Caddyshack: The Making of a Hollywood Cinderella Story

Caddyshack: The Making of a Hollywood Cinderella Story

by Chris Nashawaty


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“More fun to read than the movie was to watch… a scene-stealing book.”

— The Washington Post

An Entertainment Weekly "Must List" selection

Caddyshack is one of the most beloved comedies of all time, a classic snobs vs. slobs story of working class kids and the white collar buffoons that make them haul their golf bags in the hot summer sun. It has sex, drugs and one very memorable candy bar, but the movie we all know and love didn’t start out that way, and everyone who made it certainly didn’t have the word “classic” in mind as the cameras were rolling.

In Caddyshack:The Making of a Hollywood Cinderella Story film critic for Entertainment Weekly Chris Nashawaty goes behind the scenes of the iconic film, chronicling the rise of comedy’s greatest deranged minds as they form The National Lampoon, turn the entertainment industry on its head, and ultimately blow up both a golf course and popular culture as we know it. Caddyshack is at once an eye-opening narrative about one of the most interesting, surreal, and dramatic film productions there’s ever been, and a rich portrait of the biggest, and most revolutionary names in Hollywood. So, it’s got that going for it…which is nice.

Product Details

ISBN-13: 9781250105950
Publisher: Flatiron Books
Publication date: 04/24/2018
Pages: 304
Sales rank: 467,316
Product dimensions: 5.30(w) x 8.20(h) x 1.50(d)

About the Author

Chris Nashawaty is the lead film critic at Entertainment Weekly, who over his 20 years at the magazine has become one of America’s foremost movie writers and pop-culture authorities. He has appeared on CNN, NPR, Today, and Good Morning America, as well as regularly contributing to Sirius XM’s EW Radio channel. He has also written for Wired, Sports Illustrated, Esquire, Fortune, and Grantland. He is the author of the book about B Movie producer Roger Corman called Crab Monsters, Teenage Cavemen, and Candy Stripe Nurses, and Caddyshack: The Making of a Hollywood Cinderella Story.

Read an Excerpt


The Algonquin Round Table with a Couple of Wobbly Legs

THEY CAME FROM THE COUNTRY'S finest families and belonged to its most exclusive clubs. Yet in 1966, it was exceedingly difficult for a member of The Harvard Lampoon to get laid. It wasn't just because of their withering sarcasm, bookish awkwardness, and fumbling, pre–sexual revolution anxiety (although that certainly didn't help). It was also because the place where they spent most of their waking hours didn't allow women.

Built in 1909 thanks to the deep pockets of William Randolph Hearst, The Castle is a three-story, medieval-looking tower with leaded-glass windows and fortress-grade wooden doors smack in the middle of Bow Street in Cambridge. Perched atop its domed roof is the figure of an ibis — an ancient Egyptian bird that doubles as the Lampoon's cryptic mascot. In the light of day, the strange building looks like a cross between a squat, brick lighthouse and some half-mad architect's idea of a practical joke. The Lampoon's history, however, goes back even further than Hearst's East Coast Castle. Established in 1876, The Harvard Lampoon is the country's oldest college humor magazine, with a roster of famous alumni that includes such urbane wits as Robert Benchley, George Plimpton, and John Updike.

The Lampoon's headquarters had always been an insular place, a sort of patrician social club of high IQ gentleman smart-asses biding their time before they graduated and headed off to Wall Street or to join the family law firm. The summer of 1966 was no different. As antiwar demonstrations broke out on college campuses across the country, the undergraduate rascals inside The Castle were more likely to thumb their noses at the patchouli-scented protesters outside than march alongside them. When not occasionally putting out a magazine, they held to the hermetic, tribal traditions of the past: secret weekly black-tie dinners, Caligulan feats of alcohol consumption, and the fine art of delivering a perfectly crafted cutting remark — an intellectual one-upmanship that bordered on a blood sport. Catching a glimpse of a willing woman in the nude, however, was not one of these extracurricular activities. For that, one had to buy a copy of Playboy.

By the mid-'60s, Hugh Hefner's glossy men's lifestyle monthly was nearing the peak of its popularity, with 6 million subscribers. There were Playboy Clubs from Los Angeles to London and Miami to Manila, all operating on the swinging CEO's pipe-and-silk-pajamas "Playboy Philosophy." If the members of The Harvard Lampoon didn't possess the savoir faire to embody that hedonistic worldview, why not do the next best thing — the thing that they did better than anyone else: make fun of it?

