Oliver Perry's charming illustrations recreate the magic of vintage New Yorker cartoons

Sometimes classic cartoons can feel like they're depicting a world from another dimension, and perhaps this is most evident with somewhere as famous as New York City. In olden-time illustrations, things like the buildings can look familiar, but the penmanship and detailing evoke a completely different environment.

But what would it look like if the past caught up with the present? How would the trappings of modern life appear if they were expertly drawn in the pen and ink stylings of yesteryear? That's exactly what Oliver Perry captures in his delightfully whimsical illustrations of everything from a dog in an Ikea bag on the subway to a pair of musicians playing in Washington Square Park.

A lifelong illustrator who began by honing his drawing skills in high school before pursuing it professionally, Oliver has gone on to work with the likes of Puma, Cricket Magazine and the Society of Illustrators. His work has even appeared on Link NYC kiosks dotted around the city.

Inspired by illustrative styles and storytelling from across print and film, Oliver's style was further polished at the School of Visual Arts, NYC, where he earned a BRA in Illustration with High Honours. But in terms of influences, it's fair to say that nothing rivals the cartoons found in the yellowing pages of classic magazines.

"I love looking through vintage art books, vintage New Yorker Cartoons, and their magazine covers," Oliver tells Creative Boom. "The vintage New Yorker Magazine's pure spontaneity is magical and creatively inspiring. In a world filled with digital and A.I., I sincerely appreciate the perfectly imperfect nature of authentic hand-drawn illustrations."

Described by admirers as whimsical and charming, Oliver's work is also driven by his love of illustrating stories, "particularly humorous ones." This is clearly evident in his drawings, where a dog shakes itself dry next to a man trying to eat or a woman resting on a sun lounger as a race goes on behind her. "Expressions and characters are a vital part of my work."

It's not just all whimsy and New York life, though. One of Oliver's most notable recent projects emerged from the pandemic and was selected for The New York Historical Society Covid-19 Collection. "I had the honour and privilege of submitting a watercolour painting of Captain Sir Thomas Moore, who, at 100 years of age, raised nearly 33 million pounds for Covid-19 relief," Oliver explains.

"The New York Historical Society selected the painting as part of their Covid-19 Collection, which will hopefully be on exhibit one day."

When he's not working, Oliver keeps his skills sharp by drawing from life. "I love to visit and immerse myself in outdoor New York City locations because, like a workout at the gym, it continuously improves my hand-eye coordination.

"I am often attracted to the daily eccentricities at Washington Square Park. There, on any given day, I can surround myself with an array of subject matter - from street performers and animals to creative influencers and musicians, often dressed in one-of-a-kind fashions. I relish the challenge of capturing the unique energy drawn from real life."

Aside from drawing, Oliver is also a practising magician. And while the two might sound like separate passions, they have a curious overlap. "Both illustrating and the 'art' of magic require tremendous practice, dedication, and hand-eye coordination," he reveals.

"I enjoy the serenity I find in illustrating, but I also love performing for audiences who readily show their appreciation."