Easter in 1988 fell on April 3, a period when American high schools and colleges typically granted students one to two weeks of spring break. Young people formed the core moviegoing audience, making Easter a key release window in North America.
On March 25, as the Easter frame began, When Harry Met Sally—after two weeks of previews—expanded wide on 1,077 screens.
Also opening that day were three films targeting the holiday crowd: Universal's Biloxi Blues, Orion's Johnny Be Good, and Paramount's The Moderns.
Among the new releases, Biloxi Blues starred Matthew Broderick, who had previously clashed with Simon—an arrangement hardly coincidental. Broderick and Michael J. Fox, propelled to fame by Back to the Future, were the era's most popular young male stars among teens. This explained why Fox's The Secret of My Success had also targeted Easter the previous year.
Unlike Broderick's prior two middling efforts, Biloxi Blues earned widespread critical praise. Absent When Harry Met Sally, it would undoubtedly have dominated the holiday.
Now, bolstered by Disney's aggressive promotion, two weeks of strong word-of-mouth from previews, and buzz around Meg Ryan's restaurant scene, When Harry Met Sally far outshone its Easter rivals in both reviews and topical heat.
Moreover, a film destined to remain a beloved classic decades later could scarcely be matched by factory-crafted teen popcorn fare like Biloxi Blues or Johnny Be Good.
Thus, in its wide-opening weekend, When Harry Met Sally galloped to an unchallenged $17.81 million.
By comparison, the runner-up Biloxi Blues fell below $10 million—$9.13 million on 1,239 screens—while Johnny Be Good, The Moderns, and holdovers lagged further behind.
From March 25 to 31, seventeen films in North American theaters grossed a total $60.33 million; When Harry Met Sally alone claimed 29.5 percent, leaving the remaining sixteen to split the rest.
On April 1, when the new weekly figures emerged, many despite mental preparation from the preview phase—wondered if it was an April Fool's prank.
The top five films included When Harry Met Sally with the fewest screens. Warner Bros.' heavily backed Police Academy 5: Assignment Miami Beach played on 1,700 yet earned only $5.09 million in its second week, ranking fifth with a $12.52 million cumulative.
When Harry Met Sally, on 1,077 screens, had already surpassed $20 million in three weeks—including previews—reaching $21.56 million.
During last year's pitch for When Harry Met Sally, virtually every major studio dismissed the project. Even after Simon's string of successes softened attitudes, Daenerys ultimately signed a highly unequal distribution deal with Disney.
Though details remained confidential, in a town with few secrets, the terms became fodder for industry gossip.
Simon's sudden billionaire status from futures trading, followed by months of perceived Hollywood extravagance, had earned him labels like rookie, mark, and nouveau riche.
Since the studio system's consolidation half a century earlier, countless outsiders attempting to carve their own niche had failed. Recent flameouts like Cannon Films, De Laurentiis Entertainment, and New World Entertainment served as stark warnings.
To many, Simon Westeros's recent moves seemed to follow the same doomed path.
Now, with When Harry Met Sally's release, observers began to reassess the young man who had stormed Hollywood less than two years earlier.
A wide opening exceeding $20 million, combined with glowing reviews and massive buzz, made a $100 million North American total highly likely.
Or, dispensing with caution: When Harry Met Sally was poised to become 1988's first domestic century-breaker.
Crossing $100 million domestically—a seemingly simple milestone—was a lifelong dream many Hollywood figures never achieved.
Annually, four to five hundred films reached North American theaters. Over the past decade, an average of fewer than five per year hit the mark—and most benefited from top talent plus studio marketing muscle. Pure dark-horse breakouts were rarer still.
Yet for one young man, the barrier appeared effortless.
Last year's three Simon films: one claimed the annual crown, one cleared nine figures, and even the lowest-grossing Final Destination landed ninth with over $70 million.
In the new year, as many watched with schadenfreude a suddenly rich kid seemingly run amok, a romantic comedy virtually the entire town had dismissed abruptly revealed nine-figure potential.
Four consecutive films, four consecutive triumphs.
Anyone of normal intelligence could no longer dismiss Simon Westerlo's streak as luck.
"…"
"Meg Ryan is gorgeous—and that scene, haha, classic. I'm definitely buying the videotape for my collection."
"…"
"Does Meg Ryan have other films?"
