How Timothée Chalamet Can Turn a Loss Into an Oscars Win

I’d like to start this week’s newsletter with an embarrassing confession: I hadn’t seen “Titanic” before last weekend.

In my defense, I’m 24, and cinema predates me by 100-and-some years. There’s always more to cross off my list. When I got to a certain age without seeing James Cameron’s Oscar-winning, record-breaking epic, I decided I would wait to watch it until I could see it in a movie theater.

So that’s how I spent my Valentine’s Day — going to the Gardena Cinema to watch “Titanic” on the biggest screen possible. It was well worth the wait.

I couldn’t help but feel a bit of serendipity sitting in that theater, watching a young Leonardo DiCaprio star in his first Best Picture winner. Every day, it seems more likely that “One Battle After Another” will be his third (don’t forget “The Departed,” which won between the two).

“Titanic” reminded me of Hollywood movies at their best. It’s massive in scale, technically precise, made for the big screen. At the same time, the story remains intricate, grounded and moving. I became a puddle of tears throughout the third act.

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Something magical happens when every element of a movie comes together — direction, casting, performances, writing, costume design, art direction, music. The film becomes eternal. It earned those 11 Oscars (though somehow it didn’t get a screenplay nod).

2025 didn’t have a “Titanic”-sized hit, but some of this year’s Best Picture contenders did fill me with similar awe.

One of the great powers of the Oscars is their ability to bring broader audiences to smaller films, and I will always defend a good modest-budget winner. Still, some of the my favorite Best Pictures are cultural hits that are ultimately undeniable, filmmaking done at a giant scale without sacrificing quality — movies like “The Lord of the Rings: The Return of the King” and “Oppenheimer.”

I’ve lived my entire life with Cameron’s blockbuster in the public consciousness, but for three hours, I felt like I was watching a brand-new movie.

Maybe this year’s winner will do the same decades down the line.

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How Bette Davis turned a loss into a win

Bette Davis’ first Oscar win came with one big critic: Bette Davis.

Her tangled Oscar saga began in 1934, when, wanting to prove her abilities as an actress, Davis begged Jack Warner, who owned her contract, to let her play Mildred Rogers in an adaptation of W. Somerset Maugham’s “Of Human Bondage” over at RKO Radio Pictures.

Davis didn’t want to be another doe-eyed female lead, as could be found in many other ‘30s pictures. Instead, she played Mildred (a part other actresses were scared to take on) with fire and a mean streak, earning sweeping critical acclaim for her attention-stealing turn.

James Baldwin put it best when he wrote about Davis’ Mildred in his semi-autobiographical “Go Tell It On the Mountain”: “Nothing tamed or broke her, nothing touched her, neither kindness, nor scorn, nor hatred, nor love.”

But Davis became what history considers the first Oscar snub. Her failure to be nominated for “Of Human Bondage” caused such an outcry that the Academy announced it would allow write-in votes on the final ballot. 

Still, Davis ended in fourth place, losing to Claudette Colbert, who played Ellie Andrews in Frank Capra’s “It Happened One Night” (one of three films to win the “Big 5” Oscar statues for Picture, Director, Actor, Actress and Screenplay). Funnily enough, Capra wanted Davis to play Ellie, but Warner wasn’t going to loan her out twice back-to-back.

Davis wouldn’t stay out of the Oscar race for long. A year after the “Of Human Bondage” snafu, she won Best Actress for “Dangerous” (beating Colbert for a change, this time for “Private Worlds”).

“It was true that even if the honor had been earned, it had been earned last year,” Davis wrote in her autobiography “The Lonely Life.” “There was no doubt that Hepburn’s performance deserved the award.”

Davis wasn’t satisfied. She felt her win was little more than a consolation for the previous year’s screw-up. “These mistakes compound each other,” she wrote in her autobiography, “like the original lie that breeds like a bunny. Now (Hepburn) should get it next year when someone else may deserve it.”

