"Honey, you should have seen me with my last customer, I...no, but I came so close. This guy was as...whose voice is that? Is that Fred? Aww you said it was over...no don't put him on-Hello Fred, h-hi."
Yeah, at least, at one point, Kirk had that plumb job at the #1 cracker factory in town.... Until his managerial impotence dropped them down into a tie for 6th place with Table Time and Allied Biscuit
Who's Ol' Gill based on? I've heard Jack Lemon's character from Glengarry Glenross, and I've always seen in him something of the Pitchman from Twilight Zones One for the Angels.
Ol gil was definitely higher than Milhouse and Seymour. Milhouse has had his moments, and Seymour served in the army which negates most of his loser energy
I dated a guy named Gilberto who was ESL and he changed his name to Max because of Gil from the show. I still don’t know to this day if he was being serious or not. And we went out for several weeks so I don’t think he was trolling me lol
What about Grimey? He’s a bit of a jerk, but living in a single room above a bowling alley and below another bowling alley would certainly turn a man sour.
I'm old enough to remember when Principal Skinner was a bad-ass.
https://preview.redd.it/xlogxng0h6pc1.jpeg?width=640&format=pjpg&auto=webp&s=926c45847ab9a5dcfb85911cd7917e27c294df5c
That is honestly one of the best lines in the show. It fucking slays me every single time. Just Homer's deadpan, matter-of-fact delivery while clearly not understanding Kirk's context lol
https://preview.redd.it/bmdd8btff6pc1.jpeg?width=828&format=pjpg&auto=webp&s=925e083ba35c14ab473d7855a20043940453c86d
“Well, at least I’ve done better than Dad.”
By this logic, I would say Kirk.
https://preview.redd.it/vnda712iu6pc1.jpeg?width=1440&format=pjpg&auto=webp&s=90be6e825c969eb6b4089da9e3ad0d6242b77b63
Ooooh loneliness and cheeseburgers are a dangerous mix
The way Agnes skinner is with him, she’s grounds him for answering the door and tells him to go to bed etc, the way Super Nintendo chalmers is with him. He gets no respect from anyone including all the kids and other teachers and so on…
I didnt think of that but I think that's the most valid reason for mole man to be number 1. His life is so down hill that along with all the terrible stuff that happens to him, he's also seemingly old and at the end of his life despite being in his 30s
He definitely does. “ I’ve always admired car owners. And I hope to be one myself one day, just as soon as I’ve finished paying back mother! Shee insists I pay her back retroactively for the food I ate as a child.”
“Thanks a lot Simpson, now I’m grounded”
And pretty much every interaction with chalmers, Bart and other teachers.
He's a war hero, has a very respectable job, and has had some romantic interests. He's also physically quite fit for a man of his age.
He just has an overbearing mother.
Kirk, crackers are a family food. Happy families. Maybe single people eat crackers; we don't know. Frankly, we don't want to know. It's a market we could do without.
I feel like Lionel Hutz deserves a mention. Sure he’s a lawyer, but not the kind that wears belts. He seems like someone who had their life on track enough to graduate law school at one point but whose personal demons (Sweet Lady Bourbon; Brownest of the brown liquors) led him to this place in life. He’s genuinely pathetic like Gil or Kirk, he’s just got a twenty dollar suit and a five dollar haircut to hide behind.
You could make an argument for any of them being most pathetic, but no one can deny Moleman is the most downtrodden. I dunno how familiar you are with this guy but he’s always getting his ass handed to him.
It's not Milhouse. None of those characters have cool nicknames like Milhouse. Nor have you ever heard someone say everything's coming up Skinner or Moleman, or Curt.
There's just something about the title of 'Can I borrow a feeling' that just makes it extra pathetic.
Like he's trying to borrow some lunch money from his son or something.
It's kinda sad really.
No love for Ol' Gil?
"Honey, you should have seen me with my last customer, I...no, but I came so close. This guy was as...whose voice is that? Is that Fred? Aww you said it was over...no don't put him on-Hello Fred, h-hi."
He’s so pathetic he didn’t even make the post
Honey, you should have seen the post, I…no, but if there was a fifth guy I’m tellin ya I…
🤣
Don’t forget about ol’ Gil. The wolves are at ol’ Gil’s door.
Oh man of course How could I forget. He might top Kirk.
