David Ostow comics hit that rare sweet spot between smart and silly, holding up a funhouse mirror to our everyday chaos. Whether he’s poking fun at astrology, generational quirks, or the bleak beauty of digital hell, Ostow’s wit is dry, his timing impeccable, and his characters hilariously human (or not-so-human). If you love comics that make you snort-laugh and think at the same time, you’re in for a treat.
About the Artist: David Ostow
David Ostow is a Brooklyn-based cartoonist known for his clever, socially attuned humor and bold, expressive illustration style. A frequent contributor to The New Yorker, Ostow combines pop culture references, millennial dread, and classic observational comedy in a way that feels sharp but never mean-spirited. He has a knack for turning life’s oddities into punchlines that land hard and linger longer. Whether it’s through single-panel gags or quietly devastating commentary on modern life, his cartoons always feel timely, relatable, and refreshingly original. From therapist couches to Tinder tables, Ostow draws what we’re all thinking but rarely say. And somehow, he always manages to make it funny.
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1. The Most Millennial Breakup Ever
This comic perfectly captures the modern dating scene in all its astrological, pop-culture-obsessed glory. When the woman begins her breakup speech with a blend of zodiac signs, Hogwarts house affiliation, and a Sex and the City identity, it’s clear this isn’t your average “it’s not you, it’s me” moment. Ostow nails the way millennials overanalyze and over-identify to the point of absurdity. It’s a hilarious nod to how we sometimes replace emotional depth with personality quizzes.
2. Motivated by Grounding
Grounding a child has never resulted in such an unexpected response. In this comic, a young girl dramatically declares that without her phone, she’ll have no choice but to become a world-class violinist. The mix of parental panic and resignation in their expressions is spot-on. It hilariously skewers modern parenting, tech dependence, and the ironic ways kids try to guilt-trip their way out of consequences—by aiming for overachiever status.
3. Therapy Meets Sisyphus
In this intellectual gem, Ostow drops us into Greek mythology with a modern twist. As Sisyphus endlessly pushes his boulder uphill, a therapist nearby gently questions the concept of “reaching the top.” It’s darkly funny and uncomfortably accurate, especially for anyone stuck in the loop of modern hustle culture. With just a few lines, Ostow turns ancient tragedy into modern malaise, all while delivering a joke that feels both profound and punchy.
4. Founding Fathers & Safe Words
Two researchers comb through dusty legal tomes and historical texts, only to discover a glaring omission—not a single safe word in the nation’s founding documents. The visual setup is mundane, but the punchline lands hard. Ostow’s ability to combine legal jargon with modern sexual humor creates a comic that feels both daring and deadpan. It’s a pitch-perfect jab at the way we hold historical texts sacred while ignoring how culture evolves.
5. Hell is Other Photos
In this devilishly clever comic, a demon guides two poor souls through a fiery underworld—straight to the eternal punishment of organizing every digital photo they’ve ever taken. It’s a nightmare scenario that taps directly into 21st-century chaos. Ostow blends surrealism with tech anxiety, highlighting how even mundane modern tasks can feel like their own personal hell. It’s equal parts funny and frightening—especially if your phone’s gallery is a mess.
6. Reading for Guilt
A woman cheerfully admits that she always packs a book not to read it, but to feel properly guilty about not reading. It’s a sharp jab at self-improvement culture and our obsession with productivity. Ostow exposes the hilarity in our contradictions—wanting to be better while actively avoiding the effort. With simple lines and dry humor, he turns a relatable internal struggle into a single-panel masterpiece of modern procrastination.
7. Spider Confessions
What starts as an innocent date quickly turns into a silent horror show. A woman sheepishly says she doesn’t want to bore her date with spider talk, while behind her, the room is covered in webs and crawling with spiders. It’s a perfect contrast of restraint versus reality. Ostow nails the art of the visual punchline, showing us how people downplay major chaos in an effort to appear chill.
8. Mob Meeting, Animal Style
A rat, a cockroach, and a pigeon sit at a mob-style roundtable discussing city domination. It’s a scene straight out of The Godfather, reimagined with urban pests. The absurdity of the image clashes hilariously with the seriousness of the dialogue. Ostow taps into the darker side of city living and flips it into a ridiculous fantasy, proving that even rodents can organize when the stakes are high.
9. Duck Union Demands
On a peaceful farm, a duck tells its human boss it’s time for a break after tirelessly quacking all over the place. It’s a delightful take on labor rights with a barnyard twist. Ostow’s anthropomorphic humor shines as he transforms a cute farm animal into a disgruntled employee. The comic hilariously echoes real-world worker burnout in the most feathered, charming way.
10. Cosmic Parenting Advice
This dad lays down some generational wisdom with a twist: he urges his son to make the exact opposite mistakes he did, starting an endless yo-yo of overcorrections. The metaphor is poetic and hilariously accurate. Ostow takes a simple parent-child interaction and turns it into a profound (and funny) commentary on how families unintentionally swing between extremes. It’s relatable, clever, and sneakily philosophical.
Final Summary
David Ostow comics blend brainy satire and absurdist humor to capture our collective neuroses. With just a single panel, he reveals the punchlines hiding in our daily lives—whether it’s a duck asking for PTO or a violinist-in-training rebelling against screen time rules. Ostow’s work is as funny as it is sharp, balancing commentary with charm. It’s no surprise his cartoons have become favorites for anyone trying to laugh through the nonsense of modern life. All artwork by David Ostow. For more, visit TheHumorSide.com.
