Channel 6. He hosts the Channel 6 weekday news as well as Smartline, a local current affairs show, and also Eye on Springfield, which focuses mostly on Springfield’s entertainment news.
Voice – Harry Shearer
First Appearance– “Krusty Gets Busted”
Best Episode – “Homer Badman”
16. Dr. Julius Hibbert
Dr. Julius Murphy Hibbert II, M.D., or simply just better known as Dr. Hibbert, is Springfield’s most prominent and competent doctor, though he sometimes makes no effort to hide or make light of his high prices. Hibbert is very good-natured, and is known for finding a reason to laugh at nearly every situation. He is often assisted by Dr. Nick Riviera who is up next by the way!
Voice – Harry Shearer
First Appearance– “Bart the Daredevil”
Best Episode – “The Way We Was”
15. Dr. Nick Riviera
“Hi Everybody!” Dr. Nicholas Riviera M.D. is a quack physician who studied at dubious medical schools, although he claims to be “just as good as Dr. Hibbert M.D.”. He also inventor of the ‘Juice Loosener’ and ‘Sun & Run.’
Voice – Hank Azaria
First Appearance – “Bart Gets Hit by a Car”
Best Episode – “Homer’s Triple Bypass
14. Snake Jailbird
Chester “Snake” Turley, or Snake Jailbird, Albert Knickerbocker Aloysius Snake, also known as Professor Jailbird and Detention Bird, is a recidivist criminal, always getting arrested, but rarely appearing to stay in prison. He speaks with a “Valley Boy” accent and has a tattoo of a snake on his arm, which is presumably the source of his nickname. He is partial to fast cars and fast women, and has a knack for reckless abandon.
Voice – Hank Azaria
First Appearance – “The War of the Simpsons”
Best Episode – “Reality Bites”
13. Duffman
Barry Huffman, known mostly by his working name Duffman, is the mascot and spokesman for the Duff Beer company. There are actually multiple people who play Duffman.
Voice – Hank Azaria
First Appearance – “The City of New York vs. Homer Simpson“.
Best Episode – “Eternal Moonshine of the Simpson Mind”
12. Rainier Wolfcastle
Rainier Luftwaffe Wolfcastle is an Austrian, musclebound action movie star and a parody of Arnold Schwarzenegger. Wolfcastle is a veteran of many action movies, most notably the McBain series. Wolfcastle began his acting career as early as childhood in Austria, appearing on long TV commercials advertising bratwurst.
Voice – Harry Shearer
First Appearance – “The Way We Was”
Best Episode – “Radioactive Man”
11. Superintendent Gary Chalmers
Gary Chalmers is the superintendent of Springfield’s school district. Chalmers is a temperamental and whimsical man unfortunately vested with authority. Chalmers is known for throwing open the doors to the room and bellowing “SKINNERRRRR!!!” or “SEYMOUR!!!”, to which Seymour stammers, “S-Superintendent Chalmers!”
Voice – Hank Azaria
First Appearance – “Whacking Day”
Best Episode – “Sweet Seymour Skinner’s Baadasssss Song”
10. Hank Scorpio
My favourite Albert Brooks character, Hank Scorpio is an evil genius and owner of Globex Corporation. Scorpio, despite being an evil genius, proved to be an ideal boss, welcoming the Simpson family with a beautiful home and a friendly, relaxed, non-authoritative employer attitude
Voice -Albert Brooks
First Appearance – “You Only Move Twice”
Best Episode – “You Only Move Twice”
9. Lionel Hutz
Lionel Hutz, aka Miguel Sanchez, aka Dr. Nguyen Van Phuoc, is a lawyer in Springfield, albeit an incompetent one. He was always desperate for cases, few of which he actually won. Hutz was financially insolvent, extremely poor and willing to do nearly anything for money. In his final appearance he was running Red Blazer Realty. The character of Lionel Hutz, along with other Phil Hartman characters, was retired after the actor’s death.
Voice – Phil Hartman
First Appearance – “Bart Gets Hit by a Car”
Best Episode – “Marge in Chains”
8. Troy McClure
My favourite Phil Hartman character, Troy McClure is a cheesy B-movie actor who had fallen on hard times. He was often seen shilling for shoddy products or hosting questionable shows. He appeared from Season 2 until Season 10. Since then, Troy, along with 2 other Phil Hartman characters were retired in his honour.
Voice – Phil Hartman
First Appearance – “Homer vs. Lisa and the 8th Commandment”
Best Episode – “A Fish Called Selma”
7. Apu Nahasapeemapetilon
Apu is the Indian immigrant proprietor of the Kwik-E-Mart, a popular convenience store in Springfield, and well known for his accent and catchphrase, “Thank you, come again.” Apu has had a lot of storylines in the Simpons over the seasons and we’ve seen him meet, and marry Manjula and have eight children over the years although they are octuplets!
