In the 1972 hit The Heartbreak Kid, screenwriter Neil Simon took the ethnic and class differences hinted at in Bruce Jay Friedman’s short story “A Change of Plan” and made them explicit. New Yorker Lenny Cantrow (Charles Grodin), a sporting-goods salesman, marries Lila (Jeannie Berlin) in a ceremony where a wineglass gets crushed and “(They Long to Be) Close to You” segues into “Hava Nagila.” Lila has a Noo Yawk accent, dark hair, and a certain voluptuousness; the critic Pauline Kael described her as “a middle-class Jewish peasant, her ripe lusciousness a cartoon of sensuality.” (That Berlin is the daughter of the film’s director, Elaine May, suggests the caricature was affectionate.) Down in Miami on his honeymoon, Lenny meets Kelly, a fair-haired, blue-eyed dream girl (played with haughty refinement by Cybill Shepherd), who appears before him on a beach in a halo of sunlight. Lenny soon disposes of his bride and shows up, post-divorce, at Kelly’s Minnesota college; she’s surrounded by hulking football players who fit into Friedman’s genus of “strange blond people with great Scandinavian profiles.” Her dad (a Brylcreemed Eddie Albert) calls Lenny a “New York wiseguy” and tries to buy him off, but soon caves in and lets him marry her. In a church.

In The New York Times, Vincent Canby called The Heartbreak Kid “a first-class American comedy, as startling in its way as was The Graduate.” He also noted that it “begins as a rather familiar New York Jewish comedy,” which tells you something about Hollywood movies of that era. It was a time when Woody Allen’s filmmaking career was taking off (thanks mostly to Canby, Allen’s most prominent cheerleader), Simon’s plays (such as The Odd Couple) were being made into hit movies, and obviously ethnic actors like Elliott Gould, Dustin Hoffman, and George Segal were getting cast in lead roles in M*A*S*H, Midnight Cowboy, and The Owl and the Pussycat.

In Peter and Bobby Farrelly’s remake of The Heartbreak Kid, opening Friday, the only Jewish thing about Cantrow—now a San Franciscan named Eddie—is the person playing him: Ben Stiller, whom the critic David Denby once called “the latest, and crudest, version of the urban Jewish male on the make.” The Farrelly brothers—known for There’s Something About Mary (which also starred Stiller) and other comedies combining outrageous vulgarity with winning sentimentality—upend the original’s assimilationist theme, making Lila

Ben Stiller and Malin Ackerman

(Malin Ackerman), Eddie’s bride, the seemingly perfect blond goddess. On his honeymoon in Mexico the dream girl Eddie meets is Miranda (Michelle Monaghan), a witty, down-to-earth brunette from Mississippi. Yet there’s nothing “Southern” about her; as Eddie points out, she doesn’t even have an accent. The Farrellys are notorious for exploiting and then subverting all kinds of stereotypes—fat people, disabled people, the mentally ill, the Amish—and here the targets are gays, Mexicans, and accented Southerners. (Eddie refers to Miranda’s extended family as “good rednecks, like Jimmy Carter.”) But they leave the Jews alone. While the plot takes Eddie into completely new places (including a bizarre illegal-immigrant third-act interlude), the new ending—a dark punch line—is actually truer to the spirit of Friedman’s story.

The first movie was a sharp-edged satire in which Cantrow had to face the melancholy consequences of attaining his shiksa trophy; the new one is a raunchy romp that mocks the fantasy of true love even as it hinges on it. Once you’ve added a sex-crazed bride and a poisonous jellyfish whose sting requires urine as an antidote, who needs subtext?

In 1964 Melville Shavelson set out to make a Hollywood epic about an American military man who helped establish the state of Israel. Though Cast a Giant Shadow had a generous budget, the full cooperation of the Israeli government, and a star-studded cast including Kirk Douglas, John Wayne, Frank Sinatra, Yul Brynner, Angie Dickinson, and Senta Berger, it flopped. But something great came out of it: Shavelson’s hilarious, groundbreaking 1971 book about the experience, How to Make a Jewish Movie. That his friends suggested a better title would have been “How Not to Make a Jewish Movie” gives a hint of what to expect.

By the 1960s Shavelson was well-known in Hollywood as a maker of comedies. He’d received Oscar nominations for co-writing two films he also directed: the Cary Grant-Sophia Loren romance Houseboat and the Bob Hope vehicle The Seven Little Foys. His association with Hope was his entry into the entertainment biz: Shavelson began writing for him in 1938, and didn’t quit for 20 years. How to Make a Jewish Movie reads like the work of an expert comedy writer. Practically every paragraph ends with a punch line; nearly every sentence has an ironic kick. Shavelson is talented enough to make the story of creating a flop irresistible, and humble enough to accept at least some of the blame. And while the pleasure of How to Make a Jewish Movie comes from the funny stories of difficult actors and shattered $40,000 camera lenses, the book is also a milestone: quite possibly the first book by a Hollywood director devoted entirely to the making of his own movie. Lillian Ross’s Picture and John Gregory Dunne’s The Studio had already given readers vivid behind-the-scenes accounts of Hollywood filmmaking, but Shavelson pulled the curtain back firsthand and revealed, humorously and memorably, the industry’s machinations, long before the public became well-versed in box office figures and books like You’ll Never Eat Lunch in This Town Again shot up the best-seller list.

