Josh Shaffer

Shaffer: Raleigh lawyer a finalist in New Yorker caption contest – twice

Press Millen, an attorney representing a group opposing the Voter ID law, makes his case at a hearing on Jan. 30.
Press Millen, an attorney representing a group opposing the Voter ID law, makes his case at a hearing on Jan. 30. cseward@newsobserver.com

When they’re not eye-deep in law books or dissecting squid, brainy eccentrics enjoy unwinding with their own brand of competitive sport: finishing the Saturday crossword in the New York Times, winning the NPR news quiz on “Wait, Wait, Don’t Tell Me.”

But the Everest of egghead challenges arrives weekly on the back page of the New Yorker, the cartoon caption contest in which 5,000 smart cookies try to write the drollest joke.

Somewhere in the neighborhood of 5,000 highbrow competitors send in their most obscure references, their most offbeat gags, hoping to see their names in the New Yorker’s august pages. Many of these contestants, I feel certain, would trade their 20-volume set of the Oxford English Dictionary for a win.

So consider this achievement:

Press Millen, trial attorney with Womble Carlyle, has out-quipped his rivals and been named a caption contest finalist for the second time in one year. News of whether his latest opus wins the whole shebang could arrive as early as today.

So I buttonholed Millen in court on Friday, where he was arguing against the state’s voter ID requirement, and asked him to define the perfect New Yorker joke. Not side-splitting. Not guffaw-inducing. More of a chin-scratcher with a half-smile.

“Maybe ‘wry’ would be a good word,” he said.

The magazine won’t let me reprint the cartoon, so I’ll direct you to the Jan. 26 issue to view Millen’s esteemed gag.

It’s a classic New Yorker setup: an executive type is sitting behind a desk in a big downtown office, skyscrapers visible out his floor-to-ceiling windows, where he’s conducting what appears to be a job interview with a sphinx.

The three finalist captions:

“So, where do you see yourself in five thousand years?”

“How long have you been in your current position?”

And Millen’s, the clear winner to my mind: “I may have something for you in Vegas.”

Millen fleshed out his thinking, which captures the essence of a New Yorker cartoon. You’ve got to avoid all the obvious references. Don’t say Egypt. Don’t say King Tut. Pick something totally incongruous for the punch line.

“On the one hand it’s a disparate concept,” Millen said, explaining his Vegas reference. “On the other hand, they have a hotel there that’s got all this Egyptian crap on it.”

Millen resolved to be a serious contest entrant at the beginning of 2014. Since then, he’s taken this approach: Sit down and write 10 captions for each cartoon, scribbling them in the margins, then pass them around to an informal group of judges made up of friends, family and co-workers. He rarely gets any consensus, but the feedback helps him select the best candidate.

It’s a nice diversion for a lawyer who specializes in antitrust cases, unfair trade practices and trade secrets. He gestured to the jumble of legal pads spread across the courtroom desks. “Do you see any levity in here?”

I only got a few minutes to pick Millen’s brain. Great caption writers, much like exotic birds, rarely give their admirers much of a glimpse. Before we could get into a serious New Yorker confab – What’d you think of the Jeb Bush profile? Hasn’t it been a while since Shouts & Murmurs was funny? – Millen dashed back to work.

“I’m immersed in the 1868 constitution,” he explained.

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