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Richard H. Wiley

The Story of Portland’s Most Prolific and Pioneering Illustrator

By Melissa Delzio

Wiley's billboard illustration for Olympia beer, 1956

Portrait of Richard Wiley at Studio 1030 around 1960

Richard Wiley described art and illustration as both his purpose in life and his tormentor; his paycheck and one of the “…greatest ways in the world to make a fool of yourself.”

Over a prosperous six-decades-long career as an independent artist in Portland, Richard’s fashion illustrations helped build up Portland’s reputation as an industry leader in apparel. His humor and camaraderie with fellow independent designers at Studio 1030, in combination with his community-minded perspective, helped build foundational design organizations in this city. Richard garnered national attention as a portrait artist, yet persistent bouts of self-doubt kept his ego in check. But before he laid down the first paint strokes in the Pacific Northwest, he was a young boy with dreams of being a cartoonist in Virginia.

Art as an Escape from Academic Drudgery

Richard Henderson Wiley (known as Dick to his friends) was born July 26, 1919, in Lynchburg, Virginia. His father, Edgar Clarence Wiley, was a prolific mechanical engineer and inventor. By age 18, Edgar already held four patents. Young Richard often felt he was in the shadow of his father’s genius, but he was determined to carve out his own path. Positive reinforcement of Richard’s talents were established early, particularly by his mother who, at age seven, proclaimed him to be a “gifted artist.” This was all the encouragement the young boy needed to launch his artistic dreams.

He started making art for anyone interested (including early portraits of his grandparents) and expressed an interest in cartooning. Notoriety for his work spread by junior high. Richard’s daughter Denise Wiley says, “He was always the guy in school they would go to when they needed a drawing of something.”

“Talented, accommodating, forgetful and obstreperous,” was the 1934 description highlighting a young Richard Wiley in the E.C. Glass High School news weekly, unironically named High Times. The High Times was a publication that balanced out its use of the 5-star vocabulary word “obstreperous” (meaning unruly or boisterous) with the colloquial use of words like, “‘tis” and “‘rithmetic” to convey a down-to-earth sensibility. Regardless, the high school publication wrote a full article about the talented young artist who wasn’t even in high school at the time.

As a junior high school student, Richard was allowed to take Margaret Helbig’s art classes at the high school. Ms. Helbig was an artist in her own right known for landscapes, figure painting and floral studies. About Richard, she expounded, “For he showed such remarkable talent, I suggested that he come to Senior High for extra periods. He takes art ten periods a week and is completely wrapped up in his artwork.” However generous Margaret was, she may also have been the same art teacher whose judgement he battled later in life. The teacher’s proclamation that, “Real artists never use photographs,” stayed with him, and his reliance on photography made him feel like a lesser artist, thus undermining his confidence.

Richard’s early interest in art in school may have served a dual purpose. In a 1971 article, Richard himself admits art was an escape from academic drudgery. He said, “I found out as a boy that I could get out of dirty details like spelling when I could draw pictures.”

In addition to taking advanced art classes, Richard’s prolific talent earned him the position of Art Editor of High Times. A high honor indeed. For the publication he provided cartoons, which were full of insider references to students, teachers and principals. In Richard’s early work, we see almost no examples of personified animal characters; rather we see sophisticated renderings of figures that are anything but childish. Inspiration came right from the comic section of the newspaper, especially the Price Valiant strip by Hal Foster with its more detailed and realistic epic panels. Richard’s characters are drawn in a style that is more reminiscent of 1930s Dick Tracy comic strips than the “rubber hose” cartoon style which was en vogue (for example, the noodle-y limbs of characters such as Felix the Cat). His panels were signed with a signature that resembles the famous signature of Walt Disney. According to his son Ryan Wiley, as a young man Richard, “took a correspondence course in cartooning, where he would get an assignment, draw the character, send it in and receive ‘professional feedback’ and suggestions in return.” This practice and process would be the foundation for his future career in illustration.

Once in high school, Richard was awarded the task of illustrating covers for The Critic, the high school’s literary magazine, as well as programs for musical performances and other design ephemera. A few of Richard’s The Critic covers show bolder experimentation, dramatic lines and the drama of positive/negative spaces.

