A Curious Man

by Neal Thompson

  At Santa Rosa High, he got help toward that goal from an unlikely patron.

  FRANCES LOUISE “FANNY” O’MEARA, daughter of a feisty Oregon newspaperman, started teaching English in the late 1880s and would dedicate her entire life to Santa Rosa High. “Beloved” is how most graduates would describe her, as well as “tenacious” and “strict.” Said one: “She saturated us with poetry and filled every day with such lively imagination.” Ripley adored O’Meara, often addressing her as “Mother.”

  Six months after the earthquake, in the fall of Ripley’s junior year, O’Meara assigned an essay about John Greenleaf Whittier’s poem “Snowbound.” Ripley hated writing compositions and, especially, reading them aloud. O’Meara would cringe at Ripley’s stuttering attempts to recite for his classmates. Knowing that he liked to draw—the evidence was all over his notebooks—she decided to allow him to turn in his assignment in the form of a drawing.

  The next day, Ripley handed in a sketch entitled “The Coming of the Snowstorm Told.” In black-and-white, it conveyed the mood of Whittier’s whiteout: No cloud above, no earth below / a universe of sky and snow! The next day, Ripley arrived early to class and handed O’Meara another drawing, a living-room scene drawn in pencil of Whittier’s snowbound family.

  The drawing had “so much feeling” that O’Meara declared it “a masterpiece” and posted it prominently at the front of the classroom. O’Meara realized she could spare Ripley the mortifying experience of reciting his essays aloud. “You like to draw,” she told him. “Now, when I assign a paper to the class, if you would rather draw a picture, I’ll take the picture as a paper.”

  Ripley would turn in dozens of drawings, from Shakespearean scenes to Longfellow’s village smithy. O’Meara considered Ripley’s art more than just boyish efforts at avoiding essays. He took each assignment seriously, researching the historical details. She’d hang them above the blackboard to use as teaching aids and kept them stacked and numbered in a closet. (The drawings would be lost in a 1921 fire that leveled the school.)

  MEANWHILE, Ripley had begun spending more and more time on the baseball diamond, having discovered an agile, loose-limbed adaptability that earned him time at left field, second base, and even the pitcher’s mound. “He was one of the best ballplayers we ever had,” said a classmate.

  Ripley started playing for local semi-professional “bush league” teams, and let himself dream of one day playing for his favorite team, the New York Giants. But Lillie Belle told her son he was too smart to waste time on art and baseball and encouraged him to choose a trade to pursue after high school—if not sooner. “Get a real job,” she’d say. He earned some money drawing posters and advertisements for one ball team while working various odd jobs—loading fruit and vegetable wagons, painting neighbors’ porches, doing yard work. Some weeks he took home as much as $15.

  By his senior year, he’d found part-time work polishing headstones at Fisher & Kinslow Marble Works, which had crafted the tombstone atop his father’s grave. Old man Fisher, a jolly man in a solemn profession, even let Ripley create a couple of tombstone designs. But Ripley soon quit, rejecting tombstones as “too gloomy.” His mother suggested he consider the ministry while warning that if he insisted on becoming an athlete or an artist he faced the “thoroughly enjoyable prospect of slowly expiring at an early age of starvation.”

  Ripley tried convincing his mother there was money to be made in the popular new phenomenon called comics. The success of Hogan’s Alley, introduced in Joseph Pulitzer’s New York World in 1895 and featuring a bucktoothed, barefoot immigrant known as the Yellow Kid, had ignited a fierce competition for dominance in the new world of the funnies. Comics had since become newspaper staples, luring a new generation of boys toward the newspaper business.

  Santa Rosa’s papers weren’t yet carrying regular comic strips; the Press Democrat lost its cartoonist years earlier. But down in San Francisco, the Bulletin, Chronicle, Call, and Examiner all employed staff artists and illustrators, some earning $1,000 a year or more—drawing pictures for a living.

  With that kind of money in comics, Ripley decided to give it a shot. In late 1907 he mailed a one-panel cartoon to LIFE magazine in New York. The sketch showed a pretty woman standing beside a wooden washtub, steam curling up from the water as she wrings clothes through hand-cranked twin rollers. She wears a thin hint of a contented smile, her hair drawn back in a tight bun, sleeves rolled up, her dress draped to her ankles.

