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John Dempsey: A Memoir
Judith Amtmann, Stratford-Way


In the northwest corner of John Dempsey’s studio are his drawing board and a high stool. There is a completed sketch on the board’s slanted surface. To the right is a shelf containing bottles of Dr. Ph. Martin’s transparent water colors and the white china dinner plates Dempsey used for palettes. To the left, nail hung, is an old white sock used for cleaning brushes, and a collection of soft-leaded  pencils. 

From this office/nest, nameplate on the door reading “Car 2 nst,” Dempsey created the drawings that made him world famous. This is the last of four spaces he occupied upstairs in the Stratford Square building over a period of 32 years. John Dempsey died May 18, 2002.

Memorable Nymphets

Chances are, if you have scanned a copy of Playboy Magazine any time between the late 50s and the present, Dempsey’s work is familiar. He had a full-page color cartoon in almost every one, and sometimes another in black and white as well.  Though content varied widely, most memorable were his buxom nymphets, all innocence, with attendant oglers looking anything but. The fine comic detail of both male and female facial expressions almost didn’t need the sly, dry wit of his captions, but together they gave his cartoons double punch. His protagonist was typically an “everyman,” caught with his pants down, thinking fast.

Typically, a batch of rough pencil sketches would be sent to Playboy, though “rough” never applied to Dempsey’s. His were complete right down to the type of flowers in a background vase.  Playboy would irregularly schedule conferences for cartoon selection, choose one or more of a batch for publication and return the sketches. Dempsey would then execute those selected in full color at his leisure. Other than for publication at Christmas (with choices made the previous July), there was no deadline. Cartoons could run months or even years after the completed work had been sent in and paid for.

The Imagined Playboy Life

Dempsey’s wife, Ann, says that when they were out together, people would gravitate toward John, craving a glimpse of the imagined life of a Playboy insider, eager to hear of Playboy Mansion parties and what it was like to be involved with one of  the most influential magazines in America. The very private man his family and friends speak of, however, never attended a Playboy party and met Hugh Hefner perhaps only once, and that after many years of association with the magazine.

Dempsey was born in 1919, the eldest of five children. Both parents were Irish, his father an evangelical minister. During his childhood, the family lived in Monrovia and his youth included work in the surrounding orange groves picking fruit and stoking smudge pots, raising homing pigeons, and drawing, always drawing. His high school notebook pages were filled to the margins with studies of horses and cowboys. After high school, still enamored with horses, he traveled a minor rodeo circuit, worked on a ranch in Arizona breaking horses and running cattle, but never owned a horse of his own. Sketches from this period, without formal training, display an already well-developed artistic ability.

Painter 2nd Class

Next was working for the Army Corps of Engineers, where he was signed on as a “surveyman” and sent to Costa Rica to work on the Pan American Highway. Bouts of malaria there resulted in rounds of quinine treatment, and eventual transfer to Alaska.  In 1943, he enlisted in the Sea Bees (construction arm of the Navy, consisting primarily of loggers, dam builders, structural-steel workers, etc. who built runways, pontoon bridges and primitive shelters for the troops that would follow them in). His official title was Painter 2nd Class, his job description: artist, cartoonist and (eventual) art editor of Sea Bee Magazine. They sent him to Hawaii, where he learned to play golf and remained until finishing military service in 1945. His daughter Joanna says he was always a bit ashamed to admit that during the war he had a great time.

Back home in California, Dempsey debated becoming either a civil engineer or an artist, opting to use the GI Bill to enroll at Chouinard Art Institute in Los Angeles.  While there, he became acquainted with two other artists who would later settle locally:  Del Mar sculptor Bob Mason and Encinitas multi-media artist Robert Perine.

Chouinard On the GI Bill

Perine remembers Chouinard in the late 40s as a place of driven students. The core curriculum was the same for all: drawing, design and painting - fine arts intended for illustrators and graphic artists. Many of the approximately 1000 students were former GI’s, matured by war and grateful for the opportunity of higher education not available without financial backing from the government. Dempsey attended for almost two years but did not graduate. Instead, with acceptance of a cartoon submission to Collier’s and $60 payment in hand, he dropped out.