Richard’s lackadaisical attitude toward his traditional studies and overall class clown status was highlighted in the High Times article, but it seems as though young Richard’s charm and talent won over his teachers to a degree that they made accommodations that steered him on a career path that he stayed on throughout his whole life. In these early days, Richard established behaviors that would serve him throughout a long and illustrious career: an eagerness to please others and a proclivity toward perfectionism that would prompt him to draw the same subject or scene over and over again until he was satisfied. When asked what he wanted to be when he grew up, he would proudly declare that he wanted to be a cartoonist.

Lucky for us, he was encouraged by his parents and teachers to follow his ambition and set his sights on attending Syracuse University in New York to study Fine Art.

Richard was as adventurous as he was talented—before starting college, he and a friend took a boat across the Atlantic for a summer of cycling and sketching across Europe. They started together in England, but his friend soon encountered a lady friend. Undeterred, Richard set out on a solo bicycling tour of France. Given his youthful charm and boyish good looks, this cycling American artist was not alone for long. His family recounts that he also made a few lady friends of his own on this journey.

"Syracusan" Magazine cover design

When he finally landed at Syracuse in 1938, Richard set about the task of proving himself in a new territory. Soon he was providing cartoons and illustrations for the college’s student newspaper, The Daily Orange (the official school color). His cartoon subjects ranged from the college-sports themed to the political as propaganda rhetoric heated up in a nation torn about the emerging war in Europe.

In college he began getting paid for his illustration work, freelancing for a very conservative anti-tax newspaper in New York, aptly named New York State Taxpayer. He would submit two or three drawings to the publication’s specifications and he was paid $5 for whatever they chose. He would have a really good month if he earned $20! That would be worthy of writing home to his mother, who would caution him to save some of that money. In some comic panels for the Taxpayer, the sports metaphors and political metaphors combine as in this entry from 1940.

Richard’s work also reflected his hobbies and interests. In Syracuse he picked up skiing for sport and leisure, putting together an informational zine promoting university trips and illustrating a ski-themed cover of The Syracusan, the college’s magazine.

Richard was also a member of an all-male Syracuse cheerleading squad. This may seem surprising given the current demographics of the sport, but the 30s was an era when a majority of colleges were all-male and cheerleading, still a newer sport in the U.S., was dominated by men. In fact, according to an Atlantic article on the subject, “Cheerleading was still seen by some as ‘too masculine’ for women.” One author goes so far as to say that he feared cheerleading would promote the development of women’s “loud, raucous voices.” Syracuse however, bucked the trend on this and had a men’s and women’s squad. Richard, ever the standout, was the only man on the men’s squad to be able to achieve the very difficult forward flip.

Richard’s booming college career would come to a screeching halt, however, after he finished his junior year. He was drafted into the army in the summer of 1941. Richard never returned to complete his degree.

No Shooting, Just Art

The Army Years (1941-1946)

1946 portrait in Army barracks

While reluctant to give up college, Richard knew that following his brothers into the army was inevitable in this time of national turmoil. Yet little did he know, his military service would be rather ideal, by comparative standards, and would help him launch his career in design. In fact, it was his talent as an artist and his ambitious nature which prevented him from being sent to the warzone.

Richard was initially stationed at Fort Belvoir in Virginia and later, Texas. One Texas summer day, a day off when all of the other guys went swimming, Richard had a different plan. Ryan recalls the story he heard as a child, “He went to go talk to his commander, to tell him that he was really interested in illustration, and to ask if there was some way he could do that. The commander said yes, as a matter of fact, there was an opening in Portland, Oregon for a map designer.” Richard expressed eagerness at the idea and signed the transfer right there. He then relayed that it was a good thing he had come in when he did, because all the other guys were being shipped out for combat duty the next day. “It changed his life and made all of us possible. If he had gone swimming that day, we wouldn’t have been born,” Ryan says, referring to him and his two sisters.

Richard joined the 29th Topographic Engineer Battalion, one of two active topographic battalions, and the oldest of all U.S. military mapping units.

During war years, the 29th was working on mapping the U.S., particularly the Pacific coastline. They experimented with using aerial photography, replacing guns with cameras on planes for the creation of maps. The Battalion had been stationed in Portland since 1937, transforming the old Glenhaven school in SE Portland (now Glenhaven Park) into a base, complete with army barracks. Conveniently, Richard was stationed right next to the Rose City Golf Course, which in a later interview he laughingly credits to his stellar golf skills.

