As the noticeably lackluster 1987 summer blockbuster season drew to a close, the two films connected to Simon wrapped up one after another.
On August 6, after a 17-week run, The Butterfly Effect officially exited North American theaters, its final box office tally locked at $116.95 million.
Soon after, to free up screens for the new release No Way Out, Orion pulled Run Lola Run from all theaters on August 13. From February 13 to August 13, the film had played for exactly half a year, amassing a cumulative gross of $223.77 million.
By August, only three films had crossed the $100 million mark domestically this year—and two of them came from a young man who'd debuted just a year ago. It was nothing short of a miracle. Just as the media buzzed in June when both films hit nine figures, the sequential pull from theaters sparked another mini surge of news about Simon.
But Simon had no time to pay attention to any of it.
While shooting Pulp Fiction, he was also juggling post-production on Final Destination and prepping When Harry Met Sally. At the same time, his stock index futures operations demanded a ton of his focus.
The tense month of August flew by in this whirlwind, slipping past halfway before he knew it.
Robert De Niro wrapped his scenes in early August, and the cameo appearances by Robert Redford, Nicole Kidman, and others followed suit. Thinking everything would sail smoothly, Simon hit the toughest snag of production in the last week of August: Madonna.
Her second film, Who's That Girl, had just hit North American theaters on August 7.
If she'd at least tried to act seriously in last year's Shanghai Surprise, in Who's That Girl, the Queen had completely given up, her over-the-top, exaggerated performance practically guaranteeing her the Razzie for Worst Actress next year.
By the time she got to Pulp Fiction, Her Majesty's flair for the dramatic hadn't fully faded, stretching what was supposed to be a three-day shoot into five.
Janet, Nicole, and the other female leads had all delivered performances that thrilled Simon—he wasn't about to lower his standards for the "Pumpkin" role that kicked off the film. So these past few days, he'd gone toe-to-toe with the Queen.
If he couldn't wrangle her performance, Simon Westeros might as well hang it up.
Today was August 28, a Friday.
In a fast-food joint in south Santa Monica.
Over these five days, crew members who'd worked with Simon since Run Lola Run finally witnessed the director's "frenzy." But it had nothing to do with the shoot going south—instead, he was personally demonstrating, shot by shot, how "Honey Bunny" should play out.
The tall, handsome director—every female crew member's dream guy—cross-dressing as a manic female robber was a sight that had everyone stifling laughs.
By the counter in the diner.
The whole crew circled around, patiently waiting as Simon walked Madonna through the scene. Even Sean Penn stood by with interest, not batting an eye when Simon gallantly handed his wife a bottle of water. Having read the script closely, he knew exactly why Simon was doing it—and couldn't help admiring how the guy pulled out all the stops for this final scene.
A moment later.
The scene everyone had been buzzing about for days unfolded again.
Simon gestured and explained to Madonna, then grabbed her prop revolver, hopped onto the counter without a care, and shrieked at the empty air where no actors were positioned: "Let him go! Let him go! Let him walk, or I'll kill you! Let him go..."
After the demo, Simon held the pose on the counter, addressing Madonna below: "Maggie, see? Like that. Squat down a bit—robbery gone wrong, you're scared inside, even on the verge of breaking. So, best if your legs shake a little, like this."
He demonstrated earnestly before jumping down.
Madonna had been miffed at first about playing such a crazy woman. But seeing Simon throw dignity aside to show her how, she'd developed some respect for this under-20 director who'd already sparked two box office miracles. These past days, she'd let loose completely.
It was just a role, after all.
And hey, people called her a madwoman anyway—might as well go all in.
Once Simon was down, Madonna took the prop revolver, brewed her emotions a bit, and jumped up: "Let him go! Let him go! Let him walk, or I'll kill you! Let him go..."
"Legs—shake 'em... Too obvious, tone it down... Okay, come on down," Simon said. As she hopped off, he took the revolver again and demoed once more.
They went through this routine several times until Simon was satisfied. Subtly, he handed her another bottle of water: "Here, Maggie, have some more, then we'll roll."
Madonna took it, shooting him a sidelong glance laced with teasing: "Kid, is this your idea of flirting? Gotta say, it's pretty lame."
Even so, she tipped her head back and chugged half the bottle.
Simon conjured yet another bottle but held off giving it to her, instead directing Sean Penn, Samuel L. Jackson, and the extras to take their marks.
If they nailed this today, the Queen's scenes—and Sean Penn's diner bits—would wrap smoothly.
With that hope, the whole crew perked up.
The first few takes naturally fell short of Simon's vision, and in between, he got another bottle of water into Madonna.
