For a film aiming for the Oscars, aside from winning over the Academy, the most crucial task is ensuring that the more than six thousand Academy voters outside the organization recognize its value.
Fortunately, Gilbert was not only one of the most well-known directors in Hollywood but also a household name across America and even worldwide. Even if some voters hadn't seen his films, they certainly knew who he was.
Beyond standard promotional campaigns and film critics actively championing Chicago, Gilbert also made full use of his personal connections.
"The Jewish Academy voters—I took a few of them golfing the other day, and they all promised to support you," his father told him upon returning home.
In Chicago, his father had once again taken on a minor role—this time playing a wealthy old man with a few lines.
By this point, his presence in Gilbert's films had become something of an Easter egg. Every time he appeared on screen, it sparked heated discussions among fans.
Gilbert expressed his gratitude. "Thank you, Dad."
"No need to thank me," his father said with satisfaction. "This is your third nomination for Best Director. The Academy won't ignore you.
But the fact that you're staying level-headed, not overestimating yourself, and seriously working on your campaign—that's truly commendable."
His father wasn't wrong. Even as the frontrunner, Gilbert couldn't afford to be complacent. The Oscars had seen their fair share of surprises, especially with the Weinstein brothers as competitors.
However, since Gilbert had become the overwhelming favorite this year, rumors suggested the Weinstein brothers had shifted their focus to other categories.
The primary battlegrounds were Best Picture and the Best Actor and Actress races, which were fiercely contested.
Tom Cruise had been making frequent high-profile appearances lately, all in an effort to strengthen his presence in voters' minds.
At the same time, the Weinstein camp had unleashed the media to launch an aggressive smear campaign against Cruise, attacking both his acting abilities and his religious beliefs.
One newspaper went so far as to label him a puppet controlled by the Church of Scientology, claiming he was being used to recruit Hollywood's most attractive men and women into the church.
Even more outrageously, some tabloids spread the rumor that Nicole Kidman's unborn child wasn't actually Cruise's but rather fathered by the Church of Scientology's leader.
These relentless negative stories aimed to tarnish Cruise's reputation and turn the Academy voters against him.
Strangely, though, the same tactics weren't used against Naomi Watts. The reason? Gilbert was known for his ruthless retaliation.
Last time, when someone tried to target Naomi Watts, Gilbert had gone as far as to take down Mel Gibson.
Harvey Weinstein had a long history of dirty dealings, while Gilbert—aside from having many girlfriends—kept his own record relatively clean. Weinstein knew that if he went after Watts too aggressively, Gilbert might retaliate in ways that would be difficult to escape.
And Weinstein had no illusions about his own survival skills. If Gilbert decided to strike back without restraint, Weinstein doubted he would be able to slip through the net unscathed.
Ultimately, while Weinstein controlled Miramax and was a dominant force in independent filmmaking, he was still insignificant compared to a top-tier director like Gilbert.
More importantly, Miramax was a subsidiary of Disney, operating independently but still answerable to the Disney board.
If Weinstein made a move against one of Disney's most valuable live-action filmmakers, would the Disney executives tolerate it?
Robert Iger, the smiling tiger, might appear mild-mannered, but his methods were just as ruthless as Michael Eisner's.
With all these factors in mind, Shakespeare in Love had focused its Oscar campaign on the Best Picture and Best Actor races.
The Best Director category had been completely ceded, and for Best Actress, Gwyneth Paltrow was left to handle her own public relations with minimal backing from Weinstein.
Weinstein even advised Paltrow to give up on this year's Oscars and wait for another opportunity, warning her that Naomi Watts was coming in strong.
This infuriated Paltrow. She had thought the award was within her grasp, only to have Weinstein surrender before the fight had even begun.
That useless, spineless fat man—not only was he weak, but he wasn't even a third as enduring as Gilbert.
And to make things worse, he wasn't even pleasing to look at.
Paltrow was fuming—and filled with regret.
If she hadn't broken up with Gilbert back then, would Chicago's lead role have been hers instead?
Clinging to this thought, Paltrow reached out through her godfather, Steven Spielberg, to arrange a meeting with Gilbert.
At a small café, Gilbert found himself face to face with Paltrow once again.
Over the past few years, Gwyneth's career had been thriving, and with that success, her temper had also grown worse. Her notorious diva attitude had become widely known throughout Hollywood.
It seemed that all of Gilbert's past advice had gone completely unheard by her.
"Long time no see, Gwyneth," Gilbert greeted politely as he sat across from her.
Gwyneth rolled her eyes. "We saw each other not long ago. It hasn't been that long."
"True," Gilbert nodded slightly. "So, what brings you here?"
"Let's order something to drink first. What do you want?" Gwyneth seemed to have matured somewhat. In the past, she would have jumped straight to the point without hesitation. But now, she was actually trying to ease into the conversation.
Gilbert ordered a glass of water. However, after only a few moments of small talk, Gwyneth couldn't hold it in any longer. It was clear that subtlety was not her strength.