Jack Dumas (left) and Richard in front of Oregon Journal billboard he designed! (1943-1945)

Oregon Journal entry 1942 on soldier's exhibit

Richard started making his mark in Portland immediately upon arrival. A 1942 Oregon Journal article showcases Richard’s watercolor “Frustrated Fighter” as part of the 22-man Soldiers Show held at the Portland Art Museum. The exhibit also featured fellow soldier Jack Dumas, who was known for his lively caricatures and who became a fast friend of Richard’s. Richard’s portrait of a soldier was likely not reflective of his own state of mind at the time, as he was enjoying exploring his new city and his illustration career was about to take off.

Many Army mapmakers were also talented illustrators and they were young and hungry for more work. So, after hours Richard and Jack would head to downtown Portland and “scrounge work” from various advertising agencies. There was much demand because so many young illustrators had been drafted. Richard and one Army friend felt they had enough freelance work to warrant renting space in an attic to set up their own commercial art studio. This was Richard’s first peek into what the career of a commercial artist was like.

Racist depictions were common in this era of propaganda.

During his time in the service, Richard also was stationed in San Francisco, working at The Presidio. As he had since junior high, he continued to produce cartoons, contributing drawings to many Army publications. He submitted his inside perspective of Army life to bigger publications, even national magazines like Collier’s and Esquire. The Army took notice of his talent and Richard started making posters with security-related messaging. A major theme of American WWII propaganda posters was to encourage soldiers to keep quiet and to make sure they did not inadvertently give away military secrets while bragging or gossiping.

Jack Dumas (left) and Richard out on the town with dates in San Francisco

1942 Don't Be a Blaboteur Poster

In a 2009 OPB interview, Richard reflects, “I was in San Francisco and I had a little drawing board and place to work, and a printing press right beside me, and I’d make these posters. I made posters that said things like 'Don't be a Blaboteur,' which is a word that I am proud to say that I invented. I used it until people couldn't stand it anymore.’”

His “Blaboteur” series, encouraging servicemen not to blab, started gaining national attention. A March 12, 1942 edition of The New York Post features one black and white version of the poster and touts Richard’s second place finish in a contest and his reward—a wristwatch. But having his work published in full color in popular national magazine Collier's, was the feather in the cap for the young illustrator. Collier’s had announced a challenge to illustrators across the U.S. that they called the “Shut-Mouth Poster Awards.” Because, “Collier’s believes, as you do, that rumors should be suppressed, that loose talk is dangerous.” The text goes on to use a racial slur against the Japanese that was common at the time.

Racist depictions were common in this era of propaganda.

Collier’s May 30, 1942 issue featured the poster contest winners and among them was Richard Wiley. His Blaboteur poster submission features his witty copy, as well as a blabbing gentleman carelessly giving away military secrets. In addition to having his poster featured in Collier’s in color, Richard received a cool $100 in prize money. In a few short years, he had come a long way from his college freelancing gigs.

Some of the other posters chosen lean heavily into sinister depictions of Japanese people. Richard illustrated a few posters of this nature too, including the New York Post submission. Othering language and racist depictions were typical of WWII wartime propaganda posters internationally, but they are startling to view today, knowing how this propaganda affected Japanese-American citizens during the war period.

Racist depictions were common in this era of propaganda.

During the war, Richard was never sent overseas for combat. He was content to do battle with pen and paper. Denise summarizes her dad’s war years succinctly as, “No shooting, just drawing!”

Portrait of Maj.Gen. C.H. Bonesteel, Presidio, 1944

In 1945, when the fighting was over, Richard and the 29th Topographic Engineer Battalion was sent to the Philippines to begin a “Post- Hostilities Mapping Project.” A booklet about the project authored by soldiers and illustrated by several of the artists, including Richard, goes into snarky detail about the conditions of the ship they sailed on, reporting that “We found there’s nothing quite as refreshing as to walk up to the yawning mouth of a booby hatch and be knocked off your feet by a blast of hot air, redolent with the fragrant, tantalizing odor of beans. Beans for breakfast! Bean soup for lunch, too. Though sometimes, to our disappointment, we were unable to have them for dinner.”