Half an hour later, jumping down from the counter, Madonna headed straight for the bathroom—but Simon blocked her.
"Hey, kid, I gotta hit the bathroom. You planning to come with?" She arched a brow in jest, then got it, glaring at him: "You did this on purpose?"
Simon neither confirmed nor denied: "Maggie, stick it out and finish the scene—I'll treat you and Sean to dinner tonight, how's that?"
Madonna clutched her stomach, her eyes darting: "Real urgent, huh? You want to see me make a fool of myself?"
"Fine," Simon surrendered: "Name your terms."
Madonna held up two fingers: "Add two more songs."
"I'm just a film director, Maggie," Simon grimaced. "Besides, songs need inspiration—can't just crank 'em out on demand."
"You nailed 'Flight of the Bumblebee' like a pro, and Run Lola Run's score was killer—I've got faith in you," Madonna said. Seeing him unmoved, she pushed forward: "Then I'm hitting the bathroom."
Simon blocked her: "Two total, no more."
"Deal," Madonna nodded briskly, then added: "But you gotta hurry—I can hold it for half an hour, tops."
Simon shook the water bottle: "If you can't, go—but I need you in this state all afternoon. Might even run overtime."
Madonna balked: "Three."
"Only two, but I guarantee you'll love 'em."
Her eyes rolled: "Be my guitarist at my next concert."
"No way!"
"Just one show—cameo style. Quick rehearsal, done. And kid, I'll pay you," Madonna grew more excited. Seeing him hesitate, she pushed again: "Then I'm going to the bathroom."
Simon caved: "Fine, one show."
Her eyes spun again: "Holding it in's tough..."
Simon stepped aside: "Just go to the bathroom."
But Madonna didn't, relenting with mock reluctance: "Fine, fine—you're such a cheapskate."
People holding it in are often at their most vulnerable, so the Queen nailed the emotions Simon wanted with minimal effort. In the takes that followed, everyone felt she captured the failed robber's bluster masking inner terror and near-breakdown perfectly.
They inevitably ran an extra hour, but after a week, Madonna and Sean Penn's diner scenes wrapped smoothly.
After wrap, Madonna reminded Simon to hurry on those promised songs before leaving with Sean.
Tomorrow was the weekend.
Simon got back to Palisades around seven p.m.
Janet had thoughtfully prepped dinner. Over the meal, she mentioned Noah Scott had called three times since five.
Simon only remembered the S&P 500's pre-crash peak topped 330, but not the exact figure.
So on August 19 last week, when it hit 325, he'd started unwinding Westeros's 10,000 long contracts. On August 25—this Tuesday—it broke 330, and he pushed Noah to speed up the unwind.
Per the sell schedule, the 10,000 longs should've cleared today.
But.
This time, Simon hadn't rushed Noah to build shorts.
After dinner, he headed to the study, Janet trailing. After three-plus months, though she had a rough idea, she was dying to know exactly how much her man had made.
He called back; Noah seemed extra enthusiastic today.
They chatted a bit before Noah faxed over the post-unwind reports and accounts.
Today's close: S&P 500 at 337.
With the July-August surge, building at lower levels was tough—the 10,000 averaged 316 entry, 332 exit.
Overall, just 16 points per contract—below prior averages. But still, the unwind netted $80 million profit.
After fees, Westeros's account now held $278.56 million.
Short of his $300 million goal, but three and a half months turning $75 million into $278.56 million—nearly 300% return—was a windfall even Wall Street's elite couldn't match easily.
Simon's call with Noah was evening in L.A., but past ten p.m. in Chicago.
In a villa in Naperville's affluent suburbs outside Chicago, Noah Scott had sent his live-in girlfriend away for the night. Now it was just him and two men in their fifties.
One was Nelson Scott, Noah's father and American Express VP; the other, ruddy-faced, was AmEx CEO James Robinson.
Once Noah hung up, his father asked: "Well?"
Noah shook his head: "Still waiting for instructions."
"Quite the cautious kid," James Robinson said, flipping through a thick file of Westeros's recent trades. "But turning $200 million in three months? That caution's earned. Noah, what's your take on his next move?"
Noah pondered: "Delivery month's coming—September'll be volatile. And no simultaneous rebuild on sells, so either he's cashing out... or going short. After all, most think the market's topped."
James shook his head: "Folks thought that back in June, built shorts—but the kid pocketed $200 million. Tsk, $200 million. And his Hollywood run—saw those two films myself, damn good, grosses shocked everyone. Where'd that kid even come from?"
"Heard he spent half a year in a San Francisco psych ward and came out like this," Noah joked, drawing smiles, then added: "So, Mr. Robinson, what's our next play?"
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