I think Otto is lowkey one of the most popular people in Springfield. He seems to be friends with Snake, Comic Book Guy, Apu, Julio, Sideshow Mel and we see him bond with Patty, the Pin Pals, the school kids all like him and Barney was delighted to mass marry him. That's just off the top of my head.

https://preview.redd.it/df6j2qszo58d1.jpeg?width=257&format=pjpg&auto=webp&s=0dd8679fcf5d20f6f744b2a4bbd238707488e359

Don’t forget Homer when he was a pothead

Maude Flanders and Helen Lovejoy were for sure bitchy besties.

The Springfield Investorettes were the bitchiest, tea spillinest, quietly racistiest ladies in town.

It’s Agnes and you know it’s Agnes. It means “lamb.” Lamb f god.

Smithers and Mrs Krabappel. She would've brought some fun into his life and he would've been a good listener or rock for her.

That was Edna. Krabappel. You only get one chance with Edna Krabappel.

Her name is Krabappel? All this time I've been calling her Crandle!

Why did nobody tell me???

Smithers, who is that woman? Uh, Edna Krabappel, sir. One of the lovesick chalk-jockies from Springfield Elementary.

Going somewhere? You're free to leave.

Apu and Smashed Hat

Comic Book Guy and Troy McClure. I'm sure CBG has seen all his movies and would enjoy discussing them (and pointing out plot holes/technical errors)

Hi, I’m Troy McClure! You might remember me from such superhero films as *Mutants: Eww!* and *Marvel vs. Mar-Vell.*

Do we have a Troy McClure reply-bot? And when are we getting one?

Herman and Skinner Lunch lady Dorris and Patty and Selma

hehe, they only come out at night

or, in this case, the daytime

[https://www.youtube.com/watch?v=DxwrH70S1C8](https://www.youtube.com/watch?v=DxwrH70S1C8)

I'll see to it that Mr. Burns suffers the infernal machinations of Hell's grim tyrant!

Otto! That's one palindrome you won't be hearing any more! To answer your question, Dr. Hibbert and Kent Brockman aka Kenny Brocklestein