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If you’ve ever walked away from a family gathering thinking “Well, that felt… weird,” or sat through a polite conversation that somehow felt like a small-scale hostage situation, David Sipress’ cartoons will feel uncomfortably familiar.

Sipress highlights the absurdity, contradictions, and discomfort that we all experience in our lives by amplifying the absurdity of everyday situations to the maximumlittle social misfires, forced smiles, and the kind of blunt honesty that slips out right after someone says, “So anyway…” His work is visually simple, but the socio-cultural and political discussions underlying the punchlines are far from that.

A dinner table becomes a diplomatic crisis. A routine checkup turns into a moment of clarity nobody asked for. Couples negotiate the unspoken rules of long relationships, coworkers stumble through office etiquette, and holiday traditions unravel in real time. Even when the setup is absurd, the emotional logic is painfully real, which is why the punch lands.

A big part of the appeal is that even when the jokes are painfully obvious, they invite a level of contextual knowledge of the world and current events for one to be able to fully grasp the implications. This makes sense when you realize Sipress has been honing this observational style for decades, including a long run at The New Yorker, where his cartoons have become a go-to snapshot of everyday social and political friction.

And if you’re curious how a mind like this gets built, Sipress’ memoir What’s So Funny? offers some context without spoiling the magic. But the cartoons are the main event. They’re the kind of funny that makes you laugh first, then wince a second later, because you’ve absolutely been there.

You can learn more about Sipress on his website and check out more of his cartoons on his Instagram page.

More info: Instagram | davidsipress.com | Facebook | x.com

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    #2

    New Yorker cartoon by David Sipress showing a woman watching TV news with a sarcastic top story caption.

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    Lotekguy
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That ain't news, brother. That's business as usual.

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    #4

    New Yorker cartoon by David Sipress showing a bird talking to a Twitter logo on a tree branch.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I got onboard Twitter early in the game. Even attempted to stick with it after that disgusting nitwit took it over since I really enjoyed many of the posts. But that was then and this is now, and I can't visit that site any longer.

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    #5

    Black and white New Yorker cartoon by David Sipress showing a couple watching a news anchor saying no news is good news.

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    Kelly H. Wilder
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That one night the BBC had nothing to report so played music instead

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    #7

    New Yorker cartoon by David Sipress showing a man working on a laptop while a woman relaxes outside on vacation.

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    Bill Swallow
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "No, I'm just going to relax and enjoy myself the entire vacation - AND after I get *back* from vacation!"

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    #10

    Black and white New Yorker cartoon by David Sipress showing medieval king and guards with caption about science and personal taste.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Ayep. Plenty of red meat and whole fat milk. I'm 100% onboard with removing processed and ultra-processed foods from our diets, but flipping the food pyramid is beyond ridiculous - it's dangerous. Same age as that dingbat RFK jr. but I don't look like a used saddle bag that's been left out in the sun.

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    #11

    New Yorker cartoon by David Sipress showing two people picking up dog waste on a city sidewalk near a car.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    A few of my cats would watch me clean the litter boxes, then promptly use them. Their unique way of showing appreciation.

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    #13

    New Yorker cartoon by David Sipress showing a woman practicing yoga balancing on one foot in front of a mirror.

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    Bill Swallow
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    The cat is wondering if she's about to fall on him.

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    #15

    Black and white New Yorker cartoon by David Sipress showing a woman and child sitting indoors with humorous caption about worrying what others think.

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    Lotekguy
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    My parents passed away many years ago, but their voices are still in my head.

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    #19

    New Yorker cartoon by David Sipress showing a family at Thanksgiving with humorous disagreement around the table.

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    Multa Nocte
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Yeah, this past year in the US has been kind of suck.

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    #20

    New Yorker cartoon by David Sipress showing a doctor explaining different types of cholesterol to a patient in an exam room.

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    Auntriarch
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I have no idea why I find this so chortlesome

    #23

    New Yorker cartoon by David Sipress showing three figures watching television in a messy room with a humorous caption.