Upon arrival in the Philippines, Richard and the young soldiers saw the after effects of a war zone for the first time. The locals called them “Victory Joes” and tried to sell them loose cigarettes. The booklet states, “In Manila, we saw our first close up of what a 155 does to a brick wall. The Walled City lasted for some three hundred years, but now it looks as if it had been gone over with a big potato masher.”

Scans from 1945 "So We Went Overseas". Richard marked his illustrations and paintings with a red check.

The soldiers moved about via their own fleet, revelling at the site of sunken Japanese ships in the water below. They travelled with cameras and sketchbooks, taking in the scenes. Richard’s captions with his drawings (copies of which he sent home) describe locals gathering around him to watch him draw. He enjoyed the attention. One caption cites, “Ants nearly ate me alive before I finished this one.” The booklet of their experience, complete with many of these photos and drawings, was bound as a memento for the men who served and is called, “So We Went Overseas.”

Richard, now 27 with his Army years behind him, was free to move forward with his career ambition, to become a commercial illustrator.

The Wolf of SW Washington St.

In January of 1946, Richard set his sight on the epicenter of the design world: New York City. He made appointments, met with people and found out very quickly that the reality of working as a commercial artist in the big city meant that it would be many years before he could make a living. It was—and still is—very competitive and expensive to live in New York City.

Meanwhile, his Army buddy Jack Dumas, whom he had worked with in Portland, started wooing him. “Come back to Portland!” he said. “You can start working with us here right away.” Richard had loved Portland, with the mountains and the beaches close by, so it wasn’t a hard decision to make.

As Jack promised, Richard’s career took off when he arrived back in Portland and started work at the Associated Designers studio. Associated Designers was opened in 1946 by illustrator Pers Crowell, and was first described plainly as, “Six Portland artists work independently for Pacific Northwest Industries”. Associated Designers is the studio that later became Studio 1030, when they grew in size and moved to 1030 W. Burnside. In these early years, the studio was located in the New Fliedner Building at SW 10th and Washington. The concept was the same; a collective of creatives with different skill sets who rented a desk from the studio head. The designers collaborated and shared work often. A secretary would manage incoming requests, run errands and often model for illustration work.

Members of Associated Designers, left to right: Roy Brear, Ray Rogers, unidentified, and Don Kopp

On the day Richard was set to arrive for his first day of work, Lois Wilma Wilson was the secretary at Associated Designers. A Portland-born Grant High School graduate who had her own artistic ambitions, Lois heard from Jack Dumas about the new illustrator arriving. Her daughter, Denise explains, “She heard they were getting this new guy. They called him ‘The Wolf’. He was preceded by a reputation as a real ladies man. She thought he would have a long chain watch swinging around and a zoot suit. She met him at the elevator as everybody came to meet him and she thought, ‘Wolf?!? This is no wolf!’” Richard had arrived with saddle shoes and clothes that didn’t quite fit right because he was fresh out of the army. The other woman in the studio had said to Lois, “Stay away, he’s mine!” And Lois told her, “No problem!” Lois had her own plan in the works. She was set to depart from Portland with a friend to try to make it in Los Angeles. Their plan was to lounge at the beach by day and work theater jobs by night. Unfortunately, their plans fell through when they found L.A. to be too competitive. When their money ran out, they boarded a train back to Portland.

Ad featuring Lois Wilson (Jack-Dumas illustration)

Luckily, Lois found Richard right where she had left him. Apparently, the other woman in the office had no luck with “The Wolf” and Richard, smitten with Lois from the start, was brave enough to ask her on a coffee date. Thus their two-year courtship began, resulting in their marriage in 1948. The newlyweds rented an apartment downtown on SW Jefferson. Their first apartment, like all their subsequent homes, was thoughtfully designed and curated, as they both had a knack for interior design.

In addition to finding love, Richard was figuring out how to build his career. Even in the 1940s, apparel was king in Portland, and in order to make a living, Richard learned he would need to embrace fashion illustration—or as he later called it, “figure illustration”. This was illustration’s heyday, before photography became the default in fashion advertising. His first freelance job as a member of Associated Designers was for Lipman Wolfe, Portland’s grandest department store. Richard later recalled, “One day, the Lipman Wolfe department store in Portland had a job they wanted for men's hats. I'd never done an assignment like that before.”

