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.

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,...