Cartoonist captures modern life

NEW YORK – Into the swirl of Times Square walks a Texan carrying a batch of cartoons. He is bound for the halls of America’s magazine empire, a place where one raised eyebrow from the right editor could send him out of luck, out of sorts and out of this week’s paycheck.

Matthew Diffee, 35, turns into the Conde Nast building, home to an illustrious stable of magazines. Vogue. Architectural Digest. It happens here.

As he makes his way to the elevator, the walls of the lobby vibrate with the passing of a subway train, making the building feel alive, trembling, about to burst with creative energy.

The wiry-haired, angular Texan is headed to the offices of The New Yorker, where he hopes to sell one of his wry pen-and-ink comments on modern life. Odds are, he will. He’s known as a rising star, a cutting-edge humorist and one of the “young guys” adding fresh viewpoints at the 80-year-old magazine.

Floor after floor, the elevator carries him upward, giving him time to contemplate the odd mathematics of success.

Diffee is learning that success involves a lot of failure. Repeated failure. Constant failure. Certain failure. Over and over, he fails on his trip toward the top.

For decades, cartoonists have gone every Tuesday to submit their gags to the weekly New Yorker.

On a Tuesday in February, the hall outside the cartoon editor’s office is filled with, well, a gaggle of cartoonists.

Each clutches batches of 10 or more single-panel cartoons.

In six years, Diffee, the son of a former Braniff Airways pilot, has penned more than 3,000 cartoons for The New Yorker. Almost all have been rejected.

In his first year, Diffee submitted 15 cartoons a week. Only four were bought.

That means 99.5 percent of his work didn’t capture the heart and mind of the magazine’s legendary cartoon editor, Robert Mankoff.

Now, considered to be at the top of his game, Diffee submits 10 a week and usually sells one. That means 90 percent of his cartoons are rejected.

An undercurrent of anxiety runs through the waiting cartoonists. It’s as subtle as the subway rattle but just as present.

What, if any, will Mankoff buy?

“A psychiatrist to a patient: “These feelings of inadequacy are common among the inadequate.” – from a Diffee cartoon in The New Yorker

Diffee’s realistically rendered work finds ticklish spots in uncommon places. His cartoons cover business ethics, the demise of the family, break-up lines, the hopes of shallow young women and the greed of rich old men. And more.

For something to be funny, it should have an element of truth, Diffee says.

In one of Diffee’s New Yorker cartoons, a waiter is issuing an accurate warning: “Careful, these plates are extremely dirty.”

In another, a man at a bar is making an astute assessment of his life: “I’m a stay-at-work dad.”

Like many of his fellow New Yorker cartoonists, Diffee is a quiet, smart guy who closely watches the world around him.

“Cartoonists are observers, not participators,” says another young New Yorker cartoonist, Drew Dernavich. “Then they go home and participate by writing.”

Diffee was always the funny kid in elementary school in Denton, Texas. He always drew. He fell asleep at night in his upstairs bedroom over the family’s music room, where his father practiced bluegrass. The creative influences were there.

After studying art and creative writing in college in South Carolina, Diffee went on to a remarkable career in fun. He was a camp counselor, an art teacher, an abstract expressionist artist, a stand-up comedian, a documentary maker, a player of banjo, fiddle and dobro, a street juggler and even a “joggler,” a hybrid sport combining jogging and juggling.

A New Yorker caption contest caught Diffee’s attention in 1999. The drawing was of a couple inside a hotel room eyeing the “Do Not Disturb” sign hanging on the doorknob. Diffee’s winning caption: “Oh, great. I guess that means we’re stuck in here.”

That’s the path that brought him to the 20th floor of Conde Nast, along with the dozen or so other guys – mostly guys – who are submitting in person rather than by fax.

A lone woman waits to show Mankoff her work. “It’s like juggling,” Diffee says. “It’s a nerdy endeavor that women don’t tend to get involved in. I mean, like model trains.”

Each hopeful gets about one minute of face time while Mankoff looks at their cartoons.

The cartoon editor never laughs.

Depressed man at bar: “I feel like a man trapped in a woman’s salary.”

– from a Diffee cartoon in The New Yorker

The tall Texan sits down in front of the powerful editor’s desk, presenting his week’s labors to the man who claims to carry a humor license that entitles him to judge.

If anyone knows “funny,” it’s Mankoff. He’s written more than 700 cartoons for The New Yorker, he’s edited several collections of New Yorker cartoons, he’s authored a book on cartooning, and he founded the Cartoon Bank ( www.cartoonbank.com), a large computerized archive of New Yorker cartoons.