The members of Associated Designers had a lot of fun at work, as evidenced by several entries in a gossip/culture column that ran regularly in The Oregonian titled, “Behind the Mike.” A 1949 entry describes a particularly potent office prank: Richard had been drawing a picture of smelt, using a real, dead fish as a model, and according to the report, when he finished, “ …He thought it would be a shame to throw such a useful fish away.” So, he scotch-taped it to the underside of colleague Pers Crowell’s chair. Pers apparently didn’t hunt for the source of the odor; rather he opened a window, resisted being at his desk and complained of feeling ill.

Eventually Pers was made aware of the prank and weeks later, the Oregonian followed up with a report that he got Richard back by placing an ad saying that Richard (Dick) was an expectant father in dire need of a baby carriage. The Oregonian reports, “Fighting a deadline on a rush art job, Dick has had to spend the better part of two days on the phone explaining to irate women that he’s really the victim of a revenge plot dating back to a dead fish. At any rate, Dick has made up his mind on one thing. ‘If I ever do need a baby carriage,’ he says, ‘I’ll be sure to advertise. It certainly gets results.’”

Dick and Lois's First Christmas

Indeed, Richard and Lois were soon in need of a baby carriage with the birth of Denise in 1951, then later Ryan in 1954 and Lyn in 1957. Right before Lyn was born, the couple decided to build their dream home on a beautiful lakefront property in Lake Oswego. At a $34,000 price tag, they built a mid-century modern house on the lake that Richard and Lois both helped design. Ryan says, “Dad said he made two great decisions in his life: marrying our mother and building that house.”

Richard would commute daily by bus to Associated Designers in downtown Portland. Richard’s children remember their father’s days working downtown, saying they used to rush to meet him at the bus in hopes he would buy them candy, which he often did. Sometimes, Richard’s own artwork would adorn the bus. Daughter Lyn Blessing remembers she would be, “…riding the bus downtown and his ads would be on the rack on the top of the bus. I was so proud that my dad’s ad was there, I could recognize his art on those old blue busses.”

People Sell People

Wiley's billboard illustration for Olympia beer, 1956

Unknown Artist, but from same series

Richard’s work found an even bigger canvas in a series of billboards for Washington-based Olympia Beer. Richard’s 1956 billboard series exemplifies the evolved sophistication of Richard’s illustration style. The Olympia Tumwater Foundation has an archive of this work and they report, “The original paintings offer a unique glimpse into the art and advertising processes of the day. Completed long before computer technology …most of the pieces were produced by artists (like Richard) hired by the Seattle advertising agency of Botsford, Constantine & Gardner.” The archive goes on to give insight into the process of billboard-making, “In the 1930s and early 1940s, a billboard painter used each small painting as a guide and hand-painted the large-scale version onto a billboard. Later, when printing processes improved, the original paintings were enlarged and printed onto heavy paper—installing billboards then became a much simpler matter of pasting sections of paper, much like wallpaper, onto the wooden billboard backing. Up to 24 or 30 sheets of paper constituted a billboard.”

While the Olympia billboard project was a career high point, fashion illustration was Richard’s bread and butter. Richard had slowly gained the trust of big name apparel clients based in Portland like White Stag, Pendleton, and Jantzen. A 1954 article in the Oregonian’s Northwest Magazine named Portland as a top apparel center; the “world’s largest producers of ski-wear and swim­­ sits, umbrellas, sportswear, leather garments, sweaters…and straight work clothing.” The article highlights the elegant side of the industry, with beautiful models in high demand, as well as “fashion artists” like Dick Wiley, shown with his sketchpad drawing a female model in White Stag clothing.

The reality was not quite as glamorous as the magazine describes. For one, Richard rarely drew from real life, instead preferring to use his camera to shoot his models in the clothes in a variety of poses. His son Ryan describes, “He would use anyone he could to model, very rarely professional models. Lots of family, friends, neighbors, our school chums.” Denise remembers one particular living room scene, “I was just thinking of Jack and Tom (the neighbors) in the living room trying on White Stag clothes, with me running back and forth peeking,” she laughs as she recalls her spying attempts. To get the proper look, Richard was resourceful, even going to furniture and department stores asking to borrow furniture as props for his work.