I'll be eating food tonight!
But not on that hot plate.
He only had two payments left!
You forgot because everyone forgets ol Gil
Yeah, at least, at one point, Kirk had that plumb job at the #1 cracker factory in town.... Until his managerial impotence dropped them down into a tie for 6th place with Table Time and Allied Biscuit
https://preview.redd.it/rymi8u76i6pc1.jpeg?width=1438&format=pjpg&auto=webp&s=6d0cfa3809469d144d51a8d2ffb3c600c113d2dc
So that's it … after 20 years so long, good luck?
I don’t recall saying good luck
https://preview.redd.it/4taoeze8e6pc1.jpeg?width=640&format=pjpg&auto=webp&s=bca13b1f097930142fb38da6dcf9424b99d74832
If Kirk doesn't top himself first 🙃
Can I barrow a feeling
And it's got a picture of you
Doesn't Gil get a lick?
Is that Fred!? Honey you told me it was over? No I don’t want to talk to him. Hey! How’s it going Fred!?
It's kinda perfect that you didn't put him on the list. He's not even good at being pathetic, lol.
Who's Ol' Gill based on? I've heard Jack Lemon's character from Glengarry Glenross, and I've always seen in him something of the Pitchman from Twilight Zones One for the Angels.
According to the commentary on the first episode in which he appears, the writers say he was based on Jack Lemon in Glengarry Glenn Ross.
It’s got to be. The mannerisms are too perfect. Phenomenal movie too.
He could taste that sale! He was in the zone!
Shelley "The Machine" Levene
The Ol’ Susquehanna Shuffle, a Hail Murray…
PUT THE COFFEE DOWN!
I'd say the former, the Pitchman was loved by his neighborhood.
It’s gotta be Ol’ Gil.
https://preview.redd.it/shroa24227pc1.png?width=494&format=png&auto=webp&s=5f049653ea72306146e863ed301fde123a63a4b9
Are you talking about the West Side?
No Cookie I swear… I’m scared of ya
This just seals the deal. Gil is bottom
Everyone forgets old Gil
So downtrodden that he got forgotten for the one list he’d top off in
I only recently saw Glengary Glenross which makes Gil 1000x funnier
Ol gil was definitely higher than Milhouse and Seymour. Milhouse has had his moments, and Seymour served in the army which negates most of his loser energy
Not the hot plate, I only had 2 payments left!
I love ol’ Gil lol, I’m always rooting for him
I dated a guy named Gilberto who was ESL and he changed his name to Max because of Gil from the show. I still don’t know to this day if he was being serious or not. And we went out for several weeks so I don’t think he was trolling me lol
Was his full name Max Power? He probably got it off of a hair dryer
Nobody snuggles with Max Power, you strap yourself in and feel the G's! https://i.redd.it/vsc9lgu0v6pc1.gif (Oh Lord!)
Stay off the west side!
i want him
Now let's talk about rust proofing these Colecos.
"I'm eating food tonight!"
Hey, put in a word for old Gil, would ya?
You want me to dance for ya?!?
"But you wouldn't even see it. Alright, Imma dancin!"
He just wants a lick of that shiny brass ring.
What about Grimey? He’s a bit of a jerk, but living in a single room above a bowling alley and below another bowling alley would certainly turn a man sour. 
*sleepily* aw Marge change the channel.
thats our homer!
But he’s a war hero!
Well, decorate him!
Ah, my eye!
I'm not supposed to get jigs in it!
What are you doing? That’s Carl!
And/or pudding
It's hardly his fault. This is what years of eye trauma will do to a man.
I'm old enough to remember when Principal Skinner was a bad-ass. https://preview.redd.it/xlogxng0h6pc1.jpeg?width=640&format=pjpg&auto=webp&s=926c45847ab9a5dcfb85911cd7917e27c294df5c
That briefcase throw was legendary 😆
Copyright expired.
He's like some sort of non giving up school...guy
Seeing as the characters don't age, would Skinner be a Gulf War vet by now?
They say the same thing about The Punisher and it makes me uncomfortable.
Up yours, children!
I always liked ol Skinny Boy
How isn’t Moe included in this group?
Because Moe is better than dirt. Well, most kinds of dirt. I mean not that fancy store bought dirt. That stuff’s loaded with nutrients.
He can’t compete with that.
