December 27, 1938, was the paparazzi night of the season. At 17, Brenda Diana Duff Frazier, the original celebutante (Walter Winchell coined the term in her honor), held her coming-out party at the Ritz-Carlton in New York, where she also lived with her mother. Forty waiters were needed simply to uncork and pour champagne for the 1,249 guests. Fifteen private detectives, disguised in white tie and tails, kept an eye on the guests, who brought out the big rocks for Brenda: the Burden pearls, the Rhinelander emeralds, and the Rothschild diamonds. Two orchestras—Emil Coleman’s 24-piece in the ballroom and Alexander Haas’s 6-piece in the Palm Court—played all night. The tabloid press was banned, naturally, so six Daily News spies in rented tuxes snapped photos before being shown the door—all this for the purpose of formally introducing Miss Frazier to society. Beautiful, wealthy, a Life-magazine cover girl, she could have been on the arm of a president’s son or the heir to any fortune in town. Yet she chose, of all things, a cartoonist, and one twice her age.

Photographers snapped intimate shots of Frazier and her reassuring, older suitor. That evening, he was referred to not by his pen name—Peter Arno—but rather the one by which the city’s social and political elite knew him, dating back to his days at Hotchkiss and Yale—Curtis “Curt” Arnoux Peters Jr., son of the late New York Supreme Court justice.

At 34, Arno was handsome, elegant, and famous, *The New Yorker’*s star artist since its founding, in 1925. “Our pathfinder artist,” editor Harold Ross called him, equal in Ross’s eyes to James Thurber and E. B. White and Helen Hokinson in defining his magazine’s voice and style. With a sexually charged wit (which he came by naturally, as one of the era’s notable roués) and the most innovative graphic mind in magazine cartooning, he resuscitated the single-panel cartoon as it was about to go the way of vaudeville and the silent movie. His collections sold enough to put him in penthouses. His audience ranged from Marie Harriman, who showed his work in her Picasso-laden gallery, to fans of CBS Radio’s Adventures of Ellery Queen, on which he guest-starred as an “armchair detective” to help solve the case of “The Gum-Chewing Millionaire.”

Arno the socialite stayed at the Ritz-Carlton until dawn, keeping Frazier company, and was captured in photos holding her hand while the 17-year-old looks utterly exhausted by the event. (She was.) Five nights earlier, Arno the satirist and his friends—publisher Condé Nast and George Balanchine among them—held a well-publicized debut at the nightclub Chez Firehouse for Miss Wilma Baard. A fashion model, Baard had spent much of her childhood on a Hoboken tugboat captained by her father, so reporters at the event dubbed it the debut of “Tugboat Minnie.” “I think most debutantes are dopes,” she told reporters. While Arno and his friends worked the receiving line in shifts, she stood there for hours, saying only of society that it made “my feet hurt.”

Both debuts landed in that week’s Life, which lists a Peter Arno at Chez Firehouse and a Curtis Arnoux Peters Jr. at the Ritz. It captured Arno’s double life perfectly, the satirist who saw the absurdity of his privileged world and the man who needed to sit at the center of it every day.

‘Perhaps Peter Arno and his collaborators said everything there was to say about the boom days in New York that couldn’t be said by a jazz band,” wrote F. Scott Fitzgerald. “A revolution” is how Algonquin Round Table wit Robert Benchley described Arno. “A total original from no tradition in American cartooning,” says the artist Edward Sorel. “Far and away, the best magazine cartoonist ever,” says Hugh Hefner, who courted Arno in the 1950s in hopes that the artist would help establish Playboy, as he had The New Yorker.

