Few shows can top the number of characters The Simpsons has. While the show’s titular family is obviously front and center, the town of Springfield is filled with memorable and unusual characters who help fill out this hilarious world – some of which have been around since the very beginning.
Now in its 30th season, plenty of those wonderful side characters have been given the chance to come into the spotlight a lot more. We often see episodes that revolve around some of the more interesting characters the Simpsons know. Looking back over the years, here are the side characters from the show who have had the most appearances.
Apu Nahasapeemapetilon is the hardworking and friendly owner of Springfield’s favorite convenience store, the Kwik-E-Mart. He made his first appearance in the first episode of season one, "The Telltale Head." Apu appears frequently on the show from his place behind the counter of the Kwik-E-Mart, but has also become involved in some of the Simpsons biggest adventures.
Some notable appearances from Apuincludese when he sought his United States citizenship, his arranged marriage to Manjula, and his fathering of nine babies. The character has recently been the subject of controversy but it’s likely he’ll be around for years to come.
Milhouse Mussolini Van Houten is Bart Simpson's awkward, timid best friend. Whether welcome or not, Milhouse is often inserting himself into the Simpsons life, usually unwelcome. He tags along on many of Bart’s adventures which usually end poorly for him, and also harbors romantic feelings for Lisa.
Milhouse actually made his first appearance in the world of The Simpsons in a Butterfinger commercial. Some of his most notable appearances include falling in love with a new girl at school, being cast as Fallout Boy in the Radioactive Man movie, and finding a kindred spirit while trying to rescue the lemon tree from Shelbyville.
8 Kent Brockman
Kent Brockman is the lead anchor of the Channel 6 news. He’s often seen as a vain and fairly unprofessional newscaster, and while he doesn’t appear much off the television screen, he is a regular presence on the show, offering the latest news in Springfield.
Brockman’s first appearance came in season one's episode "Krusty Gets Busted." Since then he has made larger appearances his fear-inducing reporting during a string of burglaries, struggles to keep up with a changing media world, and when he was fired for swearing on live television.
7 Chief Wiggum
Chief Clancy Wiggum is the portly and incompetent police chief in Springfield. He is lazy when it comes to his work but often tags along on some of the wilder adventures on the show. He is the father of Ralph Wiggum and usually seen with his fellow officers Lou and Eddie.
Wiggum’s first appearance was in "Homer's Odyssey" in season one. Since then he has been a large part in the show with his investigation into the shooting of Mr. Burns, being replaced by Rex Banner and his brief spin-off, "Chief Wiggum, P.I."
6 Abe Simpson
Abe Simpsons is the patriarch of the Simpson family, yet he receives none of the respect that position suggests. He is a regular member of the family adventures unless the family just feels like leaving him in the nursing home.
Abe goes all the way back to the very first episode of the show that was aired, “Simpsons Roasting on an Open Fire.” Some of his most notable appearances include falling in love with Marge’s mother, battling with Mr. Burns over priceless paintings, and trying to recapture his youth by working at a fast food restaurant.
5 Krusty The Clown
Krusty the Clown is the most popular children’s entertainer in Springfield. He hosts a kids’ show that features he, Sideshow Mel, and cartoons of Itchy and Scratchy. Bart, being Krusty’s biggest fan, often gets caught up in the funny man’s depressing real life.
Krusty first appeared in a small sketch on The Tracey Ullman Show before The Simpsons even hit the air. Some of the episodes he was prominently featured in include the horrific Kamp Krusty, his troubles with the IRS, and his show’s cancellation and triumphant return.
4 Ned Flanders
Ned Flanders is the friendly but religiously uptight neighbor of the Simpsons with a particularly annoying way of speaking. His friendly nature means he’s often poking his head into the Simpsons life, oblivious to the fact that Homer despises him.
Ned also made his first appearance alongside his sons, Rod and Todd, in “Simpsons Roasting on an Open Fire.” His most notable appearance includes losing his home in a hurricane, the death of his wife Maude, and his ironic appearance as the devil in a Halloween episode.
3 Principal Skinner
Principal Seymour Skinner is the rigid Vietnam veteran who is in charge of Springfield Elementary. Despite his hard-nosed ways, Skinner gets no respect from the children and is constantly pushed around by his overbearing mother and superintendent Chalmers.
Skinner’s first appearance was also in “Simpsons Roasting on an Open Fire.” He has been in a big part of some classic Simpsons episodes. Some of those appearances include his affair with Edna Krabappel, his misadventure with “steamed hams,” and the discovery that he is not actually the real Seymour Skinner (although we try to just forget that one).
2 Moe Szyslak
Moe is the short-tempered and lonely bartender of Moe’s Tavern. Given how much time Homer spends at that bar, it’s no wonder Moe is such a frequent character on the show. Despite his gruff appearance and attitude, he has been a good friend to the family for years.
Like so man others, “Simpsons Roasting on an Open Fire” is Moe’s first appearance on the show, too. Moe has had such memorable adventures over the years, like taking credit for Homer’s signature cocktail, his attempt at opening a trendy nightclub and, of course, falling for Bart’s many prank phone calls.
1 Mr. Burns
Montgomery Burns is the obscenely rich and incredibly old owner of the Springfield Power Plant. He is one of the eviller characters on the show, though he occasionally shows sign of humanity. As Homer’s boss, he is cruel and punishing, even if he can never remember Homer’s name.
He too made his first appearance in that classic Christmas episode that started it all, “Simpsons Roasting on an Open Fire.” Some of his most memorable and hilarious appearances include shamelessly attempting to win the Springfield film festival, successfully clocking out the sun, and searching for his long-lost teddy bear.