50 Haikus based on 50 characters:

In order of my appreciation for the characters. If one of your favorite characters isn't on this list, feel free to write a haiku about them in your spare time.

(Smithers)

Nerdy assistant

Working hard and secretly

Loving his old boss

(Moe)

Sadness comes quickly

To the tavern owner's eyes

Spiting his plain face

(Mr. Burns)

Money and power

Cause the decrepit man joy

In his busy plant

(Chief Wiggum)

Police officer

Keeping evidence off-guard

Never very smart

(Ned Flanders)

Religious young man

Training his kids to be good

Neighbor envy, much?

(Ralph)

Deep inside his brain

There is much we cannot see

Ralph's a special kid

(Sideshow Bob)

Constantly abused,

Psychological insane

Thoughts keep him locked up

(Milhouse)

Butt of all the jokes

Kid with glasses pushed around

Loves his friend's sister

(Kirk van Houten)

Dweeb to the extreme

His wife left him unfulfilled

Son is all he has

(Sideshow Mel)

An apt replacement

Causes drifting between Bob

And Krusty the Clown

(Comic Book Guy)

Overweight, geeky,

Standing at the counter of

The town's comic store

(Maggie)

Little smart baby

Understands and responds well

Cannot speak out loud

(Dr. Nick)

The town's super quack

Calling out in infamy,

Bargain advantage

(Principal Skinner)

Little mama's boy

Stricter than the teachers are

Adores Edna K

(Apu)

Convenience store clerk

Hailing in from India

He has spawned eight kids

(Prof. Frink)

Celibate as Moe

With a brain to calibrate

Way challenging math

(Mrs. Krabappel)

Sassy school teacher

Likes to tease the principal

Doesn't mind students

(Willie)

Crazy ranting Scot

Always cleaning never seen

As a gentleman

(Nelson)

Always teasing Bart

Never will he admit to

Insecurities

(Rod Flanders)

Followed example

Set by his devout father,

He's his pride and joy

(Lou)

Second in command

Though he's smarter than the chief

Seeing things he won't

(Otto)

Tripping bus driver

No one's such a music fan

As this junkie dude

(Krusty)

This sadistic clown

Causes pain and misery

For all his sideshows

(Bart)

Bratty ten-year-old

Never taught to behave right

His daddy chokes him

(Luann van Houten)

Left her husband fast

Took a ride with other men

Never resettled

(Todd Flanders)

Cute and innocent

A little cherub gently

Grins at his good faith

(Dr. Hibbert)

Joking doctor takes

His job quite seriously

Compared to the quack

(Carl)

Sits at the barstool

Giving meaning to Lenny

Without him, nothing

(Lenny)

Always seen with him

Carl likes to drink beer with Len

The man he completes

(Lisa)

Cheesy democrat,

Props for having high IQ

Of the Buddhist faith

(Marge)

Loving caring mom

Three kids really wear you down

Homemaker's her job

(Kent Brockman)

Stupid anchorman

Always irrelevancies

Show up in the news

(Rev. Lovejoy)

Conservative priest,

Helping all who listen with

Leaving those who don't

(Cletus)

Silly hillbilly

Put in incest many times

IQ worse than Ralph

(Hans Moleman)

Strange elderly man

But as luck just must turn out

He's but thirty-one

(Homer)

Lazy stupid man

Overeats and binges beer

Why does Marge love him?

(Agnes Skinner)

Nagging old mother

To her middle-aged baby

Seymour needs some love

(Barney)

Big fat drunken guy

Always drinks beer and is soon

Intoxicated

(Snake)

Multiple-offense

Felon makes his getaway

Too proud to return

(Patty)

Tolerable twin

The one who doesn't leer at guys

Because she likes girls

(Eddie)

Third and seldom speaks

Behind the mask of Lou he seems

Just superfluous

(Bumblebee Man)

Mexican insect

Or just a man in a suit

Facing deep anguish

(Abe)

Crazy old grandpa

Father of the lazy one

Memories now lapse.

(Martin Prince)

Goody-two-shoes kid

Classmate with the hell raiser

How does he manage?

(Selma)

Twin with lots of lust

Makes Luann look settled in

Never stops the fun

(A three-part haiku for Jimbo, Dolph, and Kearney)

Three distinct bullies

All band together to cause

Mischief in the halls

One is short and bald

Another one is tall and has

A knit cap on his head

The last one sporting

A tuft of short, straight brown hair

All are merciless

(Cookie Kwan)

Asian realtor

"So good you'll believe it's new

But it's just valued"

(Brandine)

Fertile country lass

Spawns more kids than Apu has

And not luck of the draw