Where Did THAT Come From – Milo & Coolsville

In our silly lil game, we sometimes see things pop in that we have no clue as to their Origin. They seem familiar, but we just can’t pinpoint from where. So that is why we decided to make a fun lil reminder out of it. To let you know just Where did THAT Come From?

The Simpsons is the longest running sitcom ever and over its storied history, fans have divided over classics versus new episodes versus I like this or that versus rubber versus glue versus insert a reason to be divisive. I am a self-proclaimed uber fan of the show obviously but during the run of said show, I have had moments that brought me joy regardless of the season. Milo is one of those. Originally voiced by the tremendous talent that is Jack Black (Tenacious D y’all!), when Milo appeared, I was all in. Woo hoo! A nemesis for Comic Book Guy! Picture me standing up and vigorously applauding the showrunners of the Best. Show. Ever. I like to think Milo and Coolsville is the sort of thing any fan of The Simpsons worth their salt would know about but alas, we live in a world where everyone can’t be as geeky as me. Sadness aside, that’s where it’s pretty damn cool that I live in a world where I have an outlet to share Simpsons info with other humans connected across a big honking globe spinning out of control in a gigantic old universe. Cosmically speaking, it’s insignificant and overwhelmingly awesome. But I’m digressing… let’s dig into the TV series to find Milo & Coolsville… the latest premium offering for 150 donuts.

“Husbands and Knives” (S19:E7)

Bart is bored at the Android’s Dungeon. “Superman dies. Aquaman dies. Casper dies. Caveman Robin. Black Robin. Born Again Robin.” Everything is lame or he already has it. Bart is excited when he finds a Wolverine comic with pop out claws but opening it causes Milhouse to get scratched, cry on the comic, and be forced to pay CBG 25 bucks aka the money Yaya Sofia gave Milhouse for Orthodox Easter. Bart tells CBG he should be nicer but he’s snarky as usual and points out places they could buy comics at instead like the dry cleaners or the mattress store or Coolsville, the new comics place across the street.

“Philip K. Dick!” Someone built a competive store across the street! All the kids leave after Bart points out that nothing in comics really happened and CBG kicks his customers out.

The kiddos of Springfield promptly meet Milo who is one hip dude. Coolsville has free Japanese hard candy (prawn/miso/dolphin), Korean pop covers of Tom Jones songs, and Milo actually thinks comics should “be read and enjoyed, not hoarded and then sold when you get divorced.” Milo is cool but not mainstream, wears a pork pie hat and actually knows a lot about comics.

More importantly, he actually wants to know what the kids think about important questions like who is stronger, Mulk or Thung?

I think dropkicking a tidal wave wins that debate but maybe that’s just me. Milo even gets alternative comic creators to show up for signings like Alan Moore (Watchmen/V for Vendetta/The Killing Joke), Art Spiegelman (Maus), and Dan Clowes (Ghost World/Eightball). That’d certainly be a signing I’d sell a small child to go to, err, I mean really enjoy visiting. Even Lisa is enticed by the stores offerings.

The fact that all three funny book legends voiced themselves is even better. As if this couldn’t get better, CBG shows up.  Maybe he’s still upset that a Jabba the Hutt standee bears such a striking resemblance to him. CBG is there to declare that Milo is not “one of us” (google goo… one of us… google goo) because he has a girlfriend. Her name’s Strawberry.

CBG tries to entice the children back to the Dungeon with ninja weapons but they are more into Milo’s aesthetic. Plus, selling weapon of the Orient to children is weak. CBG starts wrecking Milo’s shop with a katana. Moore, Spiegelman, and Clowes stand off against CBG as the League of Extraordinary Freelancers to defend Coolsville. God I love writing sentences like that.

Comic Book Guy sells his store to Marge who became unconfident in her figure courtesy of a Wonder Woman standee at Coolsville, had a bad experience at the gym (LA Body Works), and was inspired to open “a gym for regular ladies.” Phew… excitement overload. There’s lots of great geek references in the episode I didn’t point out. It’s all certainly worth a watch.

Weirdly, they set up Milo and Coolsville in this episode but don’t really wrap up that plotline. Well, we do see the Freelancers flying in the sky at the end so I guess that counts.

The Android’s Dungeon is back open in later episodes and Coolsville fades away to obscurity. The assumption is the writers didn’t want to make Milo a permanent character since Jack Black wouldn’t be available. Makes sense since Comic Book Guy isn’t in every episode so his nemesis didn’t need to be a permanent fixture but I wouldn’t have cared if he did. Thankfully, we do see Milo again. In “The Day the Earth Stood Cool” (S24:E7), he is among the trendy hipsters doing some midnight bike riding and also one of the people seen at the Springfield Farmer’s Market.

Seems like stuff he’d be into. Although voiced by Maurice LaMarche in his next appearance, Milo returns with dialogue in “Married to the Blob” (S25:E10). This time he shows up to make fun of Comic Book Guy’s singledom during the release party for the new Radioactive Man #1. I laughed out loud when they indicated where he was originally from in the episode. Milo has been writing Twin Peaks fan fiction, sorting Dr. Who’s by hair puffiness and got married to Strawberry, his “actual, non-imaginary, comic-tolerating girlfriend.”

He also pops up to sing in Comic Book Guy’s song of lament about his loneliness in a spoof of the White Stripes.

This might be funny to only me but I find hilarity in Milo portraying Jack White while being voiced by someone besides Jack Black. Later in the episode, the happy couple is at Bi-Mon-Sci-Fi-Con. He and Strawberry are expecting now. Their baby is so hopster it is cosplaying in the womb lol.

I suppose the enmity between Jeffrey Albertson and Milo can’t be too bad since he was invited to CBG and Kumiko’s wedding.

So for this last appearance, I have to vent that I had to re-watch my least favorite episode. The things I do for the people I like here. Start blogging about TSTO they said. It’ll be fun they said. Seriously though… Milo is in “Every Man’s Dream” (S27:E1) making out with his wife at the hipster bar Candace takes Homer to on their first date… shudder.

If you want to read further ventings about this episode, read the recap (or don’t…I’ll understand). Suffice to say I didn’t dislike this one the entire time but I hate the fake relationship more now than I did then and that’s saying something. Anyhoo… there you go. Milo and Coolsville in The Simpsons and now in TSTO if you pay for it. I’m super stoked for the addition and it took a lot not to shout about it from the attic once I heard rumor he was coming. What do you think of Milo? Did you buy him? Sound off in the comments. I’m inspired to reread Watchmen now. I just wish the Milhouse Alan Moore comic from Milo’s first episode actually existed lol. I guess the darker versions will have to do.

TTFN… Wookiee out!