Within a few years, his work was appearing in The Saturday Evening Post, Look, and Cosmopolitan as well as Collier’s, and his name became well known. He moved to Laguna Beach in the early 60s, joining an established and elite group of other cartoonists which included Phil and Frank Interlandi, Virgil Partch, Leroy Nieman, Ed Nofziger, Don Tobin, and Dick Shaw. Perine says that Dempsey’s work originally was family oriented, “featuring gags about kids, teens and husband/wife struggles.”  He remembers that about six months after the first Playboy came out, Dempsey submitted a “mildly ribald cartoon” accepted immediately, the beginning of close to 50 years of collaboration.

The Beauty of Del Mar

John and Ann Dempsey met and married in Laguna Beach.  Having often driven through and remarked at the beauty of Del Mar, they decided to move here in 1970. Children Jason and Joanna were born at Scripps in 1970 and 1972. Jason, now 32, is in Paris completing a Ph.D. at the Sorbonne and teaching English to prospective diplomats at Ecole Normale Supérieure. He will return to Del Mar in late July. Joanna, an art student, was away when her father became ill but came home immediately and was able to spend considerable time with him before he died.

Reflecting on her childhood, Joanna remembers her father “mostly as just a dad, very sweet.”

Family Drawings Preserved

Every birthday was commemorated by Dempsey’s drawings in the form of cards; “they'd be about the family, current pets and/or something we were involved in at the time,” she says, “and when we were apart for vacations, he used to make up stories using pictures for words and send them instead of letters, short but fun.” All are carefully preserved. Though quiet and introspective with others, Joanna says his interaction with her and her brother was lighthearted, his attempts to make them laugh a constant of her early youth.

As Joanna grew older and her interest and exploration of various art fields intensified, her father followed her classes and work closely, and began for the first time to speak of his own career and current projects, several of which are cartoon books of unpublished drawings he hoped she would be able to market through her connections when completed. He intended them as a legacy for his children.

“Quiet” and “gentle” are the two most common words used to describe Dempsey by friends, personality traits that perhaps carried over into not showing collections of his work. Perine several times proposed this, once taking photographs of over a hundred of John’s drawings with this in mind. “He had a way of refusing to do things. He was very articulate visually -  notice the lamps, chairs and accouterments in his work, all very complete -  but not verbally. He was self-effacing, quiet and slow of speech, not assertive at all. He wouldn’t say no, he’d just pause and you’d wait for the end of the sentence. But then his eyes would wander and you’d realize he wasn't going to say any more.  We never did the exhibition.”

Along with Perine and Solana Beach artist and friend Steve Beck, Dempsey belonged to a loose-knit group of artists that met locally once a week for many years. Beck describes his friend as “the most genuine artist I ever met. He had a wonderfully human way of looking at the world, full of irony, entirely unaffected.”

“I’m Using You”

Conversations and situations brought up at these weekly gatherings often provided Dempsey with material, later to appear in Playboy, names changed.  “‘I’m using you,’ he’d say, ‘first name only of course.’ And we'd recognize ourselves,” says Perine.  “He’d describe his drawing, sometimes hand it to us, laughing.” 

“Ideas are the most important part (of being a cartoonist).  You might be able to draw and draw well, but if you don’t have an idea, you won't get anywhere.” (John Dempsey, quoted from The Surfcomber, June 23, 1983, wherein it's also mentioned that he often found his inspirations for contemporary lifestyles in dress and conversation right here in Del Mar.)

Still a Mentor

On a desk in his office, Dempsey kept a folder of fan mail and requests for his autograph, most of them also pleading for a small sketch. The letters are current, indicating he was still an influential and encouraging mentor. Also current were his cartoon contributions to life in Del Mar. Sandpiper has been privileged to publish a number of them over the past several years, the most recent being in our May issue this year.

Though his lifestyle was modest in the extreme, he was very appreciative of the life he was able to create. Self-promotion and greater success were not a goal.  He loved what he did.  He once told his daughter Joanna, “I’ve always felt I had the job every man would want, making people laugh for a living.”


A memorial service for John Dempsey will be held Tuesday, July 30 at 5:00 pm, in Seagrove Park.


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