Mankoff shakes his shoulder-length mane of curly gray hair and asks Diffee where he gets ideas for characters.

“Well, we did live down the street from a family of professional wrestlers,” Diffee says by wayward way of explanation, describing the famed Von Erich family that once resided near his former home.

At this point the conversation breaks down further and morphs into one about one of two Rubik’s Cubes on Mankoff’s desk. Then it veers swiftly into a talk about juggling.

Mankoff demonstrates how he can juggle one thing at a time, tossing a Rubik’s Cube up in the air.

He flips through Diffee’s 10 cartoons.

On top is this one: Two pretty, young women sit at a café. The caption reads: “I love sleeping beneath the stars.”

Next is this: A crowd of angels stand on clouds. One looks at the other and says: “I don’t know a soul here.”

“That’s a gentle one,” Diffee says of the angels. “I’m known as risque, an envelope-pusher. But those are the cartoons that Bob picks. In some ways, he decides my comic voice.”

The meeting is over. Mankoff grabs a few of Diffee’s cartoons to share with New Yorker editor David Remnick, who will help decide which to buy.

“Matt’s fresh,” Mankoff says of Diffee’s work. His style is distinct, he can be a little racy, he’s a new voice in a magazine that is, like all publications, looking to attract young readers.

Diffee won’t know for days if any of his work is bought.

Patient to psychiatrist: “I have an imaginary friend. He’s a real person – he just isn’t really my friend.”

– from a Diffee cartoon in The New Yorker

In the Brooklyn loft where he writes, draws, sleeps and dreams is a yellow legal pad filled with the workings of Diffee’s mind.

The handwritten half-ideas include these notes:

“Zen and the art of exploiting Buddhism.”

“Sheep: I wish I brought a sweater.”

“Start losing money from home.”

“Lose money. Ask me how.”

“Fifteen minutes of shame.”

Ideas evolve on the page. “Road Rage” becomes “River Rage.” A list of ship names begins with “SS Minnow” and ends with “SS Trustfund.”

“The best ones come out of nowhere. You can work every day for a month, and the best ones come out of the blue,” Diffee says.

He then draws for a few hours every day.

His contemporary viewpoint is balanced by his occasional use of the classic setups of desert islands and bar scenes.

“We love to include the old genre,” Diffee says. “It’s like Norah Jones or Gillian Welch. They are new, but they are doing what’s classic.”

His friend Chad Covert Darbyshire, a New Yorker cartoonist from Austin, Texas, laughs when Diffee says this.

“Norah Jones! No, I think you are more like Cyndi Lauper on her comeback tour. You are more Farm Aid!”

Much laughter ensues, but cartooning is serious business.

A cartoon sells to the “New Yorker” for about $1,300.

“You cannot make a living on the initial sell,” says Sam Gross, a New Yorker cartoonist since 1969. “You sell reprints and get royalties. You sell something over and over and over.”

Gross sold one cartoon to the former National Lampoon magazine 35 years ago, and its resale has since earned him $100,000. The cartoon: A couple in a restaurant sits near a sign that says frogs’ legs are the special. The kitchen doors swing open and out rolls a legless little frog pushing himself in a sort of frog wheelchair.

Diffee is selling reprints already. One, a cartoon of Che Guevara wearing a Bart Simpson T-shirt, has sold 25 times, drawing, as it were, on the popularity of T-shirts depicting the Cuban revolutionary leader.

Not that Diffee is particularly revolutionary or anti-revolutionary. He’s also drawn cartoons used in Altoids ads.

Recently, he’s become known for his ability to celebrate his own rejections.

Woman says to a man working on a laptop next to her in bed: “Honey, you are sleepworking again.”

– from a Diffee cartoon in “The New Yorker”

The theater in New York’s East Village is small and so is the audience. Nonetheless, word about “The Rejection Show” is getting around.

The fans come here for the monthly show co-created by Diffee and comedian Jon Friedman a year ago.

Diffee shows slides of his rejected New Yorker cartoons. Writers describe their Top 10 Lists that never made it on the “Late Show With David Letterman.” “Saturday Night Live” skit writers act out the skits that won’t make the show.

“Sometimes the show is terrible, sometimes it’s good,” Diffee says. Most important, he says: “It’s redeeming.”

On this particular week, Mankoff does not buy any of the 10 cartoons Diffee has submitted. Rejections don’t come with explanations. It happens. It’s part of success.