"I'll be direct—Gilbert, I need this award," Gwyneth said, locking eyes with him, taking in his handsome face.
They hadn't seen each other in person much over the past few years, though she had often come across his image in the media. Now, sitting in front of him, she could see that Gilbert had clearly become more mature.
A hint of regret crossed her mind. If they had dated instead of just being friends back then, would everything that Naomi Watts had now belong to her instead?
But regret was pointless. Knowing Gilbert's personality, she was certain he wouldn't humor her request.
Besides, she wouldn't be able to accept it even if he did. There were too many women around him, each one more beautiful than the last.
Gwyneth was strict with others but lenient with herself. She felt entitled to date multiple men, yet she couldn't tolerate Gilbert having multiple women.
Of course, given that they had no relationship now, it wasn't her business to interfere.
Hearing her plea, Gilbert simply smiled and shook his head. "I know you need this award, but Naomi needs it too. She's just one Oscar away from surpassing Julia Roberts to become the top actress in Hollywood."
Naomi Watts was someone Gilbert had personally helped rise to fame. When he first met the petite actress, she was still introducing herself as Nicole Kidman's best friend.
At that time, she was barely scraping by in Los Angeles—financially unstable, without proper food, shelter, or health insurance. She worked in restaurants while auditioning, nearly giving up on her acting career altogether.
Then she met Gilbert. She seized the opportunity he offered, gradually landing roles, moving from supporting parts to leading roles, step by step, until she reached her current status.
Though Gilbert had many women at his estate, Naomi Watts was perhaps the only one who had truly weathered the storms with him.
That was why she held a special place in his heart—he always prioritized her when good opportunities arose.
Naomi Watts was already thirty years old, soon to turn thirty-one—two years older than Gilbert.
For actresses, career longevity was often much shorter than for their male counterparts. After thirty, their marketability typically started to decline.
This Oscar was a golden opportunity for Naomi Watts. There was no way Gilbert would give up such a chance just because of a few words from Gwyneth.
Gwyneth's eyes darkened with frustration. "So you really won't step aside?"
Gilbert shook his head. "No. I heard you and Harvey have been working together quite well. I'm sure you'll have plenty of other opportunities.
As for me, my filmmaking style doesn't align with the Oscars in the long run. You'll have many chances in the future."
Gwyneth's expression turned sour. Instead of calming her, Gilbert's words only made her angrier.
She abruptly stood up, her face flushed with irritation. "Fine. Let's see who gets the last laugh."
With that, she stormed out of the café without waiting for Gilbert's response.
Gilbert merely shrugged. Competing for awards always came with rivalries—it was inevitable. Since things were bound to turn ugly, he preferred to make his stance clear.
Meanwhile, Chicago had accumulated a total of $142 million at the North American box office. Having premiered on the last weekend of December, the film had been in theaters for over two months.
While its box office potential had mostly dried up, it was still playing in a few hundred theaters, with screenings expected to continue until the Oscars.
If it won awards, its theatrical run would likely expand again, allowing it to rake in even more revenue.
With a production budget of $20 million and total marketing costs pushing the overall investment to just over $40 million, the film had already turned a profit through box office earnings alone.
But the biggest surprise for the production team was the success of Chicago's soundtrack, produced in collaboration with Warner Records. The album had sold 8.5 million copies across the U.S.
Though it didn't quite match Titanic's record-breaking soundtrack sales of over 10 million copies, it was still an impressive feat for a musical.
Last year, during The Matrix's massive success, Charlize Theron's Trinity action figure had generated over $8 million in sales.
Now, following Chicago's release, Naomi Watts and Catherine Zeta-Jones' figurines were experiencing similar success, with total sales also surpassing $8 million.
A musical film primarily targeting the Oscars had unexpectedly become a profitable venture in merchandise sales, sparking envy across Hollywood.
Reports suggested that several second-tier and even major studios were now rushing to develop their own musical films, hoping to capitalize on the genre's renewed popularity. Some critics were even proclaiming the return of the golden age of musicals.
But in reality, that was just an illusion—the musical era would never truly return.
However, if a few high-quality musicals were produced during this window of opportunity, they could still turn a considerable profit.
Beyond its commercial success, Chicago had also made a significant impact on Broadway.
During the film's peak popularity, Broadway theaters were experiencing an overwhelming surge in ticket demand, with many shows selling out completely.
Most importantly, Chicago had introduced a younger audience to Broadway.
Even if only a small portion of these new viewers became regular theatergoers, it would still be a huge win for Broadway's business.
In that sense, Broadway owed a great deal of gratitude to Gilbert.
Without him, Broadway's name recognition might have remained high, but its audience numbers had been steadily declining for years. In just a few more years, some theaters might have struggled to stay open.
With its outstanding commercial performance, Chicago had fulfilled its mission. Now, all that remained was the Oscars.
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