The Simpsons is reaching another unbelievable milestone this Sunday, as the show airs its 500th episode. To mark the occasion, we thought we'd take another look at our favorite peripheral characters from the series.

With hundreds of Simpsons characters now introduced, it can be a bit tricky figuring out which are "peripheral" at this point, especially since 23 seasons of the show means that there's now been enough time for even the more minor characters to appear many times. That being the case, to come up with this list, we eliminated characters that are shown often enough to be considered "regulars", including the likes of Moe, Milhouse, Mr. Burns, and Smithers or some of the most frequently seen recurring characters such as Krusty, Apu and Principal Skinner. After all the bigger characters were removed, we narrowed down our list to the 25 peripheral characters we consider the very best.

#25:+Bumblebee+Man

¡Ay, ay, ay! ¡Es el Hombre Abejorro! ¿Qué más podemos decir?





#24:+Disco+Stu

"Disco Stu likes disco music." That much is for sure. Mentally stuck in the disco era, Disco Stu does his best to keep it cool and remember the good times. Usually found in his leisure suit (with rhinestones) and massive platform shoes, Stu is just trying his best to keep disco alive. Just remember, "Disco Stu doesn't advertise."





#23:+Dr.+Nick+Riveria

Hank Azaria

Whenever someone says, "Hi, everybody!" in a Ricky Ricardo-like accent there can only be one response: "Hi, Dr. Nick!" Everyone's favorite quack doctor arguably has a better bedside manner than Dr. Hibbert (Dr. Nick would never laugh at your condition) but a lot less medical knowledge (some would say Dr. Nick has no medical knowledge whatsoever). But when you're short on cash, as the Simpsons often are, Dr. Nick's pretty much your only choice in town.





#22:+Mr.+Teeny

Dan Castellaneta

The seventh "Mr. Teeny" in a proud line, Louis "Mr. Teeny" Toot faithfully serves Krusty as his driver, butler and eventual organ donor. While we know that much to be true, much of Mr. Teeny's life still remains a mystery – with questions ranging from whether Teeny is a chimpanzee or gorilla to whether he is a he at all! What we do know for sure however, is that even though Krusty finds him to be less than sufficient (preferring Mr. Teeny #3), we find Louis Toot to be one of our favorite citizens of Springfield.





#21:+Duffman

Hank Azaria

Duffman is the mascot and spokesperson for the Duff Beer Company. Showing a resemblance to the Budweiser "Bud Man," Duffman is the perfect corporate mascot. Decked out in blue spandex with a giant Duff logo on his chest, Duffman proudly wears his Duff Beer utility belt (full of beers) and Duff hat… and cape. Referring to himself in the third-person, Duffman may be the coolest character in the Simpsons universe. Really, how can you get any cooler than thrusting your hips in a direction instead of pointing - "Duffman thrusting in the direction of the problem."





#20:+Hans+Moleman

Dan Castellaneta

Although he looks like a decrepit old man, Hans Moleman revealed in the fourth season episode "Selma's Choice" that he's actually only 31 years old -- his old looks stem from his heavy drinking. Hans has been in some classic scenes and had some memorable lines over the years, such as the time cult deprogrammers accidentally captured Hans instead of Bart and returned him in full Bart garb ("Mom, Dad, I missed you. Cowabunga, dudes!") or when he was in the stands screaming for blood during Bart and Lisa's hockey match.





#19:+Snake

Hank Azaria

Snake is a Simpsons character who can make almost any line funny, thanks to his voice alone. It's hard to explain the odd mixture of thuggishness and pseudo-suaveness Snake has in his voice, but it certainly is amusing, especially the way he stresses the last word in most sentences, whether it be his own name or, "Alright, I'm taking this thing to Mexico!" Often arrested, Snake seems to snake his way out of jail pretty easily, always around to break some laws in Springfield for our comic enjoyment.





#18:+<a+class='autolink'+href='https://stars.ign.com/objects/922/922629.html'>Fat+Tony</a>

Marion Anthony "Fat Tony" D'Amico is the boss of the Springfield Mafia, er, waste management business. As parodies of all the major mafia characters in pop culture, Fat Tony's crew engages in such friendly activity as shaking down pretzel businesses, hosting illegal poker games, and supplying the school cafeteria with milk from rats. One of Fat Tony's most memorable lines was in the eighth season episode "The Twisted World of Marge Simpson": "You see, my wife, she has been most vocal on the subject of the pretzel monies. 'Where's the money?' 'When are you going to get the money?' 'Why aren't you getting the money now?' And so on."





Lionel Hutz, Mayor Quimby, Grimey and more on page 2…