6 storytelling lessons from Neil Simon

The playwright and screenwriter, who died Sunday at 91, was known for family dynamics, comedic gold and tidy storylines. Here are storytelling insights from a storied writing career.

Neil Simon storytelling tips

Few writers have ever soared to such sustained heights as playwright Neil Simon did, beginning with a burst of success in the 1960s.

Simon died Sunday at age 91 in New York, leaving an expansive comedic legacy and a trove of lessons for any writer to emulate.

Simon was a four-time Oscar nominee and a 17-time Tony nominee. At one point in 1966 he had four plays running on Broadway simultaneously and even owned a Broadway playhouse. In 1983, he had a Broadway house named for him.

Yet he long suffered under the label of a commercially popular, yet critically underappreciated writer. Only when he dug into his own personal background with such autobiographical works as “Brighton Beach Memoirs,” “Biloxi Blues” and the Pulitzer Prize-winning “Lost in Yonkers” did Simon capture both popular and critical acclaim.

Communicators have much to learn from the long career Simon enjoyed. Whether it’s employing humor to explore emotional truth or drawing from personal experience to weave a compelling narrative, communicators should remember what Simon knew to be the only hard rule in storytelling: Don’t be boring.

Here are lessons from some of Simon’s most-beloved works:

1. Repurpose old ideas.

Simon wasn’t afraid to recycle, most notably borrowing a structure from his Manahattan-based play “Plaza Suite” for his later “California Suite.”

He also frequently returned to familiar themes, such as a mismatched couple learning to live with each other in “Barefoot in the Park” and “The Odd Couple.” He would later reuse the same character, named Eugene, as a stand-in for himself in his autobiographical works “Brighton Beach Memoirs,” “Biloxi Blues” and “Broadway Bound.”

Communicators can reuse content and retool their work for different social media channels.  Your videos can become fodder for infographics and blog posts, keeping your audience engaged and reaching new segments.

You can also find inspiration in others’ work. Simon tapped the biblical story of Job in penning “God’s Favorite” and the writings of Anton Chekhov for “The Good Doctor.” Read, ponder, explore.

2. Going viral is often about luck.

Despite unmatchable success on Broadway, Simon would also see plenty of failures on the Great White Way. Despite still writing into the new millennium, Simon saw several flops and a revival of his lauded “Brighton Beach Memoirs” close after only a week of performances.

The New York Times reported:

“I’m dumbfounded,” he said. “After all these years, I still don’t get how Broadway works or what to make of our culture.”

It was a poignant comment from the man who more or less defined Broadway achievement for a couple of decades. But while quick flops were relatively rare in his career, Mr. Simon always fought to gain critical respect. Although he was nominated for 17 Tony Awards, he won just three: for author of “The Odd Couple,” and twice for best play, for “Biloxi Blues” and “Lost in Yonkers.”

“I know how the public sees me, because people are always coming up to me and saying, ‘Thanks for the good times,’” Mr. Simon told The Times in 1991. “But all the success has demeaned me in a way. Critically, the thinking seems to be that if you write too many hits, they can’t be that good.”

Even great writers can be subject to the whims of the public sphere—and betting on viral success is a poor way to plan any communication strategy.  Savvy communicators know to celebrate exceptional popularity, but not to take the credit for it.

It’s important, too, for writers of all stripes to develop a thick skin.  Even the most successful wordsmiths get critiqued.

3. It’s helpful to have a few stars.

Simon’s plays made major stars out of several actors , including Robert Redford, Matthew Broderick and Jane Fonda. Jack Lemmon and Walter Matthau would reprise their partnership in Simon’s “The Odd Couple” for movies such as “Grumpy Old Men.”

Today’s communicators shouldn’t discount the power of celebrities and stars in their efforts, either. As influencer marketing and the waxing power of social media continues to drive public conversation and nationwide sentiment, partnerships with popular individuals on any level could be a boon for your PR campaign.

4. Make ’em laugh.

Simon was, above all, funny—part of a class of comedic geniuses that included Woody Allen, Carl Reiner and Mel Brooks. His wide popularity was firmly rooted in his ability to make his audiences ache with laughter.

Communicators should be clever and concise in their writing. Humor has a lot of power on social media. Even drier subjects like health care marketing can contain humorous tidbits. Granted, attempting humor in corporate communications can backfire, so to be sure you are toeing the line, follow these guidelines.

5. Find the extraordinary from the ordinary.

Simon’s work consistently focuses on the ordinary occurrences of life—and how they can become the extraordinary moments that define one’s existence.

Communicators and storytellers can waste precious time looking for outlandish narratives to share with their audiences. There is plenty of drama in the small acts that fill every day.  It just takes a talented writer to see them and exploit their possibilities.

6. See (and tell) your story from multiple angles.

Conflict between equally sympathetic characters draws the audience in. For example, are you an Oscar or a Felix?  In “The Goodbye Girl,” do you side with Paula (Marsha Mason) or Elliot (Richard Dreyfuss)?

Simon invariably injected a serious element into his comedy, as well. Jack Lemmon and Sandy Dennis in “The Out-of-Towners” are pushed to their limits, and viewers, through their laughter, ache for the harried husband and wife with each mishap.

Striking those balances will captivate an audience. The dramatic structure introduces the characters, sets up the premise, incites the conflict and carries everyone on through the resolution—be it comic or poignant. (It’s often both, in Simon’s works.)

Which of “Doc” Simon’s works might provide inspiration for you?

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