How to Make a Jewish Movie is primarily a chronicle of everything that can go wrong in the creation of a big-budget film, from rights acquisition to the ad campaign. But Shavelson, who was born in Brooklyn, opens with a confession: “I have never entered a synagogue of my own free will, except for the ceremonies attendant on birth, death, or marriage.”

So how does a comedy writer—especially one who says he was “ashamed” of being Jewish—wind up making an earnest biopic about the founding of Israel? At the suggestion of a friend at MGM, he reads Ted Berkman’s book Cast a Giant Shadow: The Story of Mickey Marcus, Who Died to Save Jerusalem (MGM had just dropped its option on the book, so his friend called to say it was up for grabs), and something is awakened in him:

After reading Ted Berkman’s book I knew I had to make that movie if it killed me. . . . I literally ran to Paramount’s front office and pantingly laid this hot project on the desk of the head man. Would Paramount buy it for me? 

He was kindly, intelligent, shrewd, and went to Temple regularly every Rosh Hashonah. Who, he asked me, would want to see a picture about a Jewish general?

Since, at the moment—and ever since—I couldn’t think of an answer, I decided to buy the rights to the book myself.

The story of David “Mickey” Marcus is indeed awe-inspiring. He was a Brooklyn-born West Point graduate who served as an infantry lieutenant in the ’20s, then returned to New York City to become a gangbusting U.S. attorney and Commissioner of Correction. At the outbreak of World War II he rejoined the army. According to Shavelson’s screen treatment (which he prints in full in the book) Marcus wrote Army training manuals, made his first parachute jump into Normandy on D-Day, drafted the terms of surrender for Italy and Germany, and “was at Roosevelt’s side at Cairo, Teheran, Quebec, and Yalta.” In Germany, General Patton appointed him liaison officer with liberated concentration camp survivors. He was made second-in-command in occupied Berlin, and organized the Nuremberg trials and Japanese war crimes trials. In 1947, having returned to New York to work as a lawyer, Marcus was quietly asked to guide the untrained and ill-equipped Jewish troops of Palestine in their fight for independence. He did it under an assumed name, with the secret blessing of the Pentagon. Against all odds he led Israel’s army to victory upon the nation’s birth—and was mistakenly killed by an Israeli sentry just a few hours before a truce was declared.

Shavelson’s own story of putting together Cast a Giant Shadow is heroic, too, in its way: he’s a mensch in the face of disaster. He makes the film sound like the most troubled shoot since Cleopatra, but does it in an avuncular, anecdotal way that anticipates Sidney Lumet’s 1995 book, Making Movies. Needing the involvement of a star—preferably a non-Jewish one—to make his project viable, whom does Shavelson go to first? The least Jewish man in Hollywood, John Wayne. Shavelson had co-written a movie for Wayne in the past, but they had squabbled on the set. Undeterred, he pitches Marcus’s story, ending by reading a eulogistic telegram to Marcus’s widow from David Ben Gurion. Wayne (known to all as Duke) lights a cigarette and says:

“That’s the most American story I ever heard.” 

I wasn’t sure I understood him correctly. Ben Gurion had signed that telegram—not Ben Franklin.

“Everybody’s knockin’ the United States today,” Duke said, pacing the floor and covering half an acre of carpet with each stride. “Claiming we’re sendin’ in troops all over the world to knock over some little country where we’ve got no right to be. They’ve forgotten who were are and what we’ve done. At a time like this, we need to remind them of how we helped the littlest country of all get its independence. How an American army officer gave his life to do it.”

“Mickey was Jewish,” I insisted on reminding him.

“Don’t gimme that crap,” said Duke, “Jesus Christ was Jewish, too, and he didn’t even go to West Point.”

So, in a gesture of grand patriotism, Wayne agreed to appear in the picture. Not as Marcus—that role would go to Douglas, an actual Jew—but as a Patton-like general whom Shavelson would insert into his as-yet-unwritten script. Shavelson then took his pitch to the Mirisch brothers, Harold, Walter, and Marvin, “collectively the world’s largest independent producer of films,” and a deal was made. Soon after, in a location scouting trip to Israel, Shavelson got an early warning of the difficulties to come: The army’s commander-in-chief—none other than Yitzhak Rabin—demanded script approval. And, “in the event that the script should be approved, he went on to say, all film shot in Israel would have to be reviewed by the military authorities before being shipped out of the country.”

