How to be sharp and sweet

Or, two lessons from the life of Robert Benchley

Imagine you are a profoundly unhappy man. You cheat on your wife and drink heavily, finding no solace in either vice. You see yourself as a failure, living proof that everyone becomes what they hate the most. By the end of your days, the sleeping pills you take keep you awake, the amphetamines you take put you to sleep, and ultimately you can’t think of any good reason not to be unconscious.

Bummer, huh? But here’s the twist: Imagine you are also known as “one of the world’s warmest wits” and “the most admired humorist of your generation.” Biographies written about you are subtitled Laughter’s Gentle Soul and His Life and Good Times. Not only do you light up every room you enter, but those rooms and their occupants stay lit well after you depart. Everyone loves you. 

Robert Benchley had it both ways, and there’s a good lesson in what he did wrong and a better lesson in what he did right. In short: Know when to stop trying and know when to stop talking.

As an editor of the Harvard Lampoon, founding member of the Algonquin Round Table, and drama critic for The New Yorker and Life magazine in the 1920s and ’30s, Benchley became famous for a special brand of light-hearted nonsense. His columns had titles like “Why Do We Laugh — Or Do We?” and “The Menace of Buttered Toast.” Upon visiting Venice, he sent his editor a telegram reading “STREETS FLOODED. PLEASE ADVISE.”  He shared a co-working space — think WeWork with bathtub gin instead of kombucha — with Dorothy Parker, of which he said “one cubic foot less space and it would have constituted adultery.” He churned out copy, joking that “the biggest obstacle to professional writing is the necessity for changing a typewriter ribbon” — until he worried he would run out of ideas. Then he moved out to Hollywood and became a celebrated comic actor and screenwriter. (You can watch his Oscar-winning 1935 short “How to Sleep” here.)

But succeeding in two competitive, high-profile careers was not enough. Like Parker, he excelled at light verse but longed to write something heavier — specifically, a scholarly history of the Queen Anne era. Benchley once joked that “anyone can do any amount of work, provided it isn’t the work he is supposed to be doing” — and an academic study that proved he could be a serious writer was the work he thought he’d been neglecting. That such an obscure goal should sink him is perhaps the darkest joke of his life. The lesson: Sooner or later, everyone needs to put a cork in their ambition. 

Now for the good news: Robert Benchley’s reputation for gentle wit was less about how he spoke and more about how he listened. “Most people feel there’s a lot more to them than the world ever sees,” wrote Babette Rosmond, his most amusingly named biographer. “Benchley was the man to bring it all out.” He could quip with the best of them, which only made him a better listener. He gave his companions his full attention, and they loved him for it. As his son Nathaniel explained:

“No two people remember him in exactly the same way, and the knack he had for making other people feel humorous now causes many of them, in reminiscing about him, to remember what they said and did, rather than what he said and did.”

Benchley’s contemporary Robert Sherwood said, “So formidable was his reputation as a merry-andrew that we started laughing at the very mention of his name.” How do you unlock that level of achievement? In Nathaniel Benchley’s words, the trick is to cultivate an “unerring knowledge of the precise word or action that would make a person feel at ease, or happy, or important, and it is these things that are remembered by people who couldn’t repeat to you one funny word he ever said.”


Quick quips; lightning

“We cherish our friends not for their ability to amuse us, but for ours to amuse them.” — Evelyn Waugh

Waugh (1903-1966) was reputed to be as cruel as Benchley was kind, but they both understood this essential fact.

A good joke turns life inside out.”— Terry Jones

And most people welcome the change in scenery.

If at first you don’t succeed, try, try again. Then quit. No use being a damn fool about it.” — W.C. Fields

Persistence beats resistance, yes, but sometimes you need distance.


Thanks for reading the thirteenth issue of Get Wit Quick, the weekly Venetian traffic report.  It goes with my book Elements of Wit: Mastering The Art of Being Interesting like butter on toast. Those looking for a witty summary of the Queen Anne era could do worse thanThe Favorite. Those looking for another email roundup of clever odds and ends should try Curio, from which I recently learned about Marchetti’s Constant. Know any fellow merry-andrews who’d appreciate this newsletter? Forward away, friend! And tap the heart below!