Elaine May and Neil Simon craft a biting satire in The Heartbreak Kid, where a shallow Jewish newlywed ditches his wife mid-honeymoon for another woman.

“This is honest food. There is no lying in that beef. There’s no insincerity in those potatoes. There’s no deceit in the cauliflower. This is a totally honest meal.” – Lenny Cantrow in The Heartbreak Kid

It’s not often that one gets the chance to see The Heartbreak Kid, whether in theaters or at home. The film has long been absent from digital retailers and streaming platforms, and any theatrical showing feels more like happenstance than certainty. For me, it was the “white whale” of the AFI 100 Years…100 Laughs list (#91), until I spotted it streaming on Netflix back in September 2010. By then, the DVD was already long out of print, and that brief window turned out to be my last opportunity to watch the film until this past Sunday afternoon.

In New York City, Lenny Cantrow (Charles Grodin), a self-absorbed sporting goods salesman, finds himself trapped in an awkward situation with Lila Kolodny (Jeannie Berlin), a young woman who insists on chastity until marriage. Pressured and impatient, Lenny hastily marries her, only to discover on their Miami honeymoon that the very intimacy he sought leaves him uneasy and disillusioned.

In Miami, Lenny encounters Kelly Corcoran (Cybill Shepherd), a vivacious college student on vacation with her wealthy parents. Smitten, he engages in a series of elaborate schemes to pursue her, deceiving Lila and inserting himself into Kelly’s holiday. His behavior entertains Kelly but infuriates her protective father (Eddie Albert), creating increasingly awkward and comedic tension.

Lenny ultimately divorces Lila and follows Kelly to Minnesota, navigating her father’s distrust and a failed attempt at bribery. Through persistence and charm, he wins over Kelly’s mother, Mrs. Corcoran (Audra Lindley), and finally secures Kelly’s hand after refusing a $25,000 bribe from her father, culminating in a Christian wedding that signals his latest conquest.

Yet at the reception, Lenny’s shallow, self-centered nature resurfaces. Engaging in banal, clichéd conversations with guests and children alike, he drifts into boredom, suggesting that his restless pursuit of excitement may once again undermine his happiness and hinting at the film’s darkly comic critique of romantic impulsiveness.

The Heartbreak Kid earned two Oscar nominations following its release: Jeannie Berlin for Best Supporting Actress and Eddie Albert for Best Supporting Actor. Both are well-deserved. You can’t help but feel for Berlin’s Lila, sunburned on the very first day of her Florida honeymoon and left behind while Lenny’s tuchas has all the fun cheating and lying. He should have been forthright from the start.

Neil Simon adapts Bruce Jay Friedman’s “A Change of Plan” into a script full of sharp, incisive writing, brought vividly to life by the cast—with a healthy dose of improvisation. Elaine May, drawing on her Compass Players and Nichols and May background, has a clear vision for The Heartbreak Kid, likely refining Simon’s screenplay in the process. The film’s laughs aren’t driven by punchlines but by characters caught in painfully awkward situations.

There’s also much to say about Jewish identity in The Heartbreak Kid. With a number of Jewish creatives in front of and behind the camera, it’s inevitable that Jewishness informs the story. Beyond cultural detail, though, Eddie Albert’s Mr. Corcoran carries hints of antisemitism. The script never dwells on it, but offhand remarks surface throughout and Mr. Corcoran has a clear dislike of Lenny, adding another layer of tension to Lenny’s pursuit of Kelly.

May directed The Heartbreak Kid five years after ex-partner Mike Nichols completed The Graduate. The comparisons are obvious—Charles Grodin as a kind of parallel to Dustin Hoffman, Jewish men chasing blonde WASPs—but the films diverge in what they say about assimilation and American affluence. Lenny is a nebbish Jew or schlemiel who “wins” the non-Jewish woman, but in the end he’s still alone, humming the song he once shared with Lila on the way to Miami.

Over half a century later, The Heartbreak Kid still stings with its satire of love and selfishness. With Elaine May’s direction and Neil Simon’s script, the film delivers a comedy that’s funny, uncomfortable, and endlessly rewatchable—a reminder that chasing what we want doesn’t always bring happiness. Now if only the film would be more widely available for audiences to watch on home video!

DIRECTOR: Elaine May
SCREENWRITER: Neil Simon
CAST: Charles Grodin, Cybill Shepherd, Jeannie Berlin, Audra Lindley, and Eddie Albert

20th Century Fox released The Heartbreak Kid in theaters on December 17, 1972. Grade: 4/5

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