Luther Adler and Kirk Douglas in Cast a Giant Shadow

In 1965 filming got under way in Tel Aviv with 125 crew members, 800 Israeli soldiers, and a thousand extras. The problems began immediately: During a shot, Israeli tanks left abruptly when the army learned that Syria had invaded; nearly all the trucks in another shot stalled when the desert temperature hit 126 degrees; the two technical advisors provided by the army clashed over key details; Israel’s Communist Party dropped leaflets from a roof into the middle of a crowd scene. Along the way, Brynner went unrecognized by Ben Gurion (“The King and I. . . which one were you?”), and Shavelson and Douglas bickered repeatedly over the script. On the last day of filming in Israel, 200 extras shot half of a scene, disappeared while the next shot was set up, and sent in a representative to proclaim that they had united as the Israel Screen Extras Guild and would not return until their salaries were tripled. After examining the footage, the Israeli Defense Forces sent a detailed critique, which included: “In Scene 327, the girl with a flowery skirt doing the Hora is completely out of step. Change this.”

When Cast a Giant Shadow was released in 1966 the question “Who would want to see a picture about a Jewish general?” loomed over the national advertising campaign, which lacked, Shavelson writes, “all mention of the nation of Israel, the War of Liberation, the Jews, or Colonel Mickey Marcus.” Relating this fact, he seems understandably peeved. What he doesn’t say (perhaps it was a sore point) is that Otto Preminger’s Exodus, which also concerned the founding of Israel, was the fourth-biggest box-office draw of 1960. Cast a Giant Shadow didn’t earn back the cost of its negative.

So, how’s the movie? Kitschy. Its dialogue sounds, not coincidentally, like the work of a comedy writer. When Marcus tells Ben Gurion (played by Luther Adler, in a ridiculous white wig that makes him look more like Martin Van Buren) that Jerusalem has no strategic value, and that trying to save it doesn’t make sense, Ben Gurion says, “Did it make sense for a fellow with a nice, steady job building pyramids to march his friends into the Red Sea?” When it’s serious, it’s worse. A didactic argument between Marcus and Wayne’s American general about Israel’s future ends with Wayne—John Wayne!—raising his glass and declaring, “L’chaim.” (He pronounces it “la kime.”) Sinatra is amusing as a New Jersey pilot who drops seltzer bottles on the Arabs when the Israelis run out of bombs. Douglas is suitably rugged, and Brynner pontificates impressively. But Shavelson himself calls it “a not-very-good movie.” Pauline Kael’s assessment was more blunt: “Even those willing to accept the hours of incoherence and banality may recoil at the obscenity of being asked to experience the horrors of Dachau as reflected in John Wayne’s bleary eyes.”

In his 1988 autobiography, The Ragman’s Son, Kirk Douglas still sounds disappointed when he writes of Shavelson: “Though Mel was Jewish, he was not Jewish enough. The movie needed to be done by someone with deep conviction.” If he didn’t have conviction when he started the picture, Shavelson says he did by the end. Like his film’s protagonist, he comes to find Israel’s stubborn citizens exasperating but admirable, and his months among them turn him into something of a Zionist. Halfway through the book, at a seder, he has an epiphany: “The escape had taken place, not in some mythical land with an impossible alphabet no one could ever learn, but only a few miles from here, across the desert where tanks had recently rumbled out of that same land of Egypt, only to be turned back in defeat by the descendants of those who had written the very songs the children were singing.” He’s finally proud to be Jewish, proud to have made a movie about Jewish pride. The fun of the best making-of movie books, such as Final Cut (about Heaven’s Gate) and The Devil’s Candy (about The Bonfire of the Vanities), often comes from schadenfreude—the pleasure of witnessing the payback for megalomania and excess. But you feel for Shavelson, because his intentions are so pure, and because he seems like such a nice guy. He also seems to have learned, as an entertainer, that the story of a nice Jewish filmmaker who finds himself while shooting a $5 million flop has more potential in the hands of a comedy writer than the story of a Jewish general who gets killed.

Shavelson continued making movies into the 1970s—comedies, mostly. In 1990, more than 50 years after he began writing for Bob Hope, they wrote a bestselling book together, Don’t Shoot, It’s Only Me. Now 90, Shavelson is finishing up a memoir, which he’s calling How to Succeed in Hollywood Without Really Trying—P.S., You Can’t. Asked over email about How to Make a Jewish Movie, he pooh-poohed the idea of it being a literary milestone: “I wrote it in part to counter all the negative reviews the film inspired, and to show how a bad film can be explained by circumstances, as well as lack of talent….My old friend Julius Epstein, co-writer of Casablanca, always said the Academy should stop restoring old negatives and start destroying a few. Cast A Giant Shadow might be a candidate.”

Cast a Giant Shadow is available on DVD. How to Make a Jewish Movie is long out of print.