In the 1920s, Arno jolted the cartooning world with his deceptively casual, “slapdash” style (it often required multiple revisions to achieve), and his single-line dialogue caption—“the overheard remark,” as Benchley called it. He drew America’s ruling class as unpleasant, unlikable, sometimes awful people, reducing them to pompous, often sexually avaricious, arrogant boobs—not as a class-warrior but as an insider, as one of them. There’s his Walrus, a Teddy Roosevelt-era, mustachioed millionaire, hunting rifles and big-game trophies on the wall, interrupted by his butler: “There’s a burglar prowling about in the Blue Room, sir. Would you care to have a crack at him before I notify the police?” There’s his Dowager (a cougar, in modern terms), leaning over a cornered man at a party, asking, “Whose little husband are you?” In perhaps his most famous cartoon, there’s his party of F.D.R.-hating bluebloods, inviting friends out to the movies with them. “Come along. We’re going to the Trans-Lux to hiss Roosevelt.” Arno captured perfectly the maniacal “traitor to his class” hate that his peers had for F.D.R.

Before Arno, single-panel cartoons were merely illustrations accompanying written jokes. Compared with newspaper “funnies,” where dialogue and imagery combine into a punchy little movie, pre-Arno magazine cartoons were still lifes. Arno ended that. His image led you to the dialogue caption, a visual setup with a verbal punch line, a combination that remains a New Yorker standard to this day. (This month, Regan Arts will publish the first full biography of Arno, by New Yorker cartoonist Michael Maslin.)

“I like to think I did [invent it],” Arno reflected on this style, “but nothing so basically simple could be ‘invented.’ ” Indeed, no. By 1909, Benchley had tried it as a cartoonist at The Harvard Lampoon. But Arno perfected it and popularized it, becoming, as Benchley put it, “the High Priest of the school.”

Arno’s father—Curtis Arnoux Peters Sr.—served as a Tammany-era city attorney in the tax division before turning his political connections into a fortune as a Wall Street corporation lawyer (at the still-with-us white-shoe firm of Shearman & Sterling), a position he held until 1926, when he became a New York Supreme Court justice. Arno’s mother, Edith Maude Theresa Haynes, from London, is recalled in family memory as religious and dour. (The family attended St. Mary the Virgin, an Episcopal church off Times Square.) His witty grandfathers were a serious influence on Arno’s humor, especially in contrast to his strict, ambitious father. Curtis wanted an elite education for his son—who was born on January 8, 1904, in Manhattan and grew up on Central Park West with the nickname “Arnoux” or “Arno”—followed by a career in business or law. Any infraction of behavior was met with physical punishment. “It wasn’t an easy house to grow up in,” says Arno’s daughter, Pat Arno. “He was spanked if he asked for seconds at dinner.”

That is, when Arno was home. After grade school at Berkeley-Irving, on West 83rd Street, his parents shipped him off to Hotchkiss and summer camps. Lonely and shy, he withdrew into music and art. At 12, Arno submitted his drawings to magazines for the first time. All were rejected.

In humor Arno found a voice. “Nothing delighted me more than provoking laughter with funny stories,” Arno recalled in notes for his unfinished memoir (published in Cartoonist Profiles magazine in 1974). “The shyness and unsureness induced by father’s brutality were overcome by this means…. My father would sometimes overhear me using essential cuss words for the jokes, and ‘box my ears’ so thoroughly that I sometimes couldn’t hear for three days afterwards” (emphasis Arno’s).

In 1922, Arno, six feet one inch, 155 pounds, entered Yale. His circle, dubbed “the lower element of Durfee Hall” by their scolding dean, included John Hay “Jock” Whitney, writer Lucius Beebe, Rudy Vallee, Avery Rockefeller, actor John Hoyt, and later Charles Stanley Sackett—“Uncle Stanley,” inspiration for one of Arno’s best-loved characters. During Prohibition, Beebe kept a fully stocked bar in his rooms. The class of 1926’s defining contribution to Yale history consists of ending mandatory chapel attendance on campus.

