Portrait of an Artist – Caricaturist David Cowles

Left: The Beatles, created in the 1980s; Right: Stevie Wonder - Created for the NAACP Image Awards and presented to Wonder in 2008
by Nancy E. McCarthy

Rochester artist David Cowles has enjoyed a robust and distinguished 40-year career as a caricaturist and illustrator. Cowles’ colorful caricatures have appeared in numerous publications such as Time, People, The New York Times, Chicago Tribune and Vanity Fair. His commissions include posters, album covers and advertisements plus his signature caricature portraits hang in homes here and abroad. More recently, Cowles’ illustrations have come to life in animated projects for Disney, Sesame Street and the rock band They Might Be Giants among others.

Caricatures originated in Italy in the 16th century. Then and now, these drawings capture the likeness of an individual by emphasizing or exaggerating the specific features which makes a person unique. Elements of whimsy, humor or satire are infused into the representation.

Cowles’ interest in caricature started with the irreverent comic book MAD magazine. 

“I always loved MAD magazine as a kid and was particularly into the caricatures Mort Drucker did in the movie and TV parodies in there,” said Cowles. “I tried my best to draw like him up through high school.” 

He then discovered Al Hirschfeld. Hirschfeld’s minimalist approach (most notably drawing black and white caricatures of Broadway stars) was the opposite of Drucker’s highly detailed drawings. Back in 1924, Hirschfeld shared a studio with the renowned Mexican caricaturist Miguel Covarrubias (1904-1957) and was influenced by his linear style. Covarrubias was Cowles’ main inspiration when he began his own art career. 

Artistic genes

Cowles, the youngest of six siblings, was born in Rochester in 1961. His father, Hobart, was a Rochester Institute of Technology ceramics professor and his mother, Barbara, managed a crafts gift shop. 

“Art was the family business,” said Cowles. “I drew as soon as I was able, and both parents were very supportive of my interest in it.”

After high school, Cowles enrolled at Graphic Careers to learn about the advertising business. He met his future wife Laura Wilder there. When they married in 1985, Cowles was on the Democrat and Chronicle’s art staff and freelanced on the side. Wilder worked as a commercial illustrator. The year 1985 was a great freelancing time for Cowles, too. The Village Voice published one of his caricatures as did American Illustration, an annual hardcover showcasing topnotch artists and image-makers.  

The couple had two children. Clayton was born in 1987 and Alison in 1992. Though Cowles and Wilder split amicably in 1995, they remained friends. Wilder later discovered the printmaking medium and is a certified Roycroft Renaissance Master Artisan. 

“Since our kids grew up seeing each parent earning a living as an independent artist, they didn’t suffer the usual discouraging advice about art careers,” said Wilder. Clayton and Alison are the family’s next generation of professional artists. 

Less is more

Cowles worked for the D&C on and off from 1983 until 1990. Nazareth College art professor Ron Netsky freelanced as a D&C art critic in the mid-80s. He was immediately drawn to Cowles’ work. 

“His illustrations and caricatures were unlike any I’d seen. While most illustrators were distorting faces – a kind of fun-house mirror effect – David was abstracting them. He was using wild colors and simple shapes, like Miro or Picasso, but still managing to nail the person he was illustrating,” said Netsky. “It was the freshest, most brilliant illustration I’d ever seen.” 

By 1990 Cowles’ client base was solid enough to freelance exclusively. Cowles had a weekly caricature assignment for Entertainment Weekly and other high profile clients like Rolling Stone magazine. 

Cowles’ early D&C caricatures were simplistic due to tight deadlines and the limitations of newspaper printing then. Over time, his minimalist style evolved, following a geometric direction inspired by Covarrubias with a dash of Picasso. Cowles added vibrant colors and began eliminating unnecessary features, like a second eye, if a portrait still retained a strong resemblance to his subject without them.  

“I remember a David Letterman with no eyes but he still somehow looked just like David Letterman,” said Netsky.

