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Neil Simon’s humor made him endearing; his warmth made him enduring.

Neil Simon, who died this Sunday, August 27, at age 91, was arguably the most successful playwright in American history, an icon whose works captured the zeitgeist of American middle-class life for much of the 20th century.

One of only three playwrights whose name graces a Broadway theater (along with August Wilson and Eugene O’Neill), Simon was known for his long-running stage comedies, many of which were hysterically funny even as they drew on real cultural anxieties and states of modern life. The most famous of these is The Odd Couple, the smash theater hit that became an even bigger movie.

But Odd Couple was by no means the first, or anywhere near the last, of Simon’s huge hits. As Frank Rich, the longtime New York Times theater critic, wrote about Simon in a memorial for Vulture,

It is probably impossible for those theatergoers who didn’t grow up with Neil Simon’s plays to understand how big a deal he was in his prime, both to the theater and American pop culture. … For a while it was all Neil Simon all the time — remarkably so given that his mainstream branch of domestic comedy was in conflict with a culture, in theater and movies alike, that was moving fast in the opposite direction.

Simon was a four-time Oscar nominee and a staggering 17-time Tony nominee; he won three times and received a special Tony in 1975, along with virtually every other honor a playwright can win, including the Pulitzer Prize for 1991’s Lost in Yonkers. Because he was so prolific, churning out more than 60 plays, screenplays, teleplays, and even contributions to musicals over the course of half a century, it’s hard to home in on his most important works, or even his most important decade. But here are four Simon works we think every theater lover should know.

Barefoot in the Park (1963)

The sweetly funny, winsome story of two honeymooners awakening to the harsh reality of newly married life, Barefoot in the Park not only began Simon’s theater box office reign but kicked off his longtime collaboration with director Mike Nichols. Robert Redford starred in this megahit play on Broadway, and then reprised his role alongside Jane Fonda for the 1967 film.

In many ways, Barefoot in the Park is a natural predecessor to The Odd Couple; both stories involve two characters learning to live together and develop a new understanding of each other in various states of pressure. And like Odd Couple, Barefoot imbues its story with a balance of gentle fun-poking and eventual optimism about its outcome.

The Odd Couple (1965)

The Odd Couple is both Simon’s most universally relatable play and his funniest — which is why this story of two single friends who become the world’s most dysfunctional roommates, immortally portrayed onscreen by Walter Matthau and Jack Lemmon, has become a ubiquitous part of pop culture.

Full of iconic moments, from its famous opening poker scene to its hilarious one-liners (“‘We’re all out of cornflakes. F.U.’ Took me three hours to figure out F.U. was Felix Ungar!”), The Odd Couple is a dream play for any pair of actors with chemistry. That’s why it’s been gender-swapped, performed thousands of times, and even expanded into a popular, ambiguously queer ’70s TV series. It’s a fizzy mix of coy wit and slapstick physical comedy that says more than words ever could, as Matthew and Lemmon illustrate below.

Sweet Charity (1966)

It’s hard to overstate what an impact the one-two-three punch of Barefoot, Odd Couple, and the Cy Coleman/Bob Fosse musical Sweet Charity had in the mid-’60s in terms of establishing Neil Simon as the reigning king of Broadway. Each of these productions is full of light and infectious comedy, and all straddle the social strata of 1960s New York.

The story of a dance hall girl making her way in the world through a string of relationships, Sweet Charity is indelibly a Fosse musical — and the film is one of his slickest achievements as a director and choreographer, though at the time it was a major box office flop. But it owes its humor to Simon, who adapted the plot loosely from the Fellini film Nights of Cabiria. And in numbers like the one below, we get a glimpse of Simon’s tongue-in-cheek but ever-present warmth toward his characters:

Lost in Yonkers (1991)

Toward the end of his career, Simon wrote a string of loosely autobiographical plays in which he turned away from the more overtly comedic and began lacing his familiar family dysfunction and portraits of odd bedfellows with real conflict, drama, and even pain. The most successful of these are the three ’80s plays about military life known as the Eugene trilogy. The plays — Brighton Beach Memoirs, Biloxi Blues, and Broadway Bound — feature a recurring character named Eugene, and incidentally made Matthew Broderick, who portrayed him twice on Broadway, into a star.

But it wasn’t until 1991’s Lost in Yonkers, which won Simon the Pulitzer Prize and earned its star Mercedes Ruehl a Tony, that critical opinion began to definitively embrace Simon as a literary playwright as well as a comedian. The story of a free-spirited woman trying to assert herself against her family’s iron-willed matriarch, Simon’s dramedy is a poignant look at a typical dysfunctional American family; but even more, it’s a deeply personal study in Jewish-American identity and culture during World War II, at a moment when the idea of family and community must have felt nearly fragmented and shell-shocked beyond repair.

Check out the trailer for the ’93 film adaptation of the play, directed by Martha Coolidge, below:

And here’s Simon himself discussing why Yonkers is his personal favorite of his plays.

Author: Aja Romano


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