Arno and Vallee’s band, the Yale Collegians, played society parties and the Bull Dog Grille, with Arno—who was also busy drawing for The Yale Record—on piano and Vallee on sax. Vallee wanted to sing, but Arno, in a decision that hints at why he was the great cartoonist of his generation and not the great bandleader, vetoed it. On road trips they sought out speakeasies, crashed debutante balls, got bounced from Roseland (“home of clean dancing”), and slept a dozen to a cheap hotel room. Houses of ill repute were not out of the question for Arno, who once paid in trade by playing piano. Arno fondly recalled these days in his memoir notes: “Lived life to the full.”

Curtis senior felt differently, writing to his son, “Your actions and words the last six months have wholly disgusted me.” He, however, was recently divorced from Edith for a woman 16 years younger. On a visit home in January 1923, midway through his freshman year, Arno returned his father’s scorn. “The last time I saw you when I had you to the theatre,” Curtis wrote his son on his firm’s stationery, “you insulted my wife and myself by refusing to walk with us during the intermission…. Under the circumstances, and wholly by reason of your actions, I shall expect you as soon as possible to make other arrangements and get your money either from your own efforts or from those with whom you care to associate with more.” Barely 19, Arno was cut off.

Some have assumed that Arno changed his name to protect his family. “No,” says Caren Ratcliffe, Arno’s niece. “He disowned my grandfather. Uncle Peter wanted nothing to do with him.”

“I wanted my own identity,” Arno said publicly, and privately wrote, “It started, after boyhood and adolescent days of compulsive, incessant drawing on my own, with a drive to excel. This was undoubtedly to show my father that I could be greater than he. Eventually I was.”

His Yale days prematurely over, Arno joined shimmy queen Gilda Gray’s band at her club, Picadilly Rendezvous (when it wasn’t padlocked by Prohibition agents). He lived in Greenwich Village and supported himself as a mural painter and a musician. He submitted drawings to Life, Judge, and The New York World—all rejected. “I was a painter at heart,” he said of his cartoons’ bold blacks and stark lighting, which editors called “too violent.”

In 1924’s cartooning world, Arno was a misfit. The gold standard was *Life’*s Gibson Girls, beautiful Progressive Era ladies who kept men at a distance with prim looks and wry bromides. “Cartoons were polite,” Sorel says. “You had Charles Dana Gibson at Life, whose old millionaires were avuncular, his Gibson Girls decorous. Arno saw young people in that social class as hedonists, playboys, men and women hot to trot. His old plutocrats were far from lovable. He was lucky The New Yorker came along.” And vice versa. “I was the luckiest son of a bitch alive,” Harold Ross once wrote about *The New Yorker’*s early days. “Within a year White, Thurber, Arno, and Hokinson had shown up out of nowhere.”

The New Yorker debuted in February of 1925. That May, Arno submitted a batch of drawings, and back came his first acceptance—with $30. Ross bought more and soon invited Arno in for a meeting. The two men needed each other. Ross, 32, had spent two years seeking funding for his magazine; many of his Algonquin friends promised to contribute, but few did, and some predicted failure. At 21, Arno was a kid, talented and hungry to work. His casual style did not put Ross off—as an ex-newspaperman, he preferred it. Arno’s work shared the newspaper funnies’ unrefined look, but it rose above their puns and slapstick. “Situations should be plausible,” Ross instructed his editors. “Ideas should be literal and show how, unconsciously by their speech and acts, individuals of every New York type show up their hypocrisies, insincerities, false fads, and absurd characteristics.”

To Arno, Ross was validation after years of rejection and boxed ears. For once, an older man reached out to tell him he was valued, not embarrassing. They drank together and once visited Polly Adler’s brothel, where—his defenders insist—Ross only read manuscripts. Arno, most likely, was not there to draw. “Ross was often in Arno’s evening company, especially in the first years,” Thurber wrote in The Years with Ross, his often hilarious account of the magazine’s beginnings, adding that Arno was also “one of the few contributors that Ross didn’t mind confronting personally when he had a bone to pick with him.”