"She played the pilot's wife who dies in Top Gun—remember? But her look there was awful, and the performance over-the-top. No wonder it didn't stick. She's clearly better suited to Sally."
"…"
"Autumn in New York is stunning. Toby, let's visit in the fall—stay at Aunt's."
"…"
...
Inside a Burbank cinema.
As the film ended and departing patrons buzzed with discussion, CAA president Michael Ovitz—still seated—turned to Disney CEO Michael Eisner beside him. "Counting Good Morning, Vietnam, that makes five. Late last year, Simon Westerlo urgently wanted to sign Robin because he spotted that film's potential. I blocked it, causing a minor rift. Now I'm questioning whether I was right—Robin might have missed an even better opportunity."
When Harry Met Sally was Disney-distributed; Eisner could have had a print delivered with one call. Yet both men wanted to gauge audience reaction firsthand, hence the theater visit.
Eisner knew the backstory of Ovitz's sudden interest in Good Morning, Vietnam and the private family screening. Listening to the enthusiastic chatter around them, he asked, "That script, Michael, tell me more?"
"A drama called Dead Poets Society," Ovitz replied. "If you're interested, I'll have a copy sent over."
Eisner nodded, then added abruptly, "Michael, any chance Disney could acquire Daenerys Films?"
"Post-When Harry Met Sally, every major will entertain the thought," Ovitz said with a smiling shake of his head. "But consider the kid's net worth—why would he sell his studio?"
Eisner persisted. "He might want the backing of a major. His filmmaking genius is undeniable, but he's a mess at operations. In his shoes, I never would have signed that original Disney deal."
The Daenerys-Disney contract stipulated: for North American gross up to $40 million, Daenerys paid Disney a flat $6 million distribution fee. Above $40 million, Disney took 18 percent of the excess.
Thus, the higher the gross, the greater Disney's relative fee—an inversion of industry norm.
At a conservative $100 million domestic, Disney would earn $18 million in fees alone, plus priority rights to ancillary channels.
As close friends, Ovitz knew the broad strokes.
Simon's post-wealth Hollywood moves often appeared haphazard.
Yet Ovitz gestured toward the screen. "Michael, without that seemingly disadvantageous contract, would Disney have promoted the film so aggressively?"
Eisner paused, realization dawning, and gave a wry smile. "No. And under standard terms, I certainly wouldn't have granted Easter or over a thousand screens."
Ovitz shrugged. "So do you still think the young man can't run a company? To me, his grasp of Hollywood rivals ours. He also knows when to yield to gain. Look at When Harry Met Sally—even at $100 million domestic, after a 50 percent exhibitor split, Disney gets $18 million. Generous, yes—but Daenerys, holding all non-theatrical rights, stands to profit far more."
The auditorium emptied; the two rose to leave.
Eisner mentally calculated, then nodded with another rueful smile.
Indeed.
Without Simon's concessions, Disney would never have invested heavily.
Now, Disney's full-court press—two months of TV spots, over a thousand screens at once, prime Easter placement—had secured the stellar results.
Absent those, the film's quality might still have driven success, but nowhere near current heights. And a domestic century markedly boosted ancillary performance.
By typical revenue ratios, overseas, television, and home video would triple or quadruple theatrical—mostly profit, given minimal additional marketing.
Even after fees and costs, Daenerys would recoup production from theatrical alone; everything else pure gain.
In the end, Disney's $18 million fee looked like the shorter end.
Seated in the car waiting outside, en route back to Disney headquarters, Eisner asked, "So, Michael—what do you make of the other Daenerys projects in development?"
"I've read most scripts. Rain Man—I personally shepherded it over a year. Dead Poets Society, Steel Magnolias, others—honestly, they'll all be good films, but commercial performance is uncertain." Ovitz considered. "In this business, no one predicts hits with certainty—but I'm no longer sure that applies here."
Eisner pressed, "You think all their films will match this?"
Ovitz shook his head. "I don't know. But if I were you, I'd pursue distribution on any still-available titles—at minimum, cultivate strong ties with Daenerys."
Eisner nodded, then observed, "Yet from your position, you haven't."
"He's an ambitiously hungry kid," Ovitz said, expression turning reflective. "You know, at our first meeting he hinted at a desire—to return Hollywood to the studio era. Studio era—stars as mere employees, no room for agencies. Impossible. So we're destined to be adversaries."