Hepburn did not win the next year (she had already won a statue in 1934 for “Morning Glory” and wouldn’t get nominated again until 1941 for “The Philadelphia Story”). Davis would go on to become the first person to receive acting nominations five years in a row (1938-1942) and the first to pick up 10 acting nods total.

Yet Davis was right when she pointed out that wins don’t exist in a vacuum. This fact informed TheWrap’s Awards Tracker, which analyzes the different signs that indicate an Oscar is coming someone’s way.

But the numbers can’t track how past years affect present sentiment (at least, not yet). Sometimes, losing an Oscar (or a few) gives you a bit of a push when a new nomination rolls along. Other times, it feels like people who already have a statue (like Hepburn back in ’36) need to justify why they deserve another. This mainly affects actors and directors.

Davis’ thought process (once called “Bunny Theory” by Michael Schulman at The New Yorker) has shown up several times in Oscars history since the 1930s. Perhaps the biggest example came in the early 2000s, when Russell Crowe immediately won Best Actor in 2001 for “Gladiator” after losing in 2000 for “The Insider” (a tight three-horse race between Crowe, Denzel Washington for “The Hurricane” and Kevin Spacey, who won for “American Beauty”).

Crowe got nominated for Best Actor again in 2002 for Best Picture winner “A Beautiful Mind,” though the prize went that time to Washington for “Training Day” — no doubt influenced by his recent loss and Crowe’s recent win.

But there are other ways that the Oscars of the past can affect the awards of the present.

Will Timothée Chalamet get his first Oscar?

Though it’s a different situation than Davis’, a similar thought process explains why I’m so resolute in my prediction that Timothée Chalamet will be this year’s Best Actor winner for “Marty Supreme.”

If you look at the Awards Tracker, you will see that none of the five actors have great odds at winning this prize (Chalamet leads with 25%). I can envision a world where any of them walks away with the statue.

But I keep thinking about the fact that, on top of his Golden Globes and Critics Choice wins, Chalamet was widely considered the runner-up for Best Actor just last year with “A Complete Unknown.” He even won the prize at the Actor Awards.

I believe Chalamet’s turn in “Marty Supreme” is one of the best performances of 2025. And returning to the awards race so soon after his Bob Dylan run doesn’t hurt his chances.

Chalamet is competing against Leonardo DiCaprio, who arguably benefitted from some awards losses in 2016. Before “The Revenant” got him the gold, DiCaprio lost the Oscar four times. He didn’t even get nominated for the two Best Picture winners he starred in. That made a strong case in the 2010s.

The “It’s time” narrative can be a powerful thing. This is also relevant to Paul Thomas Anderson, a celebrated writer/director with a 30-year career who has gone 0 for 11 at the Oscars coming into 2026. I love “One Battle After Another” and think PTA makes a deserving winner — but the build-up certainly helps his case.

The main difference between Chalamet and DiCaprio or PTA is, of course, his age. If he would’ve won Best Actor last year for “A Complete Unknown,” he would’ve been the youngest winner in the category (a record Adrien Brody set in 2003 with “The Pianist” and kept by beating Chalamet last year for “The Brutalist”).

If he gets the Oscar this year, Chalamet will still be the second-youngest winner, defying the Academy’s reluctance to give that award to young men. “Marty Supreme” also marks only Chalamet’s third acting nomination — so not quite the same as DiCaprio’s fifth.

Still, momentum can be a powerful thing. If any voters felt that Chalamet deserved a win last year, that may give him the extra push he needs to get the gold in March.

Make-up and career achievement awards aren’t always bad. History has been pretty kind to Davis’ “Dangerous” win, even if she was not kind to herself. It’s a well-regarded early Oscar win that’s more memorable than most of the 1930s honorees. 

But Davis was among the first to show how an Academy Award loss can turn into an Oscar win. We’ll see where that happens this year.

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