Seven years ago, on the day that Matthew Diffee sold his first cartoon to The New Yorker, he waited for the elevator to arrive on the 12th floor of 20 West 43rd St., the magazine’s former office building. When the heavy gold doors slid open, the legendary cartoonist George Booth, a contributor to the magazine for nearly three decades, walked out. Diffee recognized him from having memorized his name and face in The New Yorker’s first Cartoon Issue. “Mr. Booth!” he shouted. “I just sold my first cartoon!” In his lilting Missourian accent, 71-year-old Booth murmured, “Welcome aboard,” and shook the younger artist’s hand.

Diffee told me this story the first time that I talked with him. Relaying the details of the day, he showed no awareness that his rise to prominence might coincide with the decreased visibility of beloved old timers like Booth. In fact, an informal survey of the last six months reveals that the magazine regularly publishes Diffee’s work, while older artists like Booth appear much less often. As Warren St. John wrote recently in The New York Times: “The move to bring in new talent to the magazine is not tension-free. Space and money taken up by newcomers is lost for the old guard, who are popular with many readers.” Until I mentioned it, Diffee had not considered what others, including the Times, suggest: There seems to be a phasing out of the older generation, that the more senior artists may feel pressure to be “hip,” that some may suffer from a loss of artistic confidence, not to mention income. “I think it’s sad,” I told him. “A computer doesn’t belong in a George Booth cartoon.” He nodded in agreement. Over the next two weeks, as I tagged along with Diffee, I uncovered an unsettling reality, one that impacts the lives and art of the people involved. The New Yorker cartoon legacy is not only changing hands, it is jettisoning its own history as it goes.

Diffee and Booth’s paths to cartooning differ wildly. While Diffee doesn’t typify the entire younger generation, or Booth the old guard, their lives and work do suggest certain generalizations about the making of artists, now and then.

Diffee’s route to cartooning and The New Yorker was eerily serendipitous. “I should mention that cartooning is not a part of this story until the very end,” he explained to me. Growing up in a small town in Texas, he wanted to be a wildlife artist, along the lines of John James Audubon or Robert Bateman. In South Carolina, where he attended college, he gravitated to the art program, and spent most of his time drawing and painting. Upon graduating, he eventually moved to the Northeast, selling paintings, teaching art and writing, and performing stand-up comedy.

He ended up in Boston, which is where, late one night, he happened to catch a Nightline feature on The New Yorker cartoonists. A snob on both the humor and the art fronts, Diffee had never considered cartooning to be a laudable art form. Yet the program so excited him that he ran out and bought the December Cartoon Issue and pored over its pages. He memorized the names and faces of all the artists pictured. Upon discovering an advertisement for a contest sponsored by the Algonquin Hotel and The New Yorker, he drew up three cartoons with hotel themes and submitted them. He landed in first place. (The two other finalists had been trying to break into the magazine for years.) At the awards ceremony in Manhattan, the magazine’s cartoon editor, Robert Mankoff, suggested that he begin submitting cartoons to the magazine regularly. He went home to Boston, drew up three sketches, and mailed them in. The next week, he drew three more. The magazine bought one, giving the artist the right to submit in person, so he took the train to New York. Meeting with Diffee in The New Yorker office, Mankoff offered a little professional advice: cartoonists typically do 10 to 15 drawings a week, not three. Diffee upped his production, moved to the Big Apple and has been a professional cartoonist ever since.

In a way, Diffee didn’t find cartooning — cartooning found him. The average age of the cartoonists in the Cartoon Issue photo he studied hovers around 60. In the Nightline special, Ted Koppel mingles with mostly gray-haired men in black tie. When I watched the television show that attracted Diffee to the contest, I had the feeling that, at a time when the magazine desperately needed new blood, the long arm of The New Yorker reached knowingly up the Northeast corridor to find its next generation: a wayward son to whom it had never occurred to become a cartoonist. “I don’t know why I never thought of it before. The combination of humor writing and drawing is perfect for me,” he says with some bewilderment. “I do feel I am where I’m supposed to be.”

Diffee’s images stand out for their high-quality draftsmanship. Done in soft pencil, his drawings are truer to life than many of the other cartoons. He often juxtaposes incongruous elements for humor’s sake, like Girl Scouts selling crack, or a man performing an interpretive dance in an auto salvage yard. Other cartoons capture a kind of wholesome Americana. In one, a suburban father waits at an open front door, holding a coffee mug and newspaper. A young boy standing casually on the steps asks, “Can Lucy come out and date?” Another depicts a church drawn in simple, elegant lines. The sign in the yard reads, “NO SHIRT NO SHOES NO SALVATION.”

