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.
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#1
Image source: dsipress
When we asked Sipress where his ideas tend to come from, he explained: “My ideas are rooted in my everyday experiences, and they are the result of my constantly asking myself if there is a cartoon in those experiences. Imagination is, of course, a part of the process; it’s what transforms observations into art.”
#2
Image source: dsipress
#3
Image source: dsipress
That ability to recognize something familiar in an otherwise absurd situation is a big part of his comics’ appeal. His cartoons can move effortlessly between relationships, office life, sports, literature, history, and existential worries, often treating the most ridiculous premises with complete seriousness.
#4
Image source: dsipress
#5
Image source: dsipress
Asked whether he can tell when an idea might make readers think, “That’s so me,” Sipress said his approach is much more personal. “I only ever think about what is ‘so me’—myself, that is—and I’ve learned to trust that what is ‘so me’ will also be ‘so me’ to my readers.”
#6
Image source: dsipress
#7
Image source: dsipress
There is also something particularly effective about how simple Sipress’ cartoons are. A few loose black lines establish the situation, while a short line of dialogue or a single caption delivers the joke. Sometimes the punchline lands immediately; other times, the reference takes an extra second to click.
#8
Image source: dsipress
#9
Image source: dsipress
When we asked which everyday human behaviors continue to inspire him after so many years of making comics, Sipress singled out one especially reliable source of material. “There are many human behaviors that inspire my cartoons, but if I have to pick one, I would say I am keenly interested in worry and the many ways worrying defines who people are – myself in particular.”
#10
Image source: dsipress
#11
Image source: dsipress
That interest makes sense in a body of work so often centered on how people think, react, overanalyze, misunderstand one another, and try to make sense of situations they cannot completely control. Even when the scenario is wildly unrealistic, the emotion underneath it is often recognizable.
#12
Image source: dsipress
#13
Image source: dsipress
With hundreds of cartoons published in The New Yorker and decades spent observing human behavior, Sipress has found no shortage of material in people’s habits, contradictions, anxieties, relationships, and egos. And despite how differently readers can approach humor, he told us: “I can’t recall a cartoon being interpreted differently from what I intended.” Clarity in intention and message. The situations may be absurd, but the behavior behind them rarely is, and that small gap between the ridiculous and the recognizable is where Sipress continues to find plenty to laugh about.
#14
Image source: dsipress
#15
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#16
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#17
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#18
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#19
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#20
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#21
Image source: dsipress
#22
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#23
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#24
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#25
Image source: dsipress
#26
Image source: dsipress
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