Cowles used colored pencils, then Gouache paint, for his caricatures but switched over to a digital format around 2005. It was a learning curve but the medium also lent itself to exploring using his illustrations in animation projects. His daughter Alison, a graphic designer, musician and writer, is his frequent creative partner. One such collaboration of many is Boots, a cartoon short for Frederator Studios. Boots first aired in November 2017 as part of the studios’ Go! Cartoons series. 

“I like collaborations in general, but she and I have the same sense of humor and the same taste in general,” Cowles said. “But when we brainstorm we can come up with fresh ideas that we might not on our own, and have enough differences to challenge the other when discussing ideas.”


Nannette Nocon and Karl Wessendorf of Rochester are major arts and culture supporters and big fans of Cowles. In 2012, they bid and won a portrait commission during a benefit auction for The Strong National Museum of Play (The Strong). They decided to have the portrait done for conductor Arild Remmereit – Rochester Philharmonic Orchestra’s musical director at that time. 

“Karl worked with Dave on the details and the maestro’s portrait was perfect!” said Nocon.

She and Wessendorf have since commissioned over a dozen portraits as surprise gifts for some local arts, nonprofits and business leaders who have inspired them plus more for friends and family.

“I love art that makes me happy when I look at it. Pure joy!” said Nocon. “So why not share David’s work with others?  I had seen his work in magazines and other publications. When I learned that he lives in Rochester, my desire to recognize his work became even stronger.”   

In August 2022, Nocon and Wessendorf commissioned a Cowles portrait of the two of them together as their 30th wedding anniversary gift to each other.

Looking ahead

As part of The Strong’s new museum expansion in June 2023 Cowles created portraits of three iconic video game characters. These will be reproduced as 7-foot-tall prints, set in massive custom-built frames and hung in the orientation gallery of the new ESL Federal Credit Union Digital Worlds exhibit (dedicated to the history and cultural impact of video games). Cowles has worked with the museum before. He illustrated three cubist-style portraits of other video game characters for a poster series. The series was awarded a 2022 Graphis Bronze award from the Graphis Institute, a career highlight for Cowles. 

Cowles has been regularly teaching as an adjunct art and design professor at Nazareth College since 2011. Presently, he teaches digital illustration and advanced illustration and currently has a retrospective show of his poster art in the Colacino Gallery at Nazareth titled “The Big Picture” (on display Feb. 10-March 5). 

The Rochester Contemporary Art Center is planning a Cowles exhibit. On a personal note, Cowles is engaged to Leann Macomber, his former neighbor. No official date has been set for either but embracing the unpredictability of the future is one valuable lesson learned from a mercurial freelancing career. Cowles rolls with it. He knows there will be good things on the horizon.

Creating a Caricature

When Cowles takes on a new caricature assignment, his first step is an internet search for photos of his subject. He views various angles and different expressions to establish the essence of the person. Cowles’ goal is to create a fresh and unique interpretation. He then prints a few photos to reference when he starts sketching. 

Cowles draws freehand with a pencil on tracing paper starting with the nose and working outward. 

“Sometimes I’ll get a likeness on the first try,” he said. “Other times I’ll try several variations to see what works best. Sometimes all the sketches look like garbage until one hits.” 

Occasionally he’ll take a break and when he looks at his sketches later, one will stand out as the obvious choice.

When Cowles is satisfied with the drawing, he scans the selected image into the Adobe Illustrator vector art app. Cowles digitally traces out the shapes over the sketch and then adds color to them. He exports that image and opens it in the Adobe Photoshop software program to add shading and texture. 

Once completed, Cowles exports the image in a JPG format. The file is ready to be sent to his client as an email attachment.

Learn more at davidcowles.net. Follow Cowles on Facebook, on Instagram @dvdcowles and TikTok @davyhobie.  

Leave a Reply

Your email address will not be published. Required fields are marked *