Comics and Cartooning in Westport From the Westport Public Art Collections

"Famous cartoonists are our neighbors, they are part of our heritage, the part that keeps us smiling." —Mel Casson, Westport CT

The Westport Public Art Collections contain over 120 original drawings for comics and cartoons by renowned masters of the art form. On display in school and town buildings, they continue to elicit smiles, chuckles, and recognition across generations of viewers.

Many cartoons in the WestPAC collection date to the mid-20th century, an era when American comics flourished. Comic books emerged as a stand-alone genre, beginning with "Superman" in 1938. Magazines like The New Yorker and The Saturday Evening Post published cartoons throughout their issues, while newspapers printed daily syndicated comic strips—many of which continue to appear today. And who didn't eagerly look forward to the full-color Sunday funny pages?

Bill Hoest, Agatha Crumb (1981), pen and ink on paper

A defining feature of comics is the creative interplay between pictures and words, giving them storytelling power. In some comics, writers and artists work together in a collaborative process, while other cartoonists create the entire work themselves. Most cartoons are done in pen and ink on paper. Roughs—and in some cases finished works—could be sketched in pencil or charcoal.

Syndicated Cartoons

Syndicates represent the artists and facilitate the publication of comic strips in daily and Sunday newspapers across the country. Cartoonists were known to work against tight deadlines, often hand-delivering the original artwork to the production departments of such syndicates as King Features and the Newspaper Enterprise Association.

(left) Frank Bolle, Encyclopedia Brown (1979) pen and ink on paper

Gag Cartoons

Gag cartoonists, who made single-panel cartoons with a caption, usually made weekly rounds to sell their work to such magazines as The New Yorker, The Saturday Evening Post, Esquire, Playboy, Argosy, Colliers, and True. They would take an early train into Manhattan for “look day,” usually a Wednesday, visiting the highest-paying publishers first!

Donald Reilly, Irish Hat (1976), carbon pencil and charcoal on paper

At these meetings, the cartoon editor would flip through the portfolio of penciled roughs, maybe selecting one or two of the artist’s ideas to consider publishing.

Westport, a Community of Cartoonists

In this era before fax machines, scanners and email, physical proximity to New York City was essential for work, as that's where the magazines, book publishers, and syndicates were based. Benefiting from being only 50 miles from the City, many famous cartoon artists lived and worked right here in Westport.

Working from an at-home or a rented studio, the artists all shared one thing—the solitary aspect of their work as they tried to develop new ideas. But they also enjoyed being part of the larger art community in town, taking needed breaks from the studio and becoming once-a-week lunch companions at local restaurants like Mario’s across from the railroad station, or mingling at Max’s, the downtown art supply store.

Mel Casson

Mel Casson (1920-2008)

The dean of the cartoon community in town was Mel Casson. He began his career in 1937 when he was the youngest cartoonist at age 17 to sign a contract with The Saturday Evening Post. His strip, “Mixed Singles,” later renamed “Boomer,” was nationally known.

Mel Casson, Boomer, pen and ink on paper (detail)

Casson knew everybody that was anybody in cartooning. He persuaded his colleagues to donate their original artwork to the Westport Public Art Collections in the 1960s and 70s and contributed extensively from his own private collection of cartoons. The strength of WestPAC's cartoon collection is in large part due to his efforts and generosity.

Gems in the WestPAC Cartoon Collection

Dean Young and Jim Raymond, Blondie (1979) pen and ink on paper


Originated in 1930, "Blondie" was the most successful comic strip in the world by the end of the second World War, and earned its originator, Chic Young (1901 - 1973), the huge yearly salary of $300,000. It remains popular today, appearing in more than 2,000 newspapers in 47 countries and translated into 35 languages.

After Chic's death, the strip passed to his son, Dean Young. Popular comic strips were often passed to new artists—rather than discontinued—when the originator retired or died. Dean continues to write the script, collaborating with artists including Westport-based Stan Drake, who drew the strip from 1984-1997.

Stanley Albert Drake and Dean Young, Blondie (1965), pen and ink on paper.

"Little Orphan Annie"

Over its long history, the syndicated strip “Little Orphan Annie” was written and drawn by not one but two Westport-based artists.

Harold Lincoln Gray, Annie (1967), pen and ink on paper

Harold Lincoln Gray (1894-1968), who moved to town in 1929, originated the strip in 1924 and drew it for over 40 years. WestPAC has one original “Annie” drawing by Gray (above), dating to his final years.

In 1979—after the success of the Broadway musical Annie—another Westport-based cartoonist, Leonard Starr (1925-2015), revived the Annie strip, and continued drawing it through 2000.

(background image) Leonard Starr, Annie (1984), pen and ink on paper

Original "Annie" comics and a selection of other cartoons were exhibited at Long Lots Elementary School for the student production of the musical Annie Jr.