And through the years they would spar creatively over Arno’s use of nudity and his fury when office wits re-wrote his precisely worded captions. The first Arno drawing Ross published, in the June 20, 1925, issue, shows a top-hatted man and his date crossing a Manhattan street as two shifty types under a streetlamp eye them. Anyone traversing the city’s grittier streets for that fashionable café or bar late at night knows this moment still. Arno’s figures are unpolished, his skyline angled, with no regard to the typical illustrator’s goal of getting everything just right. Arno combines all sorts of elements that just don’t belong in a proper magazine cartoon.

“Ross was aware that Arno made the magazine,” says Roger Angell, whose mother, Katharine Angell, joined Ross as an editor in 1925. (She would later marry E. B. White, who, like Thurber and Arno, would have so much to do with establishing the young magazine’s tone.) “The whole idea of The New Yorker as a sophisticated young person’s magazine, full of drinking and sex and good times, all came from Arno. It was one of those things people grabbed hold of in the hinterlands and said, ‘Yes, this is what New York is like.’ ” It was, Angell says, “a fairy tale.”

By 1926—the same year that Tammany elevated Curtis Peters Sr. to the State Supreme Court—Arno was breaking out as the magazine’s first true star. In April he introduced the Whoops Sisters, his answer to the Gibson Girls. Life—in those days a humor weekly—had rejected them (before The New Yorker began), and they would have stayed in Arno’s files had not a young staffer, Philip Wylie, spotted them and insisted Arno submit them.

The Whoops Sisters are two middle-aged foulmouths, later named Pansy Smiff and Abagail Flusser, who spout double entendres (“Whoops, I lost me muff!”) as they stumble about tipsy in New York, with their bloomers visible to appalled young men. In a 1927 appearance, the sisters gleefully toboggan through a cemetery, shouting, “Whoops! Mind the tombstone!”

Dorothy Parker was an enthusiastic fan of the Whoops Sisters, which her disapproving friend Edmund Wilson saw as an example of her “cruel and disgusting” sense of humor. But Parker had lots of company, including Benchley and Fitzgerald. Arno didn’t offer Prohibition tut-tutting about their drinking. He celebrated their rudeness. “These, even more than the introduction of the one-line joke, were the red, red revolutionists of the joke world,” Benchley wrote of them, finding the ladies “sinister” and “macabre,” and that, with their arrival, “fifty years of picturized joking in this country toppled over with a crash.”

That’s a bold statement, to be sure. But the sisters’ lewd drinking was unthinkable in newspapers or parlor humor magazines. It was a shock, one akin to Broadway audiences witnessing Harpo Marx honk his car horn and chase blondes across the stage that season in The Cocoanuts, at the Lyric Theatre. Mae West opened her show Pleasure Man (1928) with female impersonators playing the sisters. For Murray Anderson’s Almanac (1929), Noël Coward did the same, contributing a Whoops Sisters drag sketch (with a set and costumes designed by Arno).

The Whoops Sisters made Arno famous, but he saw them as a one-note joke. As he prepared his first collection, Peter Arno’s Parade (1929), for publication, Arno left his hottest property out. Able to create a book without Ross’s general readership in mind, he included nudes, along with revised drawings and captions, and asked William Bolitho, an intellectual of the day, to write the foreword. Bolitho praised Arno’s total dismissal of “social dogma” and “perfect neutrality of moral purpose.”

*The New Republic’*s T. S. Matthews agreed with Bolitho’s assessment. But, like Wilson, that’s why he loathed Arno. Matthews chided his rough drawing and found his moral neutrality “unsettling” and “disturbing.” Benchley did not exaggerate when he called Arno a revolution. Arno opened the door for a much darker world of cartooning: Thurber’s “scrawl” cartoons, full of angry, hateful married couples (who never got happier); Charles Addams’s guillotine humor—it all begins with Arno.

