20 Best Humor Cartoons by David Ostow That Fans Absolutely Love

May 6, 2025

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Best Humor Cartoons is exactly what this comic review is all about—and we’re spotlighting none other than the brilliantly witty mind of David Ostow. If you like your comics clever, quirky, and just a little unhinged (in the best way), you’re in for a treat. This article dives into 20 of David Ostow’s finest works, each packed with that special combo of wordplay, cultural commentary, and “did he really just go there?” humor.

David Ostow is a Brooklyn-based cartoonist known for his sharply satirical illustrations and instantly recognizable hand-drawn style. His work has been featured in major outlets like The New Yorker and McSweeney’s, and he’s built a fanbase drawn to his unapologetically smart and socially observant humor. What sets Ostow apart is his minimalistic yet expressive art style and his ability to turn ordinary scenarios into deadpan brilliance. He often explores themes of modern culture, technology, family dynamics, and the surreal side of city life. Each cartoon feels like a well-written one-liner that happens to come with a punchy drawing.

The best humor cartoons, David Ostow style.

#1 The Lifestyle Trends of Cavemen

Two cavemen critique ancient art while complaining about “another new lifestyle trend.” The juxtaposition of prehistoric visuals with today’s obsession with trends makes this comic a hilarious commentary on consumer culture. Ostow pulls off the joke with such casual irony, you’ll wish your own wall art talked back.

#2 Encouraging the Wrong Deer

A cloaked deer cheers on another as it hesitates in the middle of the road. “Go for it!” he says—moments before disaster, presumably. This cartoon takes motivational clichés and mercilessly flips them into situational comedy. Dark, but not too dark—just how we like it.

#3 Mom Rankings: Participation Trophy Edition

Busts of different moms are ranked from “Best” to “Just Okay,” ending with a “Participation Certificate” for the mom of a mansplainer. It’s a perfect roast of judgment culture and family dynamics, all wrapped in a tidy row of stone-carved sarcasm.

#4 Credit Card Caution on Mother’s Day

As kids surprise their mom with breakfast and flowers, she casually warns them not to check the credit card bill. Ostow nails the emotional manipulation that comes with gift-giving seasons, making us laugh while also side-eyeing our bank statements.

#5 Quartet or Haircut?

A barbershop quartet breaks into song, much to the confusion of customers just wanting a trim. This comic is for anyone who’s ever endured unnecessary theatrics while just trying to get stuff done. Relatable, ridiculous, and perfectly awkward.

#6 The Praying Mantis Breakup

A praying mantis casually mentions being glad things didn’t get serious—because, well, we know what happens post-mating. Ostow fuses entomology with dating horror stories to create something darkly delightful. One of his best relationship jokes to date.

#7 Buses and Their Emissions Diet

Three city buses sit parked like old friends, discussing their “clean eating” goals. The anthropomorphic twist is both charming and hilarious—a subtle jab at environmental bandwagoning and our never-ending obsession with health trends.

#8 Escape Room Therapy

A family prepares to unwind in an “escape room” located in a back alley. This cartoon hits the absurd nail on the head—are we escaping stress by simulating more stress? With a setting this gritty, Ostow asks the question while letting the visual answer it.

#9 Local Cafe Identity Crisis

A tourist family works on logo designs in a neighborhood coffee shop, pretending to be “experiencing the local vibe.” It’s a snide, funny take on gentrification and digital nomad culture, served with a double shot of irony.

#10 Celestial Indifference

An angel relaxes with a smoothie while Earth burns behind him. His shirt reads “All Planets Matter.” It’s one of Ostow’s sharpest and darkest political cartoons—calling out performative allyship with brutal precision.

#11 The Realtor From Space

An astronaut pitches Mars real estate as “cheaper than Brooklyn.” Ostow blends real-world frustration with sci-fi absurdity, making us chuckle at housing crises from here to the cosmos.

#12 Divine Accounting Woes

A Jesus-like figure is chastised by an accountant for filing late. This cartoon hilariously merges sacred themes with mundane red tape. Perfect for anyone who’s ever missed a deadline—and had to explain it to upper management.

#13 Dinosaur Birthday Party Confusion

A kid asks if the birthday party is BYOD—Bring Your Own Dinosaur. The confusion is as adorable as it is absurd, and the expression on the parent’s face makes the punchline land beautifully.

#14 …Has Left the Group Chat

A tombstone bearing the epitaph “…has left the group chat” is dark humor at its finest. It’s a hilarious and haunting commentary on how digital language has seeped into everything—including death.

#15 Family Venn Diagram Breakdown

A couple made of literal Venn diagram circles complains that their only overlap is their child. Ostow turns emotional distance into geometry and somehow makes it hilarious. Easily one of his smartest visual metaphors.

#16 Non-Stick Spray for Pastries

Toaster pastries discuss spa treatments involving cooking spray. Yes, it’s as weird and funny as it sounds. Anthropomorphic breakfast food and wellness culture? Only Ostow could merge the two so seamlessly.

#17 The Hard Truth About Hustle Culture

A businessman proudly tells a child he’ll never work a day in his life—as long as he works nonstop at everything else. The strip is a masterclass in satire, taking down toxic productivity in one line.

#18 Martian Earth Day Irony

Astronauts stroll across Mars, commemorating “Earth Day.” The gag here is both smart and unsettling. It’s a joke that looks forward while asking what exactly we’ve left behind.

#19 Pretentious Bedtime Greek

A parent insists on reading a children’s bedtime story “in the original Greek.” It’s a delicious jab at intellectual pretension and parenting competitiveness. Also, great for fans of overachievers.

#20 Couples Therapy Bombshel

A therapist observes that the real issue isn’t how a word was pronounced—but the cheating. The cartoon’s punchline is blunt, hilarious, and utterly relatable. Couples therapy never looked so entertaining.

Final Thoughts: A Perfect Dose of Wit and Absurdity

If you’re hunting for the Best Humor Cartoons, David Ostow should be at the top of your list. His work effortlessly blends laugh-out-loud absurdity with razor-sharp commentary, all wrapped up in a style that’s refreshingly minimal yet expressive. Each cartoon gives you something to smile at—and something to think about.

Whether you’re here for the laughs or the insight (or both), these 20 comics by Ostow are some of the best you’ll find in the modern humor scene.

Credit to the Artist

All cartoons featured here are the brilliant creations of David Ostow, a cartoonist with a talent for balancing wit, art, and cultural critique. His distinct drawing style and clever voice make his work unforgettable.

Explore more of his cartoons here:

And for more hilarious comics from creators like Ostow, visit 👉 Boredcomics.com