Diffee’s own character and history, the good-natured kid from Texas, shine through this work. But in other cartoons, there is a dissonance between the artist and the content. These themes, which include consultants, breast cancer awareness, boy bands and power ballads, seem more like a guy trying to appeal to an urban population. There may be a reason why his work doesn’t always look like himself: His style was partly appropriated; it was a choice he pulled from The New Yorker’s of old. After he sold his first cartoon, he researched classic cartoonists such as Charles Saxon, Charles Addams and George Price, and modeled his work after theirs. Add the stand-up comedy text, and sometimes it succeeds gloriously. Other times, the result is a jarring jumble of choices that reflect today’s retro trends, snappy humor and instant processes.

In contrast, Booth mellowed into his voice over time. He wanted to be a cartoonist from the age of three, yet he didn’t sell his first cartoon to The New Yorker until the age of 43. “I think I had been growing up,” he explained to the Times in 1981. Booth started out trying to draw New York. Bad move. “I’m anything but sophisticated,” he told me over the phone. “I’m country. It’s an old story, but you’ve got to be yourself.” This realization came on a visit to his hometown in Fairfax, Mo., when he happened to draw an old hotel from the 1920s. He drew the tin ceiling, and a light bulb hanging down. To him it was home, but to New Yorkers it was a railroad apartment. When he let go of any locale and drew what he felt like — scenes from his Corn Belt upbringing — his career took off. Essentially, Booth had time to find himself in his art before he made it big; Diffee’s doing it right in front of us.

One curator described Booth’s idiosyncratic voice as “hope in the midst of what looks like calamity.” Chaos typically reigns in a Booth cartoon. Auto body shops, junkyards and shanty interiors establish the ambiance. Cats and dogs hang about. Characters squabble. Some cartoons express a kind of whimsical absurdity. In one, a band of country folk gathers together with instruments. A pear-shaped conductor atop a soapbox raises his arms. The text reads: “‘From the top — ‘Watermelon Man.’ Let’s sock it out and give Mrs. Ritterhouse a chance to really cook!'” The commentary underneath the humor is anything but light, however. In another cartoon, a raisin-faced old couple squeezes onto a loveseat. “Forty-one years of marriage. That’s a long, long, long learning curve,” the woman says. The text is funny, but their bitter expressions, and the critique of marriage, are more than terrifying.

The snail’s pace of Booth’s artistic evolution — the years of practice, dedication and sheer will to continue — is a track fewer artists have patience for today. Yet just as Booth became his own institution, shaped by his art form and the prestigious umbrella of The New Yorker, Diffee will undoubtedly grow into his voice over time. He’s in the midst of this change right now. When he talks about growing up in a town with little intellectual or cultural life, his stepfather and brother who work in the tire business, and his preference for Texas barbeque and blue grass music — a life as far as possible from The New Yorker — his voice drawls slightly. He seems more Southern, plain old American. But when the topic turns to his recently acquired profession, his tone tightens and becomes more authoritative. His features — angular cheekbones, dark brown frizzy curls, long sideburns, prominent nose and brown eyes that have an exotic tuck in the corners — seem to cohere. As if a cartoonist drew him, he becomes a character, a public personality, before my eyes. “I’m very aware that I’m participating in something important,” he tells me of The New Yorker legacy he has inherited. “I feel privileged to be a part of its history.”

“Versus! Who says its versus?” Mort Gerberg, a tiny firecracker, asked pushing his face toward mine. We were standing on a barely lit stage at PS 122, an East Village venue for dance and theater, where “The Rejection Show” had just ended. Conceived by Diffee and the comedian John Friedman, the once-a-month review features jokes, comic sketches and, most importantly, New Yorker cartoons that have been rejected by the establishment. When the show ended Diffee introduced me to Gerberg, a contributor to the magazine since the sixties and the author of “Cartooning: The Art and the Business,” a book the young guys refer to as “The Bible.” I informed him that I was writing an article on younger versus older cartoonists. My phrasing seemed to have hit a sore spot. “Huh? Who says?” Gerberg continued his jabs, as if we were sparring. “That’s the first thing you said to me, versus.” I tried to jump in, “Talk to me about it, then–” But he steamrolled over my words, “The Times painted it like that. But it’s not really like that,” he said with finality.