His children became models when he was tasked with illustrating the Jantzen swimsuit line for kids. Ryan jokes, “Yes, I am a swimsuit model.” Richard would get Ryan a little stool so he could pose on it like it was the pool ladder. “He would ask me to pretend like I was coming out of the pool. He would take picture after picture, saying, ‘OK curl your hand this way. OK, hold it right there.’” Richard would art direct his models until he got the scene just right.Once he had the shot, he would take the film and he would develop it in the bathroom. Ryan explains the process from there, “He would have strips of film hanging everywhere until they dried. He would cut them up and have them printed … in downtown Portland. He would come back with the printed pictures. He marked the ones he liked, put crop marks on it and would start with sketches. I don’t know if he submitted the rough sketches, but at some point he would share initial work with the client. And they would say, ‘Oh good, but double check this pocket, this pocket looks way too big on the item.’ So he would go back and do that, and eventually churn that out. And that would be the ad.” Richard primarily used gouache for the final commercial artwork, never airbrush. He did not set type or do custom lettering, but sometimes would draw the letters from a logo.

There were some things Richard was called to illustrate that he could not take custom photographs for. For that, he kept a huge file cabinet of reference photographs. Ryan reminisces, “He was forever tearing things out of magazines, leaving piles of them and then hiring us for 25 cents an hour to file them for him.” He would have hundreds of photos on each topic—look up “h” in the filing cabinet and there would be piles of horse photos. Ryan describes his father scouring every magazine he could get a hold of. These reference libraries were a necessity for illustrators in the days before a Google image search could return thousands of results on command.

Being connected to the other designers at Associated Designers made it easy for Richard to stay connected to the small but collaborative creative community. He was a charter member of the Portland Art Director’s Club, which started sometime in the 1950s. According to fellow member, Tom Lincoln, the club was formed to “talk shop.” He says they exchanged advice about client relations, establishing business norms around billing and worked to try to elevate the perception of commercial art in the community. Like design organizations today, the Portland Art Director’s Club had an awards show and in 1957 Richard won an award for a Seattle Transit ad he designed for Cole & Weber, a popular ad agency.

By 1960, Associated Designers had become Studio 1030 and moved to their W. Burnside home (in what was most recently the Fez Ballroom). The studio had sales sheets made up to promote each independent artist. Richard’s states, “With his wife and three children, he likes to get away from the world of art and into the world of physical activity…golf, swimming and boating. Other than being an ex-Virginian, he will confess to no other interesting personality traits. We are proud to have him on this area’s advertising team.” Even in his sales sheet, Richard was humble and self-deprecating in his sense of humor.

Another Studio 1030 sales sheet from the early 1960s states: “Action drawings of people—in color and in black and white— are the specialty of Dick Wiley of Studio 1030. …People sell people. When real people—consumers, that is—see Dick’s people enjoying the taste of a certain beer or looking well-dressed in a certain brand of clothes, the real people are motivated to do likewise.”

Richard Wiley’s illustrated ads set mid-century trends for a privileged, white audience and he was about to get a national gig that would—for better or worse—define his career.

Meet Sally, Dick & Jane

In 1958 Richard received a letter from a New York artists’ representative inquiring about a project for a publisher who promised consistent work. The recruiter was reaching out to Richard on behalf of Scott, Foresman & Co, a book publisher out of Chicago that specialized in books for early readers.

1957 ad that attracted the publisher

The publisher had seen an illustration that Richard had made of a young middle class white family at play in their suburban home for the West Coast Lumberman’s Association. This illustration style was just what they were looking for as they sought to add a new illustrator to their roster for the very popular Dick and Jane reading series, which they were planning to update.

The Dick & Jane series was thirty years old by the time Richard lay the first paint stroke bringing to life the characters: older boy Dick, his sisters Jane and Sally, Puff the cat and Spot the dog. Very popular with the baby boomer generation, the books were “…first published in 1930 and used simple, repeated words alongside illustrations to teach young students to read,” according to an official source.

Richard, along with others, illustrated this book series until its demise in 1965. His association with the famous characters earned lots of press and attention and most importantly gave him a much needed stable income. When asked what Richard was trying to accomplish, when he drew, Sally, Dick and Jane. Richard honestly replied, “Make a little money!”. He went on to say, “They made you make money because of the deadlines. If you didn't get it done on time, you could forget it. The prices for the illustrations were established and they made you do it promptly, and that was good financially… for me.”