Inside the Oscar Knife Fight: How Best Picture Is Really Won (And Lost)

Legendary awards strategist Tony Angellotti reveals how the race is fought — and why losing can cost you everything

In the annals of modern Oscar history, few loom as large as Tony Angellotti — the legendary publicist and founder of The Angellotti Company, who has shepherded multiple movies to best picture wins, including Shakespeare in Love and Oppenheimer.

“I’ve had the pleasure of working on six best picture winners. There’s a sense that it’s an unstoppable train — it’s just fun,” Tony tells me on this week’s Rushfield Lunch. “But if you’re in a position where you’re battling (to win), the pressure mounts. I went grey prematurely in life. Because if things don’t go well, you may not work with that client again. I’ve known a number of people who have been fired after unsuccessful Oscar campaigns. You’d be surprised how many filmmakers have just unloaded after losing.”

But it’s not just the filmmakers who take the game of Oscar so personally. Tony was backstage when Shakespeare in Love defeated Saving Private Ryan at the Academy Awards in 1999 — one of the most unexpected upset wins in the show’s history — and recalls how someone from the Saving Private Ryan team turned to him and said simply, “Don’t ever talk to me again.”

“It wasn’t our intention to make other people unhappy,” he says, “but that’s when you talk about the awards race being a knife fight. That’s what it became.”

Saving Private Ryan is often thought of as one of the best movies to not win best picture — a list that also includes this year’s presumed runner-up Sinners.

“Oftentimes, you have to also understand what the competition is in any given year. Saving Private Ryan would have won in another year,” he says, noting how three of the five best picture nominees in 1999 were set during World War II (Life Is Beautiful and The Thin Red Line being the other two), while Shakespeare in Love was the lone light-hearted contender. “If Private Ryan had been in a year without other war films in contention, I think it would have taken the day easily.”

For much, much more from Tony — including his thoughts on the state of the Oscars, why Anora’s best picture win caught him off guard and what he’s learned from years of awards campaigns — watch our conversation above.