The Lampoon had a long tradition of shooting satirical spitballs at stuffy, mainstream publications. It was like Mad magazine with elbow patches instead of Yiddish puns. But by the '60s, their one-off parodies were still pretty parochial affairs — essentially private jokes told within the seven-square-mile echo chamber of Cambridge. Now, with a target as big and buxom as Playboy, ambitions were scaled up. What if they put out a professional-looking publication to be sold on newsstands from coast to coast? Walker Lewis, who was then the president of the Lampoon, and Rob Hoffman, the son of a well-to-do Dallas family with a mind for business as precise as a Swiss watch, approached Playboy gauging how receptive it might be to some good-natured ribbing. They fully expected the answer to be: Not very. Either that or: Go to hell. As they predicted, The Bunny threatened swift legal action. Lewis fired back, saying they looked forward to all of the free publicity that a lawsuit would bring. Not long after, the phone rang inside The Castle. Hugh Hefner was on the line.

After giving it some thought, Hefner had recognized the value of free publicity on his end, too. Not to mention the priceless measure of Ivy League literary respectability a Lampoon parody might bring. He not only gave his blessing; he offered to whip out his checkbook and help finance it. Hoffman's Dallas connections had already agreed to underwrite the printing bill, but they did take Hef up on the offer of using his distributor. An unprecedented and wildly optimistic 500,000 copies of the Lampoon's Playboy parody (featuring a Little Orphan Bosom comic, a photo of Henry Kissinger splayed out on a bearskin rug in a thong, and a pinup model in a slightly scanty jester's costume on the cover) landed on newsstands on Labor Day weekend in 1966. It sold out in a week.

Henry Beard, one of the issue's key contributors, who, along with Doug Kenney, was also one of the Lampoon's rising young stars at the time, recalls walking with Hoffman to a bank in Harvard Square with a check for $155,000 to be deposited into the Lampoon account. "The whole way we kept saying, 'What happened here? This could be the start of something!' It opened our eyes to the possibility of doing a national humor magazine."

* * *

After the Playboy parody, three things quickly happened at The Harvard Lampoon. The Castle, which had fallen into utter disrepair, got sorely needed updates to its wheezy heating and electrical systems that had basically been left untouched from the days of the Depression. Second, its subscriber base finally spread beyond mere Harvard alumni to a national audience. And third, Beard and Kenney were anointed as the magazine's resident enfants terribles. The whip-smart yin-and-yang hopes for the next generation. They couldn't have been more different.

Henry Beard (class of '67) was, in fact, the genuine WASP article. The great-grandson of James Buchanan's vice president, John C. Breckinridge, he grew up in the Westbury Hotel on the Upper East Side of Manhattan. His father was a Yale-educated Wall Street accountant who was the heir to a family woolen mill in Canada. Before enrolling at Harvard, he attended the prestigious Taft School, where he gave the impression of being a middle-aged curmudgeon while still in his teens. He looked like an exotic baby bird in horn-rimmed glasses, baggy Brooks Brothers tweed blazers, and a pipe clenched between his teeth. There wasn't a lick of irony in the pose.

Doug Kenney (class of '68) had a decidedly different background. He grew up in the improbably named Cleveland suburb of Chagrin Falls, Ohio, where his Irish-Catholic father was a tennis pro. Or, at least, that's how Kenney chose to tell it. In truth, his father had long given up a career of stringing rackets and taken a position as a corporate personnel manager. But his murky blue-collar background made for vivid self-mythologizing. Either way, Kenney had spent his high-school summers working at private clubs, a middle-class kid waiting on blue-blood members not unlike the Beards. Despite Kenney's brilliance, his father had deeply preferred Doug's older brother Daniel — a beloved all-American type who would pass away from kidney failure in his twenties. Doug worshiped him and felt as though his parents saw him as a pale consolation prize — that he should have been the one to die rather than Daniel. At school and at home, he felt like an unloved misfit.

If Beard was a model of wry, cerebral preppy sobriety, Kenney was a hard-to-pin-down wild card, enthralled by the carnal libertinism of the Summer of Love and the dope smoking that came with it. When he entered Harvard in 1964, grass was a taboo recreation punishable by a steep jail sentence. Just a few years later, you couldn't walk down Massachusetts Avenue without getting a contact high. Plus, marijuana seemed to calm Kenney's manic, ever-pinwheeling mind. He could expound on eighteenth-century English literature one minute and astound you with his signature party trick of sticking his entire fist in his mouth the next. While Kenney could inhabit the role of the Gatsby-esque swell as if it were his birthright, he was a chameleon — fair-haired, hysterically funny, and a genius ... but a troubled one.

