I think we have the top three.
Thank you so much for linking to this. I knew a few Kliban cartoons but had never seen this one. It’s just wonderful.
We don’t know. We never know. One cannot ‘explain’ a Thurber drawing. They just… are.
That’s a John Caldwell cartoon.
Another one I love of his is this. Pure non sequitur
A man is lying in the street in some sort of medical distress. The caption is “Everybody back! This man has swallowed his nose! Don’t panic, I’m a sheet metal worker. Someone bring me a pail of water and a catcher’s mitt.”
There’s also his “Society of Retired Comedy Writers,” which shows someone outside its door saying “Knock, knock.”
Perhaps my favourite Kliban cartoon:
‘Cleopatra committed suicide by holding a beast to her ass.’
The caption describes the image.
Another fave depicts a disappointed-looking boy entering a house. An old woman is seated at a table shoving a porcupine head-first into her mouth, while another porcupine stands on the table. ‘By the time I got home, Grandmother had eaten most of the porcupines.’
I have Whack Your Porcupine, Cat, Never Eat Anything Bigger Than Your Head, Tiny Footprints, and Two Guys Fooling Around with the Moon. Many of his cartoons are brilliant. Some are just weird. I wish more of his work was online, as I can’t tell you how often I’ve wanted to share.
Sam Gross.
My older BIL gave me his books when I was about 13 or so.
I think I remember his cartoons being sprinkled throughout the Playboys of the time.
I remember thinking they were the funniest things I’d ever seen.
Another Kliban I’ve remembered:
A dejected-looking man is walking along the street, and he sees another man severely abusing a woman. The dejected man says, ‘I wish I had a girl.’
I currently like xkcd
BTW, catch the Calvin and Hobbes reference in frames 9 and 10? Another great cartoon.
IIRC, a Mad Magazine parody of Family Circus. Billy is showing his pet turtle to the family…
“My turtle’s all gnarled and smelly, just like Grandma!”
Gahan Wilson had some really good ones.
Two wealthy old biddies strolling down the street in their furs and pearls see a hideously deformed creature (drawing hideous deformity is one of GWs strengths) pursued by another bizarre creature that’s practically all teeth. The first woman says to her friend, “It’s just one damned thing after another.”
Truck stop in a bare, flat wasteland. Only the counter person and one lonely trucker are inside. Atop the small, well-lit, glass-walled restaurant is a huge neon sign that says “EAT.” In the distance, a mind-bogglingly vast creature with a mouth to match is literally crawling over the horizon, drooling, heading straight for the truck stop. One of the two (the counter person, maybe?) says in alarm, “MY GOD, do you suppose it can READ?”
Another New Yorker. This absolutely broke me up - Peter Pan’s cousin.
A few of my favorites I couldn’t find online, but they’re all in one of those books up there^.
Man, I gotta dig out my Kliban books (I have all of those as well) when I get home!
Ear Muffs! Inglese! “No hay telephonos, Gringo Pendejo!” The ocean that proved to be inaccessible! The psychedelic muffin! I love it!
Another NatLamp toon: A waiter, with a triumphant grin, takes the cover off the dish he is presenting a diner: “It’s a fried telephone book! We gave it a fancy French name and you ordered it!”
I have always loved Sergio Aragones ‘marginals’, the tiny cartoons that were liberally sprinkled through almost every issue of mad magazine.
Thurber himself was asked this. Typically, he answered: “well, I’ve just asked my taxidermist and he says you can’t get a person stuffed …”. IOW he didn’t know either.
No love for Gluyas Williams?
I won’t say any more yet because it’s more fun if there’s at least one other Gluyas Williams fan to babble with.

Two wealthy old biddies strolling down the street in their furs and pearls see a hideously deformed creature (drawing hideous deformity is one of GWs strengths) pursued by another bizarre creature that’s practically all teeth. The first woman says to her friend, “It’s just one damned thing after another.”
That’s the first Gahan Wilson cartoon I always think of when I think of Gahan Wilson cartoons.

I have an original copy of Never Eat Anything Bigger than Your Head.

Another NatLamp toon: A waiter, with a triumphant grin, takes the cover off the dish he is presenting a diner: “It’s a fried telephone book! We gave it a fancy French name and you ordered it!”
I had this one on my dorm room wall. Thanks for adding it.

Kliban once called that his favorite of all his cartoons. I would have mentioned it, but it’s impossible to describe (or to explain why it’s so funny).
Kimstu, I wouldn’t say I’m a fan of Gluyas Williams, but he did a few truly great ones (the crisis as Proctor and Gamble, and Mr. Coolidge refuses to leave the White House). From that era, though, I’m partial to Peter Arno, including this, which seems to have introduced a catchphrase we’re still using today.