He had a point. While most of the performers were under 35, the New Yorker cartoon rejection segment included a white-haired older gentleman, JB Handelsman, who joined Diffee and 33-year old Eric Lewis on stage. Other New Yorker cartoonists spanning six decades, age-wise, filled the house. The event felt like a family reunion, and not at all like a battleground between the old guard and the new.

Still, an underlying tension suffused the show. A self-described team player, Diffee is open to any cartoonist joining in the show, which includes guys who have been selling cartoons since before he was born. He does, however, retain the final say in who performs. Diffee’s not power hungry, but it is his gig, and it has become the “gig of the moment,” in New Yorker cartooning circles. (Mankoff regularly asks which cartoons got laughs that week; the show has even managed to redefine “rejected,” as some cartoons get picked up later for publication.) When artists sense a buzz, especially when those artists regularly face professional rejection — the real kind, not the ironic, PS 122 kind — there’s an inevitable scramble to participate. Yet between them and the exposure, and the affirmation of the laughter and applause, lies a go-getter who’s been in the business a mere seven years. This may be tough to take for the folks who have been around a while.

I wondered if this subtle envy might be the sore spot that I hit in my conversation with Gerberg, who had more to say on the subject of legacy. His glasses, thick panes, reflected the work light that had been turned on at the end of the performance. His eyes appeared ghoulish. “The young guys, like Matt, and Eric, they’ve read my book, and they came up to me, and told me what an honor it was to meet me. That matters, that they respect our work,” he said. His wife, who was even tinier than her husband, patted his arm. “Some of the other guys don’t care,” Mort finished. He then pointed to Handelsman respectfully, “That guy has been around much longer than I have.”

“And what about George Booth?” I asked. He nodded, “George Booth, he’s one of the best. The best of the best.” Gerberg seemed to be gathering an alliance of the old set with his comments, to counteract the largely youthful spectacle that we’d just witnessed.

Perhaps because Diffee and I had also spoken about legacy that week, he alluded to it in the beginning of the cartoon sketch. After mentioning himself and Lewis, he introduced the third performer: “This is JB Handelsman, one of the founding fathers who paved the way for young whipper-snappers like us,” he said. Taking turns, the cartoonists leafed through their portfolio of transparencies, chose one, and placed it on the projector. An image popped onto the white screen, and the artist read the punch line. Diffee’s delivery was low-key; Lewis used funny voices. One of Lewis’ cartoons depicted two pirates sailing by a lesbian mermaid couple in a lover-like clasp. “Arrrr, just our luck,” Lewis growled. Handelsman read with an out-of-breath quality. One of his images portrayed a doctor’s office. “Ask your doctor if Boffo is right for you, and if he says it isn’t, tell him he’s full of crap,” he gasped. The emphasis on crap caused a stir; the crowd giggled. The joke was a hit.

Handelsman had the final say on rejection. Seizing the microphone, which Diffee gracefully relinquished, he whispered into it, “I’d like to thank the editors at The New Yorker for providing me with so many rejections. If you’d like to see more you can come to my house.” Chuckles and applause rippled through the house. Having provided the audience with a glimpse of the camaraderie between the young and the old, the cartoonists returned to their seats.

Later, while walking to an East Village bar for the after-party, Lewis approached me. He’d heard about my article from Diffee. “I will have to tell you about my Obi One, Yoda relationship with Sam,” he said. He was referring to 71-year old cartoonist Sam Gross, whose work is so fresh it appears to have been made by a much younger artist. “He told me to have–” he said, pausing. When he spoke again his voice was high-pitched and awkward, and sounded exactly like Yoda. “‘Patience, my young friend.'” He dropped the voice, adding, “Sam’s given me plenty of advice on the business. He even wrote me a letter of recommendation for RISD.”

Lewis graduated from the Rhode Island School of Design this past May, and intends to support himself as an industrial designer until his cartoon sales pick up. His reverence for Gross partly has to do with his business savvy. Greeting cards, calendars, mugs; these are the means by which Gross survives financially. The older artist told me later that success is “all about royalties,” which allow him to make money, even when he’s doing no work. Advice on how to collect a paycheck from one’s couch may be premature for Lewis, however, who has one main goal: to earn a cartooning contract with The New Yorker, as Diffee did last year.

Gross’s attention undoubtedly offers Lewis artistic affirmation as well. I asked him if he thinks Gross sees himself in his work. In that moment Lewis became serious. “I don’t know,” he replied. “We both draw cats, and we’re certainly both goofy,” he added. To illustrate this goofiness, he described one of Gross’s cartoons. “Do you know the one with the snails and the tape dispenser?” he asked me. “The one that goes, ‘I don’t care if she’s a tape dispenser. I love her,'” he recited the text fondly. I’d come across it the day before, flipping through the 2004 cartoon book. I admitted that it was one of my favorites. “Sam has TWO cartoons in the top ten best of all time. Two!” he continued. Though Gross had long since left the party, Lewis’ reverence made him seem absolutely present.