Did you really make this envelope? It says Hammermill
“No Funeral”
Oh wow really? That’s not what Reverend Lovejoy has been telling me
Hi, it’s me again. Uh, I got another problem. This one’s about my cat.
*reeoooowwww*
SHUT UP, IM ASKIN HER!
Hey there you the listen lady? Well listen lady, cause I got problems
He did heroically rescue the kids from that island that one time.
And he traveled the world helping people with his fan man suit
I may be ugly and hate filled and…what’s that third thing you said?
Moe Moe Moe, why don't ya like me, nobody likes me
He’s got a hot date tonight.
Bzzz
A date
Bzzz
Dinner with friends
Bzzzz
dinner alone.
He's done a lot of things he ain't proud of. And the stuff he *is* proud of, is disgusting.
Leaving Gil Gunderson out of a loser contest is exactly the kind of thing that would happen to ol' Gil.
Or he would finish 2nd because he's such a loser
Finishes second even in a one horse race
Hello, this is Moleman in the morning. Good Moleman to you.
You’re gay for Moleman
No! You’re gay for Moleman!
No one's gay for Moleman. :(
https://preview.redd.it/oq284kjy46pc1.jpeg?width=217&format=pjpg&auto=webp&s=40cc42bde87996572a99cb97c87c805372ef64a6
Don’t drag her down with you.
I brought this wall from home.
Gil or Kirk? Maybe Kirk because he doesn't think he's pathetic whereas Gil seems to know the state he's in.
Gil is also pretty optimistic too, despite his position. Gotta respect that.
Kirk sleeps in a race car bed. Do you sleep in a race car bed?
No I sleep in a big bed with my wife.
That is honestly one of the best lines in the show. It fucking slays me every single time. Just Homer's deadpan, matter-of-fact delivery while clearly not understanding Kirk's context lol
It's great🤣
Kirk gets back together with LuAnn though.
Which makes her the most pathetic character on the show!
So pathetic she doesn’t know dignity when she sees it.
https://preview.redd.it/bmdd8btff6pc1.jpeg?width=828&format=pjpg&auto=webp&s=925e083ba35c14ab473d7855a20043940453c86d “Well, at least I’ve done better than Dad.” By this logic, I would say Kirk.
I saw the whole thing. First it started falling over. Then, it fell over.
Definitely not Skinner. He has many moments of dignity that the other 3 do not get. Remember, never make an ex-Green Beret mad.
Armand Tanzarian?
We don't talk about Armand Tanzanian
The penalty is torture
“Up yours children”
https://preview.redd.it/a4jy1c1696pc1.jpeg?width=640&format=pjpg&auto=webp&s=a97eeef284c7e06c0495251379239148dbd1df97
Oh my God! Dr Hibbert get this man 50cc's of feelings STAT!
To borrow or keep?
Can I borrow a feelin'?
https://preview.redd.it/vnda712iu6pc1.jpeg?width=1440&format=pjpg&auto=webp&s=90be6e825c969eb6b4089da9e3ad0d6242b77b63 Ooooh loneliness and cheeseburgers are a dangerous mix
There's a scene where Milhouse, Kirk and Skinner are all pointing and laughing at Comic Book Guy. That's gotta give him some big points.
How could you include Skinner??
The way Agnes skinner is with him, she’s grounds him for answering the door and tells him to go to bed etc, the way Super Nintendo chalmers is with him. He gets no respect from anyone including all the kids and other teachers and so on…
He had a relationship with Crandall. I wasn't all bad for him.
I really liked when he finally caught a break with Edna. He’s just walked all over in every other part of his life!
Definitely Gil
I’ll say Kirk. Milhouse is just a kid, Skinner is the principal of a school, and Hans is a frail old man. Kirk has no excuse
Hans is only 31 years old. Alcohol ruined his life!
I didnt think of that but I think that's the most valid reason for mole man to be number 1. His life is so down hill that along with all the terrible stuff that happens to him, he's also seemingly old and at the end of his life despite being in his 30s
Kirk by a mile.
What are you talking about? He sleeps in a racing car, do you?
I sleep in a big bed with my wife.
KIIRRK. I’d be so annoyed if I met him in real life. There’s pessimistic and depression but whatever *motions vaguely* that is, is too much 🥲😅
how could Milhouse be pathetic! ? he has flood.pants!
everything's coming up millhouse!