Flush with the success of its Playboy send-up, the Lampoon briefly flirted with the idea of moving full-time into the parody business. Their follow-up was a riff on Life magazine, Henry Luce's photo-heavy standard-bearer of square, Middle American vanilla complacency. If Hefner's centerfold bible was a buzzed-about cultural lightning rod, Life was the polar opposite. It was so staid and past its prime, it gave off the scent of mothballs. It was a magazine no one much cared about anymore. Parodying it was like picking on the most invisible schoolyard kid at recess.

It didn't help that the country wasn't exactly in the mood for levity. By the fall of 1968, when the Lampoon's "End of the World" Life parody issue appeared, Martin Luther King and Bobby Kennedy had been gunned down; the street-hassle beatings at the Democratic National Convention in Chicago had exposed the toxic rot of the Silent Majority, which was now speaking quite loudly with police batons; and the Black Panthers had taken up arms in Oakland. Then there was the election of Richard Milhous Nixon. It truly did feel like the end of the world. The Life parody would only sell half of its newsstand run, losing nearly $75,000 and sinking The Castle back into the red. But one good thing lay at the bottom of the Lampoon's fiscal sinkhole: Beard and Kenney had been introduced to Matty Simmons.

Simmons was an old-school, cigar-chomping Brooklyn self-promoter with brash gambler's instincts, an outsize, heliocentric sense of himself, and a Barnum-esque flair for hype. It was hard to imagine someone less Ivy League. He'd been part owner of the woeful Philadelphia Warriors basketball team, had once purchased a stable of harness-race horses, and had made a small fortune in stock with Diners Club, the world's first credit card giant, where he published the company's vanity magazine with a partner named Leonard Mogel. When Simmons and Mogel left Diners Club in 1967 and sold their interest, they used the windfall to launch Twenty First Century Communications, a start-up publishing company that, in short order, failed to get a psychedelic magazine called Cheetah off the ground and eventually found a steady money maker (albeit not a very sexy one) in Weight Watchers Magazine. Simmons was hungry to expand what he was bold enough to call his empire.

In the summer of 1968, as Kenney and Beard were putting together their Life parody, and Rob Hoffman was hustling up and down Madison Avenue trying to gin up advertisers, Simmons got a call from Harold Chamberlain, a mutual publishing-industry acquaintance, asking if he would help out these three Harvard students on the business end of their latest venture. Simmons was in the middle of his weekly poker game at his apartment at Park Avenue and 83rd Street. Wanting to keep the conversation short and return to what he thought was a winning hand, Simmons agreed to meet "the boys."

"I was enormously impressed by them," says Simmons. "Rob Hoffman was the business man of the group and did most of the talking. Henry was from a family of millionaires. He was a genius, but quiet. And Doug ... Doug was harder to peg. He was outgoing and handsome and charming, but I don't think I ever thought that he would end up becoming the foremost humorist of his generation."

It was a little late in the game for Simmons to be of much help with the Life parody. By that point, costs had already spiraled out of control and it was more or less doomed. But he was intrigued, and maybe a little dazzled, by these kids who were young enough to be his sons. The idea of teaming up to start a national humor magazine came up, but it was quickly tabled. After all, Kenney and Beard had bigger concerns weighing on their minds.

Like a lot of college students at the tail end of the '60s, they were terrified of the draft. Kenney and Beard had enrolled in ROTC at Harvard (figuring it was better to wind up in the Army Reserves than be shipped off to the front lines). But not surprisingly, both wound up getting kicked out. In Beard's case, the expulsion was for failing to attend the military ball and giving a poorly received lecture on why the US could not win the war in Vietnam. They both had to figure out quickly how to avoid being called up. Beard admits that he might have slid a small amount of money to an officer to regain a place in the Reserves, while Kenney hatched a more devious scheme.