Later in the evening, however, the old guard was forgotten when Lewis turned to a discussion of the next generation’s ambitions. A pool of red light cast by the “Miller” sign in the bar window illuminated his monologue while a few of the performers stood nearby. “Diffee’s the spearhead of us younger cartoonists. He’s the one with the energy, and all the ideas. He’s our leader,” Lewis explained. Then, in imitation of his friend, he suddenly had all the excitement of a child: “I know! We’ll do a, a, a,” he puffed out his chest, looking remarkably like Pavarotti, “a cartoon op-errr-aaaa!” he joked, his arms raised toward an imaginary audience. The group soared on the waves of possibility.

Diffee towered over us all, a six-foot-something general rallying his troops. A triumphant grin spread slowly across his face. The younger generation, it seemed, was here to stay.

On submissions Tuesday, the traditional day on which the cartoonists turn in their batch of drawings for the week, I met Diffee in the lobby of the Conde Nast Building on West 42nd Street. He led me up to the 27th floor, where Mankoff’s office is nestled into a corner of The New Yorker’s space. The routine is always the same: manila mailing envelopes containing cartoons pile up like snowdrifts outside his door. Those cartoonists who show up in person wait in line for a visit with him. Mankoff looks over their work in less than three minutes while making small talk; hardly enough time to process the images, the text, or even laugh. He keeps a handful of drawings and hands back the rest. Later, he meets with editor David Remnick to decide the final cut. Finally, the artists receive a phone call on Thursday informing them if the magazine bought any of their cartoons. I asked Mankoff’s assistant, Marshall Hopkins, if the day is emotionally difficult. After all, in those few minutes, careers, livelihoods and artistic egos are determined. Hopkins’ eyes widened, “I don’t like it,” he replied, shaking his head. “It all happens so fast, it’s like an audition.”

Under Mankoff, the artistic emphasis in the cartoons changed. Editors of the past emphasized the drawing, and the integral relationship between the text and the image for comic power. The line was “spot on” funny only in combination with the picture. Recently, the text has evolved into punchy one-liners. Much like stand-up comedy scripts, the text holds up when read alone. With less importance placed on the image for laughs, drawing technique has fallen by the wayside. Some say the newer cartoons have less depth, and have lost their art value. In the wake of this artistic evolution, many of the older generation, much to their helplessness, find their work labeled out-of-date by the editors.

“Bud Handelsman is still funny. George Booth is still funny. I’m still funny,” Gerberg told me defensively when I asked him why the old guys were being phased out. “We haven’t changed, we’re still doing the same work, and we’re still funny. What’s changed in this equation? The editor, that’s what has changed,” he said, his voice rising. “I think I can speak for my colleagues when I say that many of them are terribly depressed!” His tone was low-level hysterical.

The Tuesday that I visited The New Yorker’s office, the anxiety in the waiting room vibrated through the cartoonist’s chatty conversation. Mankoff had not yet arrived. Gross and Gerberg occupied chairs. A few younger cartoonists hovered near the door. I sat down beside Handelsman, who was planted on a leather couch. As the conversation progressed, I asked him what it was like to be at the mercy of the editor, decade after decade. “I don’t like being at the mercy of one who hates my guts,” he replied bluntly.

Apparently Handelsman has not been selling well. “I’m going to speak with Bob today. I thought it was time I take a stand. I want to ask him, are you a messenger, or a cartoon editor?” he heaved, his eyes red around the edges. “Not only that — I’m still living, I have to eat,” he told me. “I am being systematically starved.”

For Handelsman, those twenty or so cartoons published each week in the magazine are not about humor. They are about life or death. I asked if he’d branched out, maybe sold other places. He used to sell to Playboy, but that tapered off. And he was too lazy to try elsewhere, or write the book he’d wanted to. Everything depended on this magazine. And to his desperation, The New Yorker and its cartoon editor were not coming through.

When the cartoonists prepared to leave for their traditional post-submissions lunch at Pergola des Artistes on West 46th Street, Handelsman opted to stay behind. “I have to give him hell. I can’t go another week. I have to speak with Mankoff,” he told Diffee and me. The skin on his face puckered and sagged under his eyes, which were bright blue and appeared just on the verge of tearing. His white flyaway hair framed his face. “You should show him the ones that got laughs at ‘The Rejection Show,'” Diffee told him, “Bob asked me what did well, there. Tell him which ones did well.” He sounded almost fatherly. “I plan to show him those,” Handelsman replied, carefully emphasizing each word.