‘Among New Yorker people he was a celebrity,” Angell says, recalling the image Arno cut with his new fiancée, Lois Long. “The two of them personified what people thought The New Yorker was, which was very fortunate. Those things are just great strokes of luck.” Long, all of 23, covered nightlife in her “Tables for Two” column under the pseudonym “Lipstick.” Tall, lanky, a Vassar grad with bobbed hair and a wicked sense of humor, she was a minister’s daughter to Arno’s judge’s son, and she matched him as a hell-raiser. Their raucous affair helped set Ross on permanent scowl regarding office romances. “There were lots of calls to Winchell or some other columnist about nightclub fights,” says Pat Arno of the couple who became her parents, “with my mother calling and saying, ‘Oh, please don’t print that about us,’ trying to keep their names out of the papers.”

A typical Lipstick column appeared on September 12, 1925, as Long recounted a week in which she spotted Adolphe Menjou and Charlie Chaplin at the Plaza café, checked out a Greenwich Village restaurant, the Jumble Shop, where John Dos Passos and playwright John Howard Lawson were regulars, and was caught in a speakeasy raid where a kindly Irish cop let her out a window to the fire escape, telling her, “Kid, you’re too good for this dump.” Returning early in the morning to The New Yorker to write, she liked to work in her slip during summer.

At one point, Ross provided a basement club for his staff, until managing editor Ralph Ingersoll—who would later jump ship for Henry Luce’s Time empire—found Long and Arno in a situation that ended it. “Ingersoll came in one morning and found Arno and me stretched out on the sofa nude and Ross closed the place down,” Long told Thurber’s biographer Harrison Kinney. “Arno and I may have been married to one another by then; I can’t remember. Maybe we began drinking and forgot that we were married and had an apartment to go to.”

In Peter Arno’s Hullabaloo, a collection of cartoons published in 1930, Arno includes a set of racy drawings featuring a dashing couple much like himself and Long. In one, a nude woman, in bed, yells at her sleeping lover: “Wake up, you mutt! We’re getting married to-day.” In a darker drawing from his collection Peter Arno’s Circus, we see a wrecked apartment with the woman cowering and the furious man demanding, “What the hell d’yuh mean, I’m disagreeable?”

The real-life couple married in August of 1927 at Long’s father’s house in Connecticut. Winchell broke the news that Long was pregnant—before she knew. Lois’s friend Lillian Hellman blabbed to Winchell after Long confided to her she might be pregnant. Winchell broke the news a day before Long’s doctor confirmed it. The couple’s daughter, Patricia, was born September 18, 1928.

Arno’s first three collections sold well, allowing the young family to move into an East Side penthouse. Their social circle included New Yorker staffers, the magazine’s owner, Raoul Fleischmann, publishers Condé Nast and Henry Luce, actress Kay Francis (Long’s former roommate), and some of the city’s financial powers. “Once my mother was having trouble with her Plymouth,” says Pat Arno, “and Walter Chrysler took off his evening coat, rolled up his sleeves, and fixed it himself.”

The Arnos had a front-row seat to a new social world, this “café society,” in which traditional society, the arts, bohemia, bootleggers, and new money came together, to rival the pre-war, Edith Wharton-era social world. “But the blending of the bright, gay, vigorous elements began then,” Fitzgerald wrote in his essay “My Lost City.” “Many of Peter Arno’s people would have been meaningless to the citizen of 1920…. For the first time there appeared a society a little livelier than the solid mahogany dinner parties of Emily Price Post. If this society produced the cocktail party, it also evolved Park Avenue wit.” Arno was that wit. Café society inspired his greatest work, offering him a gold mine of cluelessness and pomposity.

‘I’m going to kill Peter Arno right now,” said a pajama-clad Cornelius Vanderbilt Jr., (unloaded) pistol in hand, on finding his wife, Mary, in the arms of Arno. The artist sprang off the porch of Vanderbilt’s home in Reno and into the Nevada desert, until he out-ran Vanderbilt and got to his own house.