  Playing with homonyms—belle/bell, wringing/ringing—his caption read: “The Village Bell Was Slowly Ringing.” In the bottom right corner he signed “Ripley ’07.”

  WHILE WAITING for LIFE’s reply, Ripley continued drawing cartoons for the school newsletter, The Porcupine, where he had been named “staff artist.” In early 1908, he began working on drawings for his commencement program. Graduation was now less than six months away.

  As high school drew to a close, Ripley posed with the rest of the yearbook staff wearing a new suit and tie his mother had saved for. In this and other photos, it was apparent that Ripley had matured into an oddly striking specimen. With his stuck-out teeth and jutting ears, his long nose and greased-back hair, he had a vaguely Dracula-like appearance. Instead of grotesque, though, he now looked almost menacing. Other high school photos show him with expressions that look variously as if he’s about to snicker, or has a barely contained secret, or is crazy or scared—as though he knows something about you.

  Such facial expressions were often the result of attempting to hide his buckteeth behind constantly pulled-shut lips. But a mouth like Ripley’s simply refused to be hidden. When he laughed or smiled, spoke or ate, teeth spilled out, especially when he stuttered. Letters b, f, and p were particular nuisances, and Ripley frequently wrestled with the choices facing someone who couldn’t afford expensive dentistry. He could avoid the world, crawl into a hole, become a monk or a hermit. Or he could create a defiant “I am who I am” persona. Buoyed by the confidence gained from his artwork and athleticism, he chose the latter.

  It showed in his emerging style of dress and his dimpled and unabashedly toothy smiles in certain photos. No longer a barefoot street rat in overalls, he often wore a white shirt and thin black tie with his new graduation suit. Later, as his income allowed, he would complement the suit with bow ties, hats, and nice shoes—efforts to distract people’s attention, to stand out and be noticed for something other than his catastrophe of teeth.

  One person had seen this self-assured side of Ripley all along. After their childhood days of romping around Santa Rosa, Nell Griffith had watched the real LeRoy Ripley slowly emerge through high school. For his part, Ripley considered Nell his best friend. But in the love letters he’d begun writing he made it clear he was now ready for more.

  SANTA ROSA HIGH’S CLASS of 1908 commencement was held on a warm June night, an overflow crowd spilling out of the auditorium as graduates received their diplomas. It was, as the newspaper put it, “a happy event in the lives of their fathers and mothers,” who clutched copies of the commencement program, its cover featuring a boy in cap and gown, diploma in his hand, drawn and signed “By LeRoy Ripley.”

  Ripley, however, was not among the twenty-eight graduates that night. Despite Miss O’Meara’s best efforts to help him after his father’s death, he had left school that spring. The story he’d tell years later was that it was time to find a job and help his family. One problem with that story is the lack of evidence of gainful employment. Instead, there’s much evidence of baseball playing, with Ripley’s name appearing regularly on the local sports pages through 1908.

  Rumors tittered among classmates. Did he get kicked out? Did he just get bored with it all? Among the nastier rumors was that Ripley was so poor his mother had turned to prostitution. He’d been a mysterious presence in their school. Other kids liked him fine, they just didn’t understand him. Maybe they’d never been able to get past the discomfort of seeing those terrible teeth up close. Maybe they judged him,
unable to dispel memories of the stammering elementary school misfit. Or maybe Ripley was the one who pulled back, not letting others get close.

  “He was modest and shy, but he couldn’t be pushed around,” one classmate said.

  The timid boy had grown into a young man who was far bolder, smarter, and more ambitious than he let on. Not wanting to be viewed as “a goofy kid from a farm town,” as he once put it, he’d already decided to leave the farm town behind. However, even the nearest city seemed beyond his reach.

  “San Francisco was where I wanted to go,” he confessed many years later. “It wasn’t fifty miles away, but it could have been Peking for all the hope I had for ever living there.”

  Yet, when he received good news from New York, those fifty miles suddenly seemed like less.

  LIFE’s editors decided to publish Ripley’s “Village Bell” cartoon, which ran in the June 18 issue of the magazine—five days after his classmates graduated without him. The poised and pretty “Bell,” a dead ringer for Ripley’s mother, appeared in the lower-left corner of page three. A letter soon arrived from New York containing his $8 payment. Amazed that his hobby was worth $8 per drawing, he realized that cartooning might indeed be his way out.