Having heard rumors that the one disqualifying ailment that couldn't be medically diagnosed was epilepsy, Kenney began studying the Merck Manual, memorizing the medical reference book's laundry list of disorders and symptoms. He would become the most convincing non-epileptic epileptic the Army had ever seen. He visited a shady Boston doctor to get a prescription for Dilantin, an anti-seizure medication that he ingested with the commitment of a Method actor. He sat Beard down in the ratty postgraduate apartment they were sharing in Cambridge and briefed him on all of the telltale manifestations of his "condition" (foaming at the mouth, eyes going sideways). Kenney gave Beard's name as a reference to the draft board in case it needed a witness to back up his phony ailment.

In the end, it was moot. It turned out that Kenney's eyesight was so poor that he never would have been drafted in the first place. He was 4-F before he ever popped his first Dilantin. "He went through this whole charade for nothing," says Beard, who graduated a year ahead of Kenney. Both men felt as if they had dodged a bullet. And Beard felt doubly lucky having just been rejected by Harvard Law School, where he didn't want to go in the first place. With their undergraduate years behind them, the question became: What were they going to do now? They couldn't just hang around the Lampoon forever. Or could they?

By 1969, J.R.R. Tolkien's The Lord of the Rings had become mandatory reading for enlightenment-seeking college students between midterms and bong hits. An unlikely cult sensation written by an aging Oxford professor of medieval literature, the patience-testing saga set in Middle Earth was so self-serious and steeped in arcane furry-footed mythology that it was an obvious target to deflate. Kenney, a pop-culture savant with an occasionally cruel gift for mocking the things his peers felt most passionate about, quickly recognized that it would be their next victim. To him, Tolkien's book was the height of flaky stoner stupidity, its popularity utterly dumbfounding. Their title was as dead-on as it was pithy: Bored of the Rings.

Having already proved their financial and creative value to the Lampoon, Kenney and Beard were given small stipends to live on by the magazine after graduating. Their job was basically to brainstorm new parodies that might turn into the next Lampoon golden goose. In addition to their Tolkien takedown, they moved forward with a parody of the venerable Time magazine with Simmons and Mogel on board as partners. Bored of the Rings and Time came out within a week of one another, and both became huge hits. With a shamelessly commercial cover of a half-naked blonde underneath the heavy-breathing line "Does SEX Sell Magazines?," the Time one-off quickly earned $250,000 for The Harvard Lampoon. Its racy cover provided a lesson Kenney and Beard would tuck away for future use. The profits from Bored of the Rings, however, were of a totally different magnitude.

At Hoffman's suggestion, Kenney and Beard had penned a fawning fan-boy letter to Tolkien careful to namedrop some of the Lampoon's more hallowed alumni, essentially asking for his blessing. The subtext of the letter, of course, was that if they got that blessing, it would protect them from whatever copyright issues popped up from Tolkien's litigious publisher. To their surprise, Tolkien wrote back, saying that he had no idea why anyone would want to parody his book, but by all means, have at it and God bless.

"We sat across from each other at a double desk at the Harvard library, and each of us had a portable typewriter facing one another," says Beard. "Doug would type 1,000 words just like that. I've never seen anything like it. He could make 2 plus 2 equal not 4, but 22. He basically wrote that book. It was staggering. I think we wrote the whole thing in four or five weeks. We just clicked."

Beard recalls that when he and Kenney went to New York to deliver the manuscript to their publisher, "It was like he wanted to pick it up with fireplace tongs. He didn't even want to hold it, he thought the idea was so horrible." In their slim, pun-packed paperback, for example, Bilbo Baggins is named Dildo Bugger. Thirty-two editions later, Bored of the Rings has sold 750,000 copies and has been translated into more than ten languages.


Excerpted from "Caddyshack"
by .
Copyright © 2018 Chris Nashawaty.
Excerpted by permission of Flatiron Books.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents

Prologue 1

1 The Algonquin Round Table with a Couple of Wobbly Legs 11

2 If You Don't Buy this Magazine … 31

3 Live from New York 49

4 Knowledge is Good 75

5 Tinseltown Gold Rush 93

6 Like the Dick Van Dyke Show 109

7 Finally, Some Respect 127

8 Rolling Hills … and Action! 145

9 Rappin' Rodney 155

10 The Pizza Man 169

11 Total Consciousness 177

12 Pool or the Pond 197

13 The Dynamite Caper 207

14 The Unkindest Cut 213

15 Enter the Gopher 223

16 Judgment Day 235

17 Welcome, Kenney Mourners! 251

Epilogue 255

Acknowledgments 259

Notes 265

Bibliography 293

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