As the group departed for lunch, Handelsman remained behind, his fingers clutching his pack of cartoons.

“I need cartoonists twenty years from now,” Mankoff told me frankly, by way of explaining his need to encourage younger artists. He is concerned with the preservation of the art form. “People get old and die, they just do,” he added.

Diffee had taken me back to the office after all of the cartoonists had left, to speak with his boss about the issue of legacy. He waited outside the waiting room as we chatted. In contrast to the hubbub earlier, the place was silent.

Mankoff has a mane of graying brown hair and eyes that sink into his skull. He espouses heady theories about cartoons. “The world is an alien place,” he philosophized, when I asked him about younger verses older humor. “And the older you get, the more you want to get away from it. But when you are younger, it’s still an alien place, only you want to be in it, and see what it’s like. The fusion of comedy comes when youth meets the world for the first time. There’s an aggressive sexual component to humor, male humor in particular. It’s about getting angry. Humor is the rage of the powerless.”

It was hard to get a word in — Mankoff ran on with little prompting. But I managed to ask if he was suggesting the older cartoonists lose their sense of humor.

“No,” he replied. Then he corrected himself, “Well, you develop your shtick. You find the way you make jokes about the world, and you pretty much ride those tropes for the rest of your life.” I wasn’t quite sure what he meant. Did he think the old guys had lost their senses of humor, or what?

He never elaborated further, but assured me that the magazine still publishes George Booth. And when I asked what about Diffee’s work caught his eye at the contest six years ago, he shrugged. “I don’t know,” he said, “he did something sort of funny, I don’t remember what. So I knew he could be sort of funny, and he could draw. And, I don’t know, he looks weird. So I thought, maybe he could do stuff. It was just a hunch, basically.” He looks weird? My face must have registered a slight shock, because he added that the cartoonist’s work must hold its own, after the initiation into the business.

Later I learned that Mankoff can be flippant about other cartoonist’s careers. Tough to have a boss who is also a cartoonist, I thought.

When Handelsman finally appeared in the restaurant that afternoon, he was twenty minutes late. The waiters had already served the wine, bread and olive oil. Cartoonists of all ages sat around the table. The ancient Gahan Wilson, as legendary a cartoonist as Booth, presided over one end. With his bald head and black turtleneck, he looked like King of Middle Earth. Younger artists filled in seats on the sides. One, Evan Frosch, had yet to sell a cartoon to the magazine, but had been submitting for six months. Another, Paul Noth, sold his first cartoon that day. Diffee sat across from me. Gross and Gerberg filled in other chairs. Handelsman weaved slowly through the restaurant to get to his colleagues, holding on to each chair as he passed. With a glint in his eye, he approached the table. We made eye contact. “I just killed Bob Mankoff!” he blurted out.

The joke was spot on.

The notion of legacy is complicated. Art forms tend to evolve over time, as new blood and ever-shifting social landscapes reshape old mores. A young cartoonist like Diffee can learn from his predecessors, but in the end his greatest task is to look inward and forward. Meanwhile, in an ideal world, the artists who have poured their talents into shaping that tradition should gain more respect over the years, not less. At The New Yorker, this doesn’t seem to be the case. Even the great George Booth feels the pressure.

When we spoke over the phone, early on, Booth told me that he had been discouraged by the younger generation’s work. But now he feels they are doing some wonderful stuff. “They’re more up to date than I am,” he commented. He paused, and continued, “I have to take a look at myself, now.” And then he added, “You have to update yourself, stay aware of what’s happening.” He sounded almost wistful.

Booth described a cartoon in the 2004 book to illustrate his point. He loves to talk about cartoons. He lays out the image so that you have the entire picture in your head, gleefully delivers the punch line, and then laughs to himself for a good thirty seconds. “In one cartoon, from the 1920’s, there are two ladies on an ocean liner. The sea is absolutely calm. Two officers are coming out of the hold,” he built the scene slowly for me, and then dropped the joke. “And one of the ladies says to the captain, ‘Aren’t you going to toot?'” he said, chuckling to himself. I waited, on my end of the line, for him to finish his thought. “You see? That was funny, in the 1920s. It’s a wonderful historical record.” he concluded.

Humor changes. This is the point he is making, but not saying.

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