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Some of the funniest moments in life are the ones that seem completely ordinary until someone points out just how strange they really are. Conversations with a partner, office meetings, vacations, commutes, and even attempts to relax can suddenly look ridiculous when viewed from the right angle.

Cartoonist David Sipress has spent decades finding humor in exactly those moments. Since his first cartoon appeared in The New Yorker in 1998, his single-panel work has explored relationships, work, culture, politics, anxiety, and the many peculiar ways people try to navigate everyday life. We’ve featured Sipress’ cartoons several times before, and today we’re back with another selection of his sharp observations and understated punchlines.

We also reached out to him to learn a bit more about his work, so scroll down to read the short interview and enjoy the latest collection of comics.

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

This post may include affiliate links.

#1

A New Yorker cartoon showing a presenter on stage with a screen reading I Am A Genius during a TED Talk

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David Paterson
David Paterson
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1 hour ago

Which reminds me ... I need to give a Ted Talk.

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    #2

    New Yorker style cartoon showing a traffic jam next to a road sign reading Schadenfreude.

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    #3

    New Yorker cartoon with a sweaty, disheveled woman entering an apartment while a man reads on the couch.

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    #4

    A grim reaper New Yorker cartoon checking his watch while talking to a man at his door.

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    #5

    A black and white cartoon depicting soldiers with a Trojan horse with a witty New Yorker caption.

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    #6

    A black and white cartoon showing a man in shorts and sandals at home, a New Yorker style drawing.

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    #7

    A black and white cartoon of Roman soldiers negotiating a trade, showcasing New Yorker humor.

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    #8

    New Yorker veteran cartoon of a fortune teller predicting a hilariously bad travel experience.

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    #9

    A New Yorker veteran cartoon of a man grilling an alien monster for a child

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    #10

    A New Yorker veteran cartoon showing an advisor flattering a president at his desk

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    David Paterson
    David Paterson
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    1 hour ago

    Is that Mike Pence on the left? It didn't save him.

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    #11

    A New Yorker veteran cartoon with a man and woman playing tennis on a court

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    #12

    A New Yorker veteran cartoon of a mermaid on a beach talking to a centaur

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    LakotaWolf (she/her)
    LakotaWolf (she/her)
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    Premium     53 minutes ago

    If they got together and had a baby, would it be a mer-hippocampus? XD

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    #13

    A New Yorker veteran cartoon showing Mayan people discussing a ball game in front of a temple

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    #14

    A New Yorker cartoon depicting a meditation class on a journey to enlightenment with someone asking are we there yet

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    #15

    A New Yorker veteran cartoon depicting a woman looking at the last handwritten thank you note in a museum

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    #16

    A New Yorker cartoon depicting a fortune teller and an ancient Greek soldier with a Trojan horse.

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    #17

    A black and white cartoon of devils pointing people to a beach with a funny caption about New Yorker life.

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    #18

    A New Yorker cartoon featuring a man bringing a pile of books to a woman on a couch for National Poetry Month

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    LakotaWolf (she/her)
    LakotaWolf (she/her)
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    Premium     51 minutes ago

    I'm an English major with a degree in English/Creative Writing, and I personally think most poetry is insufferable XD That being said, there are some truly brilliant poets out there who wrote awesome poetry - Robert Frost, Rudyard Kipling ("The Power of the Dog" will break you), T. S. Eliot ("The Waste Land"), Lord Byron, John Keats, W.B. Yeats, Stephen Dobyns, just to name a very few. But a lot of poets are also totally inscrutable X'D

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    #19

    A New Yorker cartoon showing two men in pajamas looking at each other as one says he is from the future

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    #20

    A New Yorker veteran cartoon showing people leaving a theater after a play

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    #21

    A New Yorker veteran cartoon of football players thinking about injuries before a tackle

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    #22

    A New Yorker veteran cartoon depicting a woman asking a man about the philosophical meaning of nothing

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    LakotaWolf (she/her)
    LakotaWolf (she/her)
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    Premium     50 minutes ago

    All of the above! XD

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    #23

    A New Yorker cartoon depicting two men in suits discussing compassion fatigue next to a beggar on the street

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    #24

    A black and white cartoon of two people at a beach bar with a humorous caption about being a New Yorker.

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    #25

    A New Yorker veteran cartoon depicting a man grilling on Labor Day with a child watching

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    #26

    A New Yorker veteran cartoon showing a teacher leading classroom students reciting the pledge of allegiance

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    More from this series:
    Previous · Part 3 A Longtime New Yorker Cartoonist Captures The Strange Logic Of Everyday Life (24 New Pics) Previous
    All 4 parts All 4 parts in this series
    1This Cartoonist Makes Single-Panel Comics That Are Both Absurd And Relatable (66 Pics) 225 Everyday Moments That Become Brilliantly Awkward In David Sipress Cartoons 3A Longtime New Yorker Cartoonist Captures The Strange Logic Of Everyday Life (24 New Pics)
    4 You’re here26 New Brilliant Cartoons By A New Yorker Veteran That Expose The Absurdity Of Everyday Life
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