In June 1931, Arno had gone west for a Reno divorce from Long (she also filed for divorce), their tempers (mostly his) having ended the marriage. He soon got involved with Mrs. Vanderbilt, who, however, was living in Nevada with her husband and was not known to be seeking a divorce. Fortunately for the serious historian, Vanderbilt, who sank a great deal of money into publishing ventures hoping to be the new Hearst, spoke to a number of reporters on his near shooting of the cartoonist. “I never hired a gunman to get Arno,” he told reporters. “And I never said I would.”

The fracas set the tone in the 1930s for Arno, who is, bar none, the most tabloid-friendly cartoonist America has ever known. Arno was at the center of a number of “brutal café society brawls,” as snickering columnists called them. And the men with whom he tussled were almost exclusively old-money scions—Vanderbilt, Drexel Biddle Steel at the Embassy Club in Hollywood, and President Roosevelt’s son Franklin junior at La Conga. In fistfights or cartoons, the need to show these people up burned in Arno.

On December 17, 1933, Curtis senior died, with no serious rapprochement between father and son. In 1924, Arno had found himself half-brother to Judge Peters’s new daughter, Constance, 20 years younger than her brother. Now Arno’s father left him $20,000, a sliver of his $750,457 fortune. (The bulk of the judge’s estate went to his daughter and second wife.) “I was a little sore about it at the time,” Arno jotted in his memoir notes. “But the years have proved that a lot of money would probably have destroyed the incentive to work.”

Whatever the turbulence of his personal life, Arno was peaking creatively. By 1935 he knew that café society was a clown show. The “gay, vigorous elements” Fitzgerald recalled were now a tacky whirl of celebrity hounds and tabloid press. In that year’s For Members Only, Arno’s most ambitious collection, he eviscerates the era’s manufactured, fake stars—predecessors of those still on display every day on TMZ and “Page Six.” Forced smiles, manic eyes caught in paparazzi flashbulbs, the vapid rich meeting the desperate-to-be-rich—a New York we all know well.

Here again, Arno moves outside the magazine’s strictures, presenting art without caption, re-inventing the old full-paragraph caption (to parody the hot-type gossip rags of the day), and offering still more nudes. In one classic, he draws the Dowager and the Walrus taking a bath together, trying to maintain their full, imperious dignity even there.

Joseph Mitchell tried to get to the source of Arno’s anger while interviewing him in his studio, at 15 East 56th Street, for a 1937 World-Telegram article. “At no time in the history of the world,” Arno replied, “have there been so many damned morons gathered together in one place as New York right now. Any night in the big night clubs. The town squirms with them. Vain little girls with more alcohol in their brains than sense.... You don’t do good work of this sort unless you’re mad at something.”

Mad as Arno was, who was he kidding? He still had to be at the center of it, and always with a “vain little girl” on his arm. In 1934 he married debutante Mary “Timmie” Livingston Lansing, a lovely, intelligent young woman from Connecticut. Timmie was neither vain nor senseless, but Arno quickly strayed. By 1937 she felt that the marriage was struggling. In 1938 she took an “indefinite” vacation to Europe. One reason, but most likely not the only one, was that year’s debutante No. 1, Brenda Frazier. At 17, Frazier made the cover of Life and took up permanent residency in the city’s gossip columns. Rich, beautiful … but after that, her résumé thinned a bit. Arno knew her as early as October 28, 1938, when he agreed to play the Sun King, Louis XIV, at a Waldorf-Astoria charity ball. Sixty-eight debutantes played the ladies of his court; one was Frazier.

“She loved Peter Arno,” Frazier’s psychiatrist told her biographer, Gioia Diliberto. “She had a wonderful relationship with him. He was demanding, there was a mean streak in him, but he still was quite nice to her, and gave her fulfillment.” Timmie filed for divorce, uncontested. “I asked why he divorced Timmie,” Pat Arno says. “All he said was ‘I didn’t want to hurt her.’”