  That summer, Ripley earned the attentions of a patron who would help him leave Santa Rosa, introducing him to the newsman’s life, a life beyond all dreams.

  “A high and narrow string bean of a boy” was Carol Read Ennis’s first impression of LeRoy Ripley. An attractive freelance writer, she visited Santa Rosa in the summer of 1908 to profile Luther Burbank for the San Francisco Call. While renting a room at the Ripley home, Ennis often saw her landlady’s son curled beneath a tree, scribbling in beat-up sketch pads when he was supposed to be weeding the garden.

  But she felt the bucktoothed high-school dropout had “a terrific dynamo of unharnessed energy” and decided to make him her pet project. Just as O’Meara had perceived something special in Ripley, Carol Ennis saw a talent where others saw a fantasist, promise where others saw indolence.

  “Do you know anything about politics, Roy?” Ennis asked him.

  “Not a thing,” he admitted, confessing that what he really cared about was baseball.

  Ennis suggested he work up a series of cartoon panels about the upcoming presidential race. Ripley drew a few political and sports sketches, which Ennis took to San Francisco and began peddling to friends and colleagues.

  By fall, Ripley’s portfolio had reached the desk of Fremont Older, the man who had turned the moribund San Francisco Bulletin into one of the largest papers west of Chicago. Older handed Ripley’s drawings over to his brother-in-law, Hiland L. “Hy” Baggerly, the paper’s sports editor, and in February of 1909 Ripley received a letter. “Just came back in time to receive your cartoons, which are very good,” Baggerly wrote. “They are so good I have decided to give you a trial, providing we can agree upon a salary.” Baggerly offered $8 a week and the promise of a $2 raise “if you make good.”

  “I think you have a great future,” said the editor who helped launch the careers of such pioneering cartoonists as Rube Goldberg and Thomas “Tad” Dorgan.

  Though he’d later claim to have started his newspaper career at age sixteen, Ripley was about to turn nineteen. Lacking a diploma or any prospects, he willingly hung up his baseball mitt and wrote to tell Baggerly he was “tickled.” He would save Baggerly’s letter the rest of his days, and Ennis would remain a lifelong friend.

  The Press Democrat soon published a brief item, headlined ROY RIPLEY IS A STAFF ARTIST NOW. He would never live in Santa Rosa again.

  WHEN SANTA ROSANS visited San Francisco, though traveling fifty miles south, they called it “going up to the city.” When Ripley went up to the city in 1909, he wore his best clothes—his graduation suit, a huge bow tie, a straw hat perched high atop his head—but still felt like “a gawky youth … a wistful rube.”

  After a Northwest Pacific train ride to Sausalito, he took the ferry past Alcatraz and across the bay to the Embarcadero. From there, walking up Market Street, he stopped at the Block Mercantile Co., a curio shop filled with antique weapons, stuffed mermaids, Asian tools, and a life-size, eerily realistic wooden statue of a Japanese man, which Ripley coveted. Atop Nob Hill, where he had stood dumbstruck three years earlier watching the ruined city smolder, he looked out from the steps of the elegant Fairmont Hotel onto a resurrected San Francisco.

  Since the earthquake and fire, the resilient city by the bay had surged ahead, a new stone-and-brick metropolis replacing the wooden city that had burned to cinders. Even Chinatown had rebuilt, with an effort toward pagoda roofs, paper lanterns, and Oriental architecture, looking more exotic and colorful than before.

  Ripley loved what he saw, even though the only affordable lodging he could find was beneath the city, in a one-room basement apartment on McAllister. The $5 weekly rent would leave just a few dollars a week for food and other basics. He adapted quickly, learning to hop on and off cable cars, wandering through Chinatown, just as he had in Santa Rosa. Though he considered city life to be “thrilling and daring,” his lone fear was losing Nell. She’d worried the big city would change him, but Ripley assured her by letter that he’d only change for the better.

  When he arrived at the three-year-old Bulletin Building off Market Street and reached the top-floor art room, Ripley was told his job was simple: a cartoon a day, if not more. His first professional cartoon ran on his birthday, February 22, 1909: a bucktoothed baseball fan’s head emerges from a flower-shaped baseball. The caption: “A Spring Blossom.” The signature: “Rip ’09.” During his first weeks, he worked tirelessly, producing more than three dozen full-size cartoons and scores of smaller illustrations.