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    Rusty’scate
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    How it started in 2024 and how it’s going in 2026.

    #25

    New Yorker cartoon by David Sipress featuring a humorous office scene about a proposal for an idea concept.

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    David Paterson
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    It's a sketch for a proposal about an idea for a concept.

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    #26

    New Yorker cartoon by David Sipress showing a man with planets around him claiming to be the center of the universe.

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    Janissary35680
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    1 day ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    Since the visible universe is isotropic, he's correct.

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    #28

    New Yorker cartoon by David Sipress showing wolves howling at the moon with the caption about the pointlessness of art.

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    Bill Swallow
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Something just seems so ... wrong ... about a pack of wolves singing *barbershop*.

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    #29

    Cartoon by David Sipress showing a dog playing dead and then happily playing guitar, featuring New Yorker humor.

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    Multa Nocte
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    🎶 Casey Jones you better, watch your speed 🎶

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    #32

    New Yorker cartoon by David Sipress shows a man in pajamas asking if anything bad happened as a woman pours coffee.

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    Auntriarch
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    1 day ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    My brother in law's phone bingled a news alert last week, my sister in law and I simultaneously said "oh god what's he done now"

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    #41

    Man watching New Yorker cartoon on TV by David Sipress showing a protester with a sign saying the end is near.

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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Just another whacko predicting climate change and the death of the planet. /s

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    #43

    New Yorker cartoon by David Sipress showing a man in a suit with GET hat passing a woman ringing a bell by a GIVE box.

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    Lotekguy
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    If this were in color, the wrong one would be wearing red.

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    #46

    New Yorker cartoon by David Sipress showing Atlas holding the world with two onlookers commenting on steroids.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    If he was on steroids, he wouldn't need such a large loin cloth.

    #47

    Black and white New Yorker cartoon by David Sipress depicting a family raising glasses at a dinner table with a turkey.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Pre-Thanksgiving, everyone in the building was chatting about celebrating the holiday. But since this was my attitude, I stayed home and enjoyed my delicious meal in peace.

    #48

    New Yorker cartoon by David Sipress showing a man pouring wine from a giraffe shaped carafe at a dinner table.

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    Dave Nalesnik
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Actually, the way things are going...just leave the giraffe.

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    #50

    Man watching a New Yorker cartoon by David Sipress on TV with a humorous news caption about a former President.

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    Bill Swallow
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Yeah, well, Beelzebub ain't exactly bragging about knowing YOU, Donnie!

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    #51

    Two people and a cat thinking repeatedly about the election and a liver feast in a New Yorker cartoon by David Sipress.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I try to think like a cat, but reality keeps sneaking in.

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    #54

    Cavepeople discussing art world indifference with humorous New Yorker cartoons by David Sipress in a prehistoric setting.

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    Janissary35680
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    IMAGE: artist's impression of what wooly mammoths may have looked like

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    Black and white New Yorker cartoon by David Sipress showing a man watching TV and commenting on the Yankees not playing in the post-season.

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    Lotekguy
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Bostonian schadenfreude.

    #57

    New Yorker cartoon by David Sipress showing a boat full of people approaching a tunnel labeled next three weeks.

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    Ryan Mercer
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Getting wet will be the least of your worries.

    #58

    New Yorker cartoon by David Sipress showing a man sunbathing under an umbrella with a woman telling him to get up.

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    WindySwede
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "Wake me up when September ends" 🎵

    #60

    New Yorker cartoon by David Sipress shows a cat performing comedy in front of a seated couple in a living room.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Typical cat, always upping the entertainment antics.

    #61

    New Yorker cartoon by David Sipress showing a woman with demons outside a café discussing taking a lunch break.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I hadn't scroll far enough to see the script, so my immediate thought - it's about a mother and her spawn in public.

    #63

    Two castaways on a tiny island with a palm tree, New Yorker cartoons by David Sipress capturing humor and isolation.

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    Riley Quinn
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    1 day ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Pretty much what I did. It was so peaceful that day.

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