Voice – Hank Azaria
First Appearance – “The Telltale Head”
Best Episode – “Homer and Apu”
6. Principal Seymour Skinner
Walter Seymour Skinner, formerly known as Armin Tamzarian (let’s not talk about that!), is the principal of Springfield Elementary School, and a stereotypical educational bureaucrat. He struggles to control the crumbling school and is constantly engaged in a battle against its inadequate resources, apathetic and bitter teachers, and often rowdy and unenthusiastic students, Bart Simpson being a standout example. A strict disciplinarian, Skinner has an uptight, militaristic attitude that stems from his years in the United States Army as a Green Beret, which included service in the Vietnam War, where he achieved the rank of a sergeant, according to his rank insignia. As a result of his service in the Vietnam War, he is often plagued by horrible memories of his involvement via post traumatic stress disorder, sometimes even happening at the most inopportune of times.
Voice – Harry Shearer
First Appearance – “Simpsons Roasting on an Open Fire”
Best Episode – “Sweet Seymour Skinner’s Baadasssss Song”
5. Moe Szyzlak
Morris “Moe” Szyslak is the bartender of “Moe’s Tavern”, a Springfield bar frequented by Homer and his friends.
Moe is portrayed as often irritable and rude to all except his bar friends Homer, Lenny, and Carl, whom he sometimes treats as respected customers as opposed to his everyday drunks like Barney. His easy-to-lose harsh temper usually turns down women and finding a girlfriend for Moe has therefore been a running joke, from indulged sexual abstinence to unsuccessful suicide attempts to dating generally rejected women. However, contrary to his personality, Moe has been seen helping others in need. These include saving marooned school children, giving food to a famished village, and saving people from a rampaging flood.
Voice – Hank Azaria
First Appearance – “Simpsons Roasting on an Open Fire”
Best Episode – “Flamin’ Moes”
4. C. Montgomery Burns
Charles Montgomery Plantagenet Schicklgruber Burns, also known as Monty Burns, Montgomery Burns, C.M. Burns and Mr. Burns is a rich, influential citizen of Springfield and the main antagonist of The Simpsons. He is the owner and manager of the Springfield Nuclear Power Plant. Burns is Springfield’s richest and most powerful citizen. His net worth has been stated to be in the billions and in one instance was pegged at exactly $1,800,037,022
Voice – Harry Shearer
First Appearance – “Simpsons Roasting on an Open Fire”
Best Episode – “Rosebud”
3. Sideshow Bob
Dr. Robert “Bob” Underdunk Terwilliger, Jr., better known by his stage name, Sideshow Bob, which he got when he was Krusty the Clown’s sidekick. Bob is a self-proclaimed genius, member of the Republican Party, champion of high culture, former children’s entertainer-turned-criminal mastermind and Bart Simpson’s nemesis. He loves Gilbert and Sullivan operettas and is known for his huge feet, which have gotten him into trouble on more than one occasion. Watch out for those rakes!
Voice – Kelsey Grammer
First Appearance -“The Telltale Head”
Best Episode -“Cape Feare”
2. Krusty the Klown
Herschel Shmoikel Pinchas Yerucham Krustofsky, also formerly known as Rory B. Bellows, better known by his stage name Krusty the Clown or just Krusty, is the cynical, burnt-out, addiction-riddled smoking clown host of Bart and Lisa’s favourite TV show The Krusty the Clown Show.
Krusty the Clown was originally intended to be Homer Simpson’s secret identity to create a problem between Bart’s love for Krusty, and his dad. This was later scrapped to keep Krusty as a frequent character in the series instead.
Voice – Dan Castellaneta
First Appearance – “The Krusty the Clown Show” (The Simpsons shorts)
Best Episode – “Krusty Gets Kancelled”
1. Homer Simpson
You knew it was going this way didn’t you?
Homer Jay Simpson, Sr., also known as Homer Samson, Homie, Colonel Homer, Dancin’ Homer, Mr. Plow, Captain Wacky, Homer Thompson, Max Power, Cornelius Talmadge, El Homo, The Brick Hithouse, Angry Dad, Rock Strongo, Lance Uppercut, The Pie Man and many more, is one of the major characters of the show and the spouse of Marge Simpson and the father of Bart Simpson, Lisa Simpson, and Maggie Simpson. Homer is overweight, lazy, and often ignorant to the world around him. Though Homer has many flaws he has shown great caring, love, and even bravery to those he cares about. We love you Homer!
Voice – Dan Castellaneta
First Appearance – “Good Night” (The Simpsons shorts)
Best Episode – “Homer Badman”
Sources for this article include…
The Simpsons World – The Ultimate Episode Guide. Well worth a read if you love the show!
This article uses material from The Simpsons wiki at Wikia and is licensed under the Creative Commons Attribution-Share Alike License.
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