What’s the Worst Best Picture Winner of the 21st Century?

Given that we are mere weeks away from Oscar nominations, here’s an old 10.09.23 post that’s been re-edited for 2026 purposes.

Looking back at the Best Picture winners of the last 25 years, you notice only a handful of truly deserving films: “No Country for Old Men” and “The Departed” come to mind. I also have no issues with the Academy giving the top prize to “Gladiator,” “12 Years a Slave,” “Birdman,” “Spotlight,” and a few others.

The ’90s Academy seemed to have a slightly better set of winners: “The Silence of the Lambs,” “Unforgiven,” “Schindler’s List,” and “Titanic.” Then again, “Dances with Wolves” over “Goodfellas”? “Forrest Gump” over “Pulp Fiction”? “The Truman Show” was not even nominated?

This morning, I had a friendly argument with a well-honed NYC film critic. She kept hammering on about how “Green Book” was the worst Best Picture winner of her lifetime. I disagreed. “It’s ‘Crash,’” I replied, “and it’s not even close.”

Then I quickly realized how we now live in a world where “Everything Everywhere All at Once” is a Best Picture winner — hell, even The Daniels are best director winners — and although I am no fan of that film (and yes, it is one of the worst winners of the last 25 years), at least that film had ambition to spare.

If you ask critics, they’ll most likely mention “Green Book.” Before—and especially after—it won Best Picture, that film caused the kind of backlash only exceeded by “Emilia Perez.” Anybody who liked the film must have been a racist. The NAACP’s president agreed with that sentiment. Viggo Mortensen had to step in to claim that accusations of racism were “unfair” and “dangerous.” The winter of 2019 was a wild time to cover the Oscars.

The amount of media vitriol that the film garnered was over-the-top. The L.A. Times’ Justin Chang wrote a piece with the headline: “‘Green Book’ Is the Worst Best Picture Winner Since ‘Crash.’” Chang wrote:

“Green Book” is insultingly glib and hucksterish, a self-satisfied crock masquerading as an olive branch.” Calling it “an embarrassment […] It reduces the long, barbaric and ongoing history of American racism to a problem, a formula, a dramatic equation that can be balanced and solved.

Nope. “Green Book” is nowhere near the same mediocre league as the 2006 Oscar winner “Crash” — a film that proudly declared itself anti-racist even though it trafficked in simplistic, contrived and racially-tinged caricature tropes. Hell, “Green Book” is also better than other much-debated 21st-century winners such as “Chicago,” “The Artist,” and “Argo.” And don’t even get me started on the weak crop of winners we got during the pandemic era (“Nomadland,” ‘EEAO,’ “CODA”)

Now it’s your turn—worst film to be crowned by the Academy these last 25 years. There are many candidates.