This was a really hard article to create. I love so many of the side characters that Matt Groening and his team have created, but alas, this is but one article and not a twelve book series. I decided to stick with the number eight since most of the Simpsons should live in a base eight world, even though they don't. Let's do this.
1. Groundskeeper Willie
Groundskeeper Willie first appeared in episode 27 in the "Principal Charming" episode. Since then, Willie has ripped his shirt off and/or yelled in his Scottish accent more times than I have ever been able to successfully rip my shirt off (that number would be set in a world of base 0).
2. Ole Gil
Poor, poor Gil. He just wants a piece of that American dream. Gil has been a favorite of mine since the Cookie from the West side scene. I think we can all relate to Gil and him feeling like he's stuck in life, though the difference is he actually stays stuck.
I honestly wish they would have made an entire episode based on a McBain movie, (unless that happened in one of the newer seasons and I just haven't seen it?) Luckily, someone kind of did it for us. McBAINNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN!
4. Comic Book Guy (Stan Lee Too?)
Comic Book Guy's sarcasm melts my heart with joy and complete hatred. He is the epitome of every comic book shop owner I've met and hated (though I've also liked plenty of owners as well, like the owner of this place.) One of my favorite episodes is when Stan Lee shows up to the shop and refuses to leave. The ole' hero-to-annoyance gag. "THE THING WILL FIT IN YOUR BATMOBILE!"
5. Principal Skinner/Superintendent Chalmers
I know this is two different characters, but it's their dynamic that I like more than either one of them alone. One of the scenes I like to quote the most is when the superintendent comes over to Skinner's to eat and he's trying to hide the fact that he burnt the food. "Aurora Borealis!?"
6. The Canyanero
To me, the Canyonero is a character in itself. I think I may like it more than Maude (good riddance.) Remember, the answer is always... CANYONEROOOOOOOOOOOOOOOOOOOOO.
Cletus is a representation of about a quarter of the people I saw growing up in Garland, Texas. Hell, I was probably a little Cletus-like from time to time. Extra shout out to Tiffany, Heather, Cody, Dylan, Dermott, Jordan, Taylor, Britney, Wesley, Rumer, Scout, Cassidy, Zoe, Chloe, Max, Hunter, Kendall, Caitlin, Noah, Sash, Morgan, Kira, Ian, Lauren, Cubert, Phil.
Milhouse and I share a bond; we were basically the same person when I was a kid. I'm not sure who my Lisa was when I was younger, but I'm sure I had a million like her reject me. I even made him the strongest character in a card game I created. (I gotcho back, Mil.) As an adult however, I find myself often thinking like Milhouse in this scene: