Harvey Weinstein and the Oscars’ Game-Changing 1999 Battle

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Let’s take a trip back to the 1990s Oscars—a decade that was anything but boring if you had any interest in movies, awards, or the soap opera that goes with both. The Academy Awards have long been a combination of glamour, creativity, and ego, but the 1990s took it to an entirely new level. The decade yielded some of the most memorable—and contentious—Best Picture Oscars of all time.

The Ascension of the Indies: Miramax and the Underdogs

Before the 90s, the Oscars were pretty much a sandbox for major studios. Big bucks, big names, big marketing campaigns. Along came Miramax, the independent studio that was rattling the cage with movies such as The Crying Game and Pulp Fiction. Under the leadership of Harvey Weinstein, Miramax didn’t just want to play—they wanted to win, and they were willing to pull out all the stops to do it.

Harvey Weinstein’s Campaign Strategies: Confrontational and Unabashed

Oscar campaigning had existed before, but Weinstein turned it to an extreme. Ditch the nice lunches and screenings—this was full-blown strategic warfare. The motto was simple: if you’re the underdog, you can’t just wait around and expect things to work out. You campaign like it’s a political campaign. That included constant messaging, pushy outreach, and a willingness to bend—or disregard—unwritten protocol.

For My Left Foot, Miramax screened for politicians and had Daniel Day-Lewis appear publicly endorsing the Americans with Disabilities Act. Miramax employees made phone calls to Academy members every awards season to deliver VHS copies, arranged special screenings in nursing homes, and had their stars appear on as many panels, parties, and lunches as they could.

The 1999 Showdown: Shakespeare in Love vs. Saving Private Ryan

Then along came 1999. Steven Spielberg’s Saving Private Ryan was the lock to beat for Best Picture—a riveting war drama with an awe-inspiring opening scene and critical success. Spielberg even took home Best Director that year, traditionally a surefire indicator that Best Picture would be his as well.

But Miramax had other ideas. Shakespeare in Love was a last-minute challenger—light, romantic, witty, and smart. It was a love story instead of a war story, and Hollywood always had a fondness for films about itself. When the nominations were revealed, Shakespeare in Love had 13 nominations against Saving Private Ryan’s 11.

Miramax mounted a high-octane effort. Mark Gill, who was then Miramax’s LA President, called it “absolutely murderous the whole way through.” Saving Private Ryan was attacked by Weinstein in interviews, implying the movie stalled after its opening, according to sources. Spielberg would not play that game, but DreamWorks kicked up its campaign with ads in industry publications.

When Harrison Ford declared Shakespeare in Love Best Picture, the crowd erupted. Gwyneth Paltrow shrieked with joy, Weinstein shoved his way to the stage, and Spielberg beat a hasty retreat, bypassing the press. The victory became Hollywood’s watercooler talk—primarily for all the wrong reasons.

The Fallout: How Oscar Campaigning Changed Forever

That evening transformed everything. Studios understood they had to campaign Miramax-style. Suddenly, awards season turned into an arms race, with strategists, PR teams, and constant outreach the new norm. Negative reports about rivals began appearing in the media, and the Academy tightened rules to avoid anarchy.

In the succeeding years, campaigns only grew more ferocious. DreamWorks went all out and succeeded with American Beauty, then Gladiator in 2001. Miramax’s playbook became the go-to of the industry. Studios spend as much—or even more—on campaigns as on actually producing the movies. Netflix was said to have spent as much as $60 million attempting to get a Best Picture award for Roma. Consultants now receive fat salaries and bonuses based on nominations and wins.

Why All the Fuss? Ego, Recognition, and Insecurity

Why do the studios spend millions on Oscar campaigns if awards don’t seal a movie’s legacy? For some, it’s ego and bragging rights. According to Hollywood executive Terry Press, the business is all about insecurity, and nothing calms it like a gilded gold statue.

Even 25 years after Shakespeare in Love’s shock win, Oscar campaigning is a high-stakes, high-drama game. The strategies may have changed, but the hunger for validation—and the adrenaline of competition—have never been more intense.

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