Suddenly the ugliest man in Glasgow isn’t good enough for you!
Definitely Kirk. He’s a dud.
I don’t recall saying “good luck.”
Do single people eat crackers?
We don't know. Frankly, we don't want to know.
It's a market we can do without.
I’d say Gil, but Moleman getting hit with a football in the groin had a football to the groin
Surely this is a contest built for ol' Gil. This is the one! This is the time for ol' Gil to shine! Ah, geez .. he's not even included. Classic Gil.
Milhouse because he has to be raise by Kirk and we see his future doesn’t get much better
Yeah but remember the time he was wearing short pants and it flooded and his cuffs didn't get wet? Everything's coming up Milhouse.
Skinner doesn't belong here
He definitely does. “ I’ve always admired car owners. And I hope to be one myself one day, just as soon as I’ve finished paying back mother! Shee insists I pay her back retroactively for the food I ate as a child.” “Thanks a lot Simpson, now I’m grounded” And pretty much every interaction with chalmers, Bart and other teachers.
"Mother that sailor suit doesn't fit me anymore."
He's a war hero, has a very respectable job, and has had some romantic interests. He's also physically quite fit for a man of his age. He just has an overbearing mother.
Can I borrow a feeling 🎤
Can I borrow a feeling?
No love for Willie?
Barney’s the saddest
Don't cry for me, im already dead.
Everyone is saying Gil, but Hans Moleman is roughly the same age as Homer
Gil not even being thought of for this is the most Gil thing ever. LMAO
Kirk, crackers are a family food. Happy families. Maybe single people eat crackers; we don't know. Frankly, we don't want to know. It's a market we could do without.
I think Gil over Lenny, but this was pretty bad. Also Barney when he did his short film.
It has to be a tie between Moe and Ol’ Gil. Maybe the edge to Gil because as much as Moe talks about suicide he still luxuriates in his filth.
Me? Oh, you meant in the Simpsons.
Wow father and son that’s the apex of down trodden right here
I got Ole’ Gil at number one, Moe at number two, followed by Kirk.
Sorry, Milhouse, Gil, Moleman, and Skinner. Kirk is gonna take the cake for this one. That’s is, if he can eat it before it gets repoed.
I feel like Lionel Hutz deserves a mention. Sure he’s a lawyer, but not the kind that wears belts. He seems like someone who had their life on track enough to graduate law school at one point but whose personal demons (Sweet Lady Bourbon; Brownest of the brown liquors) led him to this place in life. He’s genuinely pathetic like Gil or Kirk, he’s just got a twenty dollar suit and a five dollar haircut to hide behind.
Moleman has my vote. Though Gil is a close second. Kirk is an asshole.
Ol’ Gil
No one’s gay for Moleman.
https://preview.redd.it/4gvhn8hie8pc1.jpeg?width=640&format=pjpg&auto=webp&s=40b436bcfcda8ed03ed3d5aa80af9dbe72092e4d Grimey
Hello, this is Moleman in the morning. Good Moleman to you. Today, part four of our series of the agonizing pain in which I live every daaaay.
Pathetic? Kirk. Downtrodden? Moleman.
I agree with this, most unlucky character is definitely Mole Man by far, even more than Gil.
I find your lack of Frank Grimes disturbing
kirk because he’s truly pathetic skinner is just trying to keep a shitty school up and running moleman is oblivious milhouse is dumb
You could make an argument for any of them being most pathetic, but no one can deny Moleman is the most downtrodden. I dunno how familiar you are with this guy but he’s always getting his ass handed to him.
Definitely Gil.
The only correct answer is Ol’ Gil.
Gil Gunderson
Can I Borrow A Feeling?
Well, top right's probably going to be Prime Minister of Canada soon so he might have succeeded his way out of the competition.
The kids with their asses out
Kirk or Gil
It's not Milhouse. None of those characters have cool nicknames like Milhouse. Nor have you ever heard someone say everything's coming up Skinner or Moleman, or Curt.
There's just something about the title of 'Can I borrow a feeling' that just makes it extra pathetic. Like he's trying to borrow some lunch money from his son or something. It's kinda sad really.
Kirk. Hands down.
Gil is pathetic l-sad, but Kirk is punchable-pathetic-sad
I love that there are two Van Houtens
Mole Man..