A young actor in the role of Annie at Long Lots Elementary

"Mary Perkins, On Stage"

Leonard Starr, On Stage (1966), pen and ink on paper

Leonard Starr's comic strip "Mary Perkins, On Stage" followed the career and adventures of a Broadway actress. It ran from 1957 through 1979, and won numerous awards from the National Cartoonists Society. Starr moved to Westport in 1970, and worked alongside Stan Drake in a second-floor studio a few doors down from Max's Art Supply. Another renowned cartoonist, John Prentice ("Rip Kirby"), worked across the hall.

"The Heart of Juliet Jones"

Stan Drake, Juliet Jones (1975), pen and ink on paper

Stan Drake created "Juliet Jones" in 1953 and continued working on the strip through 1989. He moved to Westport in 1960 joining a thriving community of cartoonists and illustrators. Among his friends in town was Curt Swan (1920-1996), artist of the "Superman" comics for three decades.

Stan Drake (1921-1997)
Stan Drake, Caricature of Curt Swan, pencil and photograph on paper


Bud Sagendorf, Popeye, Olive and Wimpy (1956), pen and ink on paper

Bud Sagendorf (1915-1994) started his cartooning career as a teenage assistant to "Popeye" creator E.C. Segar. Sagendorf eventually took over the "Popeye" comic books and strips, and settled in Westport in the 1940's. Cartoon artists were often commissioned to draw humorous advertisements for local charity drives, such as the Red Cross or United Way.

"Amy" and "Henry"

Jack Tippit, Amy (1978), pen and ink on paper
Jack Tippit, Henry (1979), pen and ink on paper

Jack Tippit (1923-1994), known for drawing the syndicated comic strips, "Amy" and "Henry," also lived in Westport and served as the editorial cartoonist for the Westport News. He helped Mort Walker (1923-2018, creator of "Beetle Bailey") found the Museum of Cartoon Art in 1974. "Henry" was later drawn by another renowned local cartoon artist, Dick Hodgins (1931-2016).

"Side Glances"

Gill Fox, Side Glances (1978), pen and ink on paper

Gill Fox (1915-2004), is described as a "jack-of-all-trades" for his work across the many genres of cartooning, including syndicated strips, comic books, gag panels, advertising, illustration, animation, political cartooning, caricature and sports. His "Side Glances" was the longest-running single-panel newspaper cartoon, which he drew from 1962-1982. Fox drew political cartoons for the Fairfield Citizen, and lived nearby in Redding CT.

"Dear Fellow Globetrotter...."

Alice Harvey Ramsey, "Dear Fellow Globetrotter....", pencil and charcoal on paper

Alice Harvey Ramsey (1895-1983) was one of the first cartoonists for The New Yorker, starting her work for the magazine in 1925. She created three covers for The New Yorker, and was among a number of women making cartoons and illustrations for the publication during its early days. After living in New York and Bridgeport, she moved to Westport with her family in 1929.

Whitney Darrow Jr., Mother, carbon pencil, charcoal, and watercolor on paper
Illustration from Famous Artists Cartoon Course (1956)

Whitney Darrow Jr. (1909-1999) was a cartoonist for The New Yorker for almost 50 years, publishing more than 1500 cartoons in the magazine. A favorite subject for Darrow was suburban couples, familiar from his many years living in Wilton. Darrow also helped create the Famous Artists Cartoon Course.

Distance Learning 1950's-Style: The Famous Artists Cartoon Course

Two volumes of the Famous Artists Cartoon Course (1956)

For aspiring cartoonists, the Westport-based Famous Artists School began offering a correspondence course in 1956. Students received three large binders of lessons, created by luminaries of the art form such as Whitney Darrow Jr., Rube Goldberg, Al Capp and others. Completed assignments were mailed in to the school for feedback.

(Left and above) Pages from the Famous Artists Cartoon Course (1956)

A New Generation of Cartoonists in Westport

The proud tradition of creating comics and cartoons continues today among Westport Public School students, including in the formal art curriculum, in extracurricular clubs, and as individual pursuits.

(Right and above) Character studies by Grace Kennedy, SHS '20, WestPAC Senior Intern '20

At the middle-school level, the Bedford Comic Book Club meets weekly, and produces an annual comics magazine of student work.

"Our Bedford Students have used their comic creations as vehicles for self discovery to safely travel the uncharted waters of life in, as they find out more about themselves and the ever changing world around them." —Club director and BMS art teacher, Mark DeRosa
Pages from the 2018-2019 Bedford Comic Book

During the school COVID-19 shutdown, Mr. DeRosa taught a digital comic strip unit for his classes. Students created comic strips using found and digitally drawn images. Below are a few examples of student work:

Thank you for exploring with us!

Selected Bibliography and Resources

To learn more about the Westport Public Art Collections (WestPAC) and to Search the collections visit westportarts.org

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Created By
Westport Public Art Collections (WestPAC)


All photos are from Westport Public Art Collections, except: Grace Kennedy cartoons courtesy of the artist; BMS student work courtesy of Mark DeRosa; Annie photo courtesy of Dianna Betit; Stan Drake photo via Wikimedia Commons; Mel Casson photo King Features via https://westportnow.com/index.php?/v2/comments/20384/