  He even wrote his first article—“By Rip,” said the byline—about a fighter who had caused a stir in New York by breathing pure oxygen between rounds. In sticking to familiar territory, he mostly focused on baseball. When the minor-league San Francisco Seals prevailed in a twenty-four-inning battle against the Oakland Oaks, Ripley sketched Father Time writing in his “Baseball History” book, “This is the greatest yet.”

  Six months into his new job, however, his lack of training as either journalist or artist began to show. His drawings still resembled his high school newsletter work and Ripley worried that his limited knowledge of sports “made the job doubly difficult.” He hadn’t even found his signature yet, still experimenting with “Rip,” “Ripley,” occasionally “R” or “R2.” Coworkers tried to encourage him, but Ripley could tell that his boss, Baggerly, might be having second thoughts.

  AS A CHILD, Ripley’s exposure to art had been limited to the illustrations in his adventure and history books. He received little encouragement at home or at school, and would later say that his youthful art training consisted of teething on a pencil as an infant, drawing on his bedroom walls, and scrawling on his schoolbooks. “Who did I study under?” he’d say when asked who taught him to draw. “I studied under the stars in Santa Rosa.”

  In San Francisco, Ripley was suddenly working alongside—or in the shadow of—cartoonists who were taking the concept of illustrated newspaper entertainment to new levels. At the time, sports photography was still an imperfect format, with photos playing a secondary (and blurry) role to cartoons. Sports cartoonists gave readers a visual summary of last night’s game or a preview of tomorrow’s. Relying heavily on caricature, they also gave intimate portrayals of the personalities of sport.

  Cartoons had migrated to all sections of the newspaper, and a golden era for cartooning was under way. In fact, Ripley arrived in San Francisco shortly after the nation’s first daily “comic strip” had appeared in print. While working in the San Francisco Chronicle’s sports department, Bud Fisher drew a tall, chinless, mustachioed gambler called Mr. A. Mutt. A year later he paired Mutt with a short, bald guy named Jeff. Though it wasn’t yet called Mutt and Jeff, the cartoon was hugely popular and Fisher was soon earning an unheard-of $45 a week at William Randolph He
arst’s San Francisco Examiner.

  Two of Ripley’s predecessors had been lured to New York by larger salaries and readerships. Thomas Aloysius Dorgan, known as “Tad,” had started at the Bulletin at age fourteen, only a year after losing three fingers on his right hand in a freak accident. He now worked for Hearst’s Evening Journal in New York. Tad’s successor at the Bulletin, Rube Goldberg, had also moved to New York, where he earned $50 a week drawing his popular Foolish Questions cartoon. (Example: A father asks his pipe-smoking son, “Son, are you smoking that pipe again?” The son’s reply, “No, Dad, this is a portable kitchenette and I’m frying smelt for dinner.”)

  BELIEVE IT!

  Through the early 1900s Tad coined dozens of American slang terms, including “for crying out loud,” the “cat’s meow,” the “cat’s pajamas,” “hard-boiled,” “drugstore cowboy,” “Yes, we have no bananas,” “twenty-three, Skidoo,” and “as busy as a one-armed paperhanger.”

  San Francisco had become an important training ground for anyone hoping to actually make a living drawing pictures for newspapers. Goldberg later said San Francisco was where he honed his craft, borrowing ideas from others and learning to trust his personality. “Personality is all-important in any creative art,” said the man who would later create Mike and Ike and Boob McNutt. “If you have personality, it will show in your drawing.”

  Ripley worked among other pioneering cartoonists at the Bulletin—Herb Roth, Hype Igoe, and Paul Terry, soon to be household names. Like many cartoonists, Ripley borrowed heavily from techniques that had evolved over the previous decade. Characters “spoke” in overhead balloons; exclamation points meant surprise; question marks meant confusion. Puffs of dust behind someone’s feet meant motion, buzzing z’s meant sleep. Such pioneering devices had become universal by 1909. Still, there was plenty of room for innovation, yet Ripley struggled to find his own ideas and to trust his own sheepish personality.