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Worst Oscar Robbery of All Time: Harvey Weinstein Is the Culprit Behind Steven Spielberg’s Movie Losing the Best Picture?

Sometimes, the greatest victories come at the cost of the most bitter truths. This line, though perhaps a little melodramatic, captures the essence of what went down at the 1999 Oscars when Shakespeare in Love snatched the Best Picture award right out of the hands of Steven Spielberg’s Saving Private Ryan

The 1999 Oscars marked one of the most controversial moments in Hollywood history.
Saving Private Ryan (1998) [Credit: Paramount Pictures, DreamWorks Pictures]

It was supposed to be Spielberg’s moment—his magnum opus about World War II, Saving Private Ryan, had critics and audiences on their knees in awe. Yet, the award went to Shakespeare in Love, a light-hearted period comedy. But this wasn’t just a regular upset; it was a strategic victory reportedly orchestrated by none other than Harvey Weinstein.

Let’s take a deeper look at how one man’s relentless campaign reshaped Oscar campaigning and changed the industry forever.

Shakespeare in Love: Harvey Weinstein’s aggressive campaign that stunned Hollywood

Before Harvey Weinstein, Oscar campaigning was a quieter, more subdued affair. Sure, studios always worked hard to promote their films, but Weinstein took it to an entirely new level. He turned the Academy Awards into a battlefield, and Shakespeare in Love became his weapon of choice. Michael Schulman, author of Oscar Wars: A History of Hollywood in Gold, Sweat and Tears, informed BBC Culture:

He turned Oscar campaigning into much more of a bloodsport.

Steven Spielberg’s Saving Private Ryan seemed like a shoe-in for Best Picture. The movie was epic, emotional, and highly praised. Spielberg even took home Best Director—everything was aligned for a victory. Yet, when Harrison Ford announced Shakespeare in Love as the winner, it was as if time had stopped. The gasps in the room were deafening.

Harvey Weinstein reportedly masterminded an aggressive Oscar campaign for Shakespeare in Love.
Gwyneth Paltrow in Shakespeare in Love | Credit: Miramax Films

Weinstein’s campaign for Shakespeare in Love was legendary. He planted negative stories about Saving Private Ryan, slyly suggesting it lost momentum after the first 25 minutes. While Spielberg focused on the art and integrity of his film, Weinstein was reportedly building a political-style campaign. And it worked.

Miramax’s aggressive tactics, from constant phone calls to Academy members to creating a buzz in every corner of Hollywood, made sure Shakespeare in Love stayed at the forefront of voters’ minds.

Schulman stated:

It was a shock, but it was also a confirmation of what everyone had been primed to believe, which was that the Miramax campaign was out of control.

In the years following this shocking win, the landscape of Oscar campaigning was never the same. 

The birth of the relentless Oscar campaign: Harvey Weinstein’s ‘bully masterpiece’

Harvey Weinstein’s pioneering tactics transformed what was once a cordial, low-key process into a grueling, months-long endurance test. Gone were the days of casual industry screenings and polite ads in trade papers. Weinstein reportedly introduced the concept of in-your-face campaigning, where actors were required to participate in a barrage of screenings, Q&As, and party appearances. 

Shakespeare in Love unexpectedly beat Saving Private Ryan for Best Picture.
Harvey Weinstein. | Credits: Image by David Shankbone / Licensed under CC-BY-3.0 / Wikimedia Commons.

As one publicist told Vanity Fair:

It all began with Harvey. I don’t remember ever feeling pressure like that from other studios. He was like, ‘Can you do these radio call-ins all morning?’ He calls the clients directly and guilts them. He really is a beast.

Former Miramax executive Mark Gill described it as if the movie’s release was only an opening salvo for the publicity requirements placed on actors at the studio: “That was just ‘Good morning,’” said Gill, adding, “You’ve got three months of shaking hands and kissing babies in you.”

This aggressive campaign style was met with some resistance, especially from Steven Spielberg, who wasn’t interested in begging for trophies. He didn’t want to play the game, while Weinstein was reportedly more than happy to force Shakespeare in Love into the limelight—by any means necessary.

Ultimately, Harvey Weinstein’s role in Shakespeare in Love’s victory was one of the most controversial chapters in Oscar history. We can’t help but feel that the Oscars, a once-celebrated celebration of artistry, became a corporate battleground from that point on. It’s a lesson Hollywood will never forget, even if the true cost of that win is still felt today.

Shakespeare in Love is available to rent on Amazon Prime Video.

Saving Private Ryan is streaming on Netflix.

This post belongs to FandomWire and first appeared on FandomWire

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