On January 27, 1939, a month after Frazier’s debut, Timmie, and other readers of the New York Post, awoke to a provocative headline: PETER ARNO JAILS 3 FOR BLACKMAILING. Three men—the building superintendent of Arno’s former 56th Street apartment, Paul Weckholm, and two accomplices, John Wingate and George Pusaey—had contacted Arno about an obscene photo, in which Arno appeared, found in the trash. For a “reward,” Arno could have the photo back.

Simply put, the three men had chosen the wrong cartoonist to blackmail. First, Arno loved a fight. Second, the town’s leading scandal magnet obviously felt he had little to fear from a risqué photo. And third, Arno was an avid gun collector. So he invited their contact man over for a chat.

As The New York Times reported, “Wingate was trapped by Mr. Arno when he called with the picture at the cartoonist’s apartment at 128 Central Park South. The arrest of the two others followed admissions Wingate had made to Mr. Arno and detectives.” Seven other copies of the photo were recovered, and the plotters all pleaded guilty.

None of this mattered to Brenda’s mother, apparently, as Frazier and Arno remained the “It couple” of 1939. La Conga was a regular spot, and Brenda was an early booster of house bandleader Desi Arnaz and his popular “conga lines.” So was Arno’s old friend Polly Adler, the madam, who urged her girls to take their dates to see Arnaz.

“Strange that my first best two girl friends in New York came from poles apart,” recalled Arnaz in his autobiography, “Brenda Frazier, the number-one debutante and Polly Adler, the number-one madam. Between the two of them and from different sources, they sure brought a lot of people into La Conga.” Not so strange, given the one thing Frazier and Adler had in common—Arno’s sex life. Arnaz and Arno liked dropping in at Adler’s together around four A.M. after his late show, or running down to Atlantic City in Arno’s Duesenberg.

At an after-show party at La Conga for Too Many Girls, Arnaz’s Broadway debut, Adler strolled up to Arnaz’s table, where he sat with Arno, Frazier, Mr. and Mrs. Richard Rodgers, Lorenz Hart, George Abbott, and Dorothy Kilgallen. “Cuban, you are the biggest fucking hit in town!” Adler announced, tossing down all the early editions with the show’s rave reviews. When Mrs. Rodgers politely asked who this lady was, Arnaz struggled for words. Arno gallantly explained to Mrs. Rodgers, “She’s Polly Adler, the greatest madam in the world and a very good friend of ours.”

Frazier and Arno had a last headline-grabbing night out when they stopped in at La Conga around three A.M. on June 29, 1939. Actor Bruce Cabot and Franklin Roosevelt Jr. came in, with Cabot asking why Frazier was being dismissive about the possibility of appearing in a movie with him. Arno explained why and, as George Ross’s syndicated “In New York” column put it, “referred sardonically to the four sons of the First Family. And Franklin D. Jr. referred sardonically to other things.” They exchanged words or shoves (depending on the gossip column you read) before cowboy actor Hoot Gibson broke it up.

That September, Germany invaded Poland, and café-society brawls seemed even more ridiculous than they already were. By January 1940, Winchell had announced that Frazier and Arno had split up, and that “Mr. Arno is squiring Carmen Miranda, who brings along an interpreter to keep it respectable.” F.D.R. signed the Selective Training and Service Act—the draft—into law, and war seemed inevitable. “We can handle the text, that’s easy,” Harold Ross said, as he thought about the more serious wartime editorial direction to come. “But I worry about the cartoons.”

Arno answered Ross’s concerns with one of the best-known cartoons of the era. Arno’s March 1, 1941, drawing was an image of a plane crash, with a pilot parachuting down in the background and dismayed officers running toward the wreckage. A civilian engineer, blueprint rolled up under his arm, casually walks away, utterly indifferent to the near fatality behind him. “Well, back to the old drawing board,” he says. A catchphrase still heard today, it summed up the pre-war jitters of Americans perfectly.

In 1942, Arno dated his last “Debutante of the Year,” Oona O’Neill, 17-year-old daughter of Eugene O’Neill and future wife of Charlie Chaplin. “Oona only slept with two men before she married Chaplin,” says her biographer, Jane Scovell—“Peter Arno and Orson Welles. She was looking for older men, some sort of validation from them.”

The affair did not last long. In photos, the contrasts between the jowly, hard-living 38-year-old playboy and the teenage Oona are striking. Was he now his own Walrus? Like his father, dating a woman half his age? If Arno had fears of self-parody, Rudy Vallee confirmed them. In Preston Sturges’s The Palm Beach Story (1942), Vallee hilariously skewered their Yale Collegian days, playing a Jazz Age fop serenading Claudette Colbert and failing.

For the 1944 New Year’s New Yorker cover, Arno revisited his 1929 New Year’s Eve cover, in which his Stanley (based on his old friend Stanley Sackett), ostensibly too drunk to kiss his date, appeared as a blotto poster boy for a blotto era. This time, Stanley and his much, much younger date are cold sober. All around them, young men in uniform kiss their girls, but Stanley and his date barely acknowledge each other. He checks his watch, ready to leave; she sits up, icy, stiff, staring off into the distance, clearly missing someone not there—and possibly never coming back.

Arno knew that feeling. A close friend, naval reservist and artist McClelland Barclay, went missing in the Solomon Islands in July of 1943. For Arno, the party was over. Café society was done. “These people have ceased to exist since the war or have gone underground,” said Arno. “I refuse to stay around and watch them crawl out again when peace comes. I don’t want to see them beating their brains out any more in champagne traps.”

After the war, Arno did not suffer a midlife crisis so much as a midlife calm. He had proved himself to the world, repeatedly. His father had been dead a dozen years, and Arno was still on good terms with his mother. He was distant, at best, from his ex-wives and daughter, Pat. But now he began years of analysis, eventually moving to Port Chester, up in Westchester County, where he slowly welcomed family into his life as an uncle and grandfather. The anger faded. “My idea of luxury used to be a high penthouse and twenty five tailored suits,” Arno wrote in his memoir notes. “Now in the country, with the city penthouse a shabby substitute, my idea of luxury is having three pencil-sharpeners in different parts of the house.”

Harold Ross died in December 1951. Earlier that year, when Arno published Peter Arno’s Ladies & Gentlemen, a collection encompassing their years together, he dedicated it to Ross—the only one of his books to include such a tribute. Family members recall Arno, in the 60s, in a long-term relationship with a Westchester woman—not a teen deb, an adult. She is remembered as doting, stocky, with children. Arno acted fatherly toward them in a way he had never been with Pat.

In Esquire in 1966, Brenda Frazier appeared in a ghastly photo by Diane Arbus, propped up in bed, wrapped in furs, cigarette in hand, clinging to glamour. Arno preferred to age with humor. In a cartoon from that same year, Arno depicted a middle-aged couple, she sitting on his lap, a vampish rose in her mouth; a chilled bottle of champagne sits next to them. On the phone, he says, “We’re watching an old Pola Negri picture.”

Toward the end, it was clear that decades of all-night drinking and smoking in dark clubs had taken their toll. During the 1960s, Arno battled emphysema and lung cancer. Few saw him, and in his last years, doctors put him on an oxygen tank. “He had been so handsome in his youth,” says Arno’s niece, Caren Ratcliffe. “I don’t think he wanted to be seen like that. When my mother told me Uncle Peter was on an oxygen tank, I couldn’t imagine it.”

Arno’s mother died on January 31, 1968, at age 87. Arno died three weeks later, on February 22, at age 64. Reporters called Pat Arno, asking for an anecdote or two about her famous father. She simply replied, “None are repeatable.” Arno’s last cover for The New Yorker appeared in June, a polar bear and its cub in the zoo, parent and child, peacefully rubbing noses, a polar bear’s kiss for its offspring—a lifetime away from top hats and nightclubs.