When the Academy of Motion Picture Arts and Sciences first tried to give Peter O’Toole a trophy, the then 70-year-old film icon took pen to paper to politely decline.
This 2003 prize, he knew, wasn’t for a particular movie role: It was an honorary Oscar that would recognize his overall career achievement, after seven prior nominations for best actor — and zero prior wins. Since he was “still in the game and might win the lovely bugger outright,” O’Toole pleaded, “would the Academy please defer the honour until I am 80?”
It may have sounded a little sad — how many more starring roles did he realistically imagine he still had ahead of him? — but it showed that O’Toole understood the essential game of the Oscars: Sometimes voters pick the man who truly gave the best performance. Often, though, it’s simply he who has waited the longest.
That dynamic is in play again in this year’s unusually competitive best actor race, where the three top contenders (of five nominees total) all know a thing or two about waiting their turn:
- Leonardo DiCaprio, 51, was considered the most overdue of his generation when, 22 years after his first nomination, he finally won in 2016 for “The Revenant” — no one’s favorite Leo flick, frankly, but after losses to senior thespians like Tommy Lee Jones and Matthew McConaughey, it was his turn, darn it! Now his endearing semi-comic role as a washed-up radical in “One Battle After Another” has many thinking DiCaprio, a favorite of Hollywood’s top directors, deserves another sooner or later.
- Timothée Chalamet, freshly 30 and already on his third nomination, could also win for his manic turn in the ping-pong epic “Marty Supreme” — though many would consider it a consolation prize after academy voters passed over his uncanny channeling of Bob Dylan in the biopic “A Complete Unknown” last year.
- Michael B. Jordan is already a dozen years past his breakout role in “Fruitvale Station,” which first put him in the Oscar conversation; his work in “Creed” kept him there. Now he is nominated for the first time, at age 39, for 2025’s most-nominated movie, “Sinners,” and gambling sites have moved him into the pole position after his victories at the Screen Actors Guild and other film awards.
On average, male actors win their Oscars when they are significantly older than women actors. Academy voters swoon for the vision of a beautiful ingenue taking home a golden trophy — Gwyneth Paltrow at 26, Grace Kelly at 25, Audrey Hepburn at 24, Jennifer Lawrence a mere 22. They like some seasoning on their best actors; no man has won a leading role Oscar before the age of 29, and most are well into middle age.
Which seems to have been the problem for O’Toole, who was astonishingly clear-eyed and fair-haired in his breakout role at age 30 in “Lawrence of Arabia.” The 1962 movie won the best picture Oscar the following spring and made him an overnight superstar, but he never stood a chance for best actor that year — not when Gregory Peck was in the race.
Not only had Peck crushed it as Atticus Finch in the landmark “To Kill a Mockingbird,” but he was a Hollywood Golden Era favorite who had been passed over for the Oscar four times before during an incredible run of nominated performances two decades earlier, when he was in his 30s. Surely, O’Toole would have a lifetime of Oscars ahead of him.
But then he lost two years later to Rex Harrison, who was kind of undeniable for Henry Higgins in “My Fair Lady,” a far bigger crowd-pleaser than O’Toole’s “Becket.” And Harrison was nearly a quarter-century older, with what was understood to be fewer remaining years to win.
Which was also the case when John Wayne, blustering through the Old West of “True Grit” as a one-eyed drunken U.S. marshal, won the Oscar in 1970. Was it a heavier lift than O’Toole’s “Goodbye, Mister Chips”? Who cares, everyone knew this was obviously Wayne’s only shot at the title. O’Toole’s next nomination, in 1973, would put him up against Marlon Brando in “The Godfather,” so fuhgeddaboudit — but he was still in his early 40s and would surely have more chances …
The problem is that, left with too many years of inaction, the academy sometimes lets beloved movie stars die empty-handed (poor seven-time nominee Richard Burton, another of the generational talents blocked by Wayne) — or worse, panics, and rewards them for regrettable performances.
More than 30 years later, there are still a lot of bad feelings out there about Al Pacino — with his hammy scenery-chewing as a blind, short-tempered retired lieutenant colonel in “Scent of a Woman” (1992) — besting Denzel Washington’s career-defining performance in “Malcolm X.” But Pacino — who had previously racked up seven nonwinning nominations in both lead and supporting actor categories — had the misfortune to be born into the talent-packed generation of actors who would redefine cinema in the 1970s, when he would be destined to lose to top-of-their-game peers like Dustin Hoffman and Jack Nicholson as well as overdue old guys like Jack Lemmon and Art Carney.
Sometimes, it must seem like you’ll never come off the Oscar waiting list. Observe Paul Newman’s expression, a wry smirk beating back the faint sparkle of anticipation in his eyes when the camera turned to him as his name was called among the 1983 nominees. He had already lost for all his most iconic roles to date — “Cat on a Hot Tin Roof” (it was screen veteran David Niven’s turn), “The Hustler,” (to his exciting new contemporary Maximilian Schell), “Hud” (when Sidney Poitier would become the first Black man to win the prize), “Cool Hand Luke” (it was Rod Steiger’s year).
You could just imagine his inner monologue: He hadn’t wanted to go, but probably Joanne Woodward convinced him. Sure, “Gandhi’s” the big movie this year, but they don’t even really know Ben Kingsley, and they LOVE you! Maybe she was right? Henry Fonda had finally won for the first time a year earlier — an old man playing an old man in the sentimental “On Golden Pond” — and promptly died a few months later at the age of 77. Maybe that’s how it works?
But by this point in the night, “Gandhi’s” rapid accumulation of smaller Oscars had made it clear which way things were going (Newman’s “The Verdict,” a highly rewatchable masterpiece, won zero), and now he was stuck: committed to the monkey suit, the center-aisle seat, and of course he was going to lose, again. And he did.
Four years later, finally, it really was Newman’s turn, for showering his charisma onto a middling Martin Scorsese movie, “The Color of Money.” But when they panned to the audience, Newman wasn’t there. The director Robert Wise, then the academy’s president, accepted on the star’s behalf.
“I talked to him this morning,” Wise told reporters after the show. “And he said after having been out here seven years previously, seven times, he felt that coming here again was almost a form of cruel and unusual punishment. He claimed a kind of constitutional protection, and he said, ‘I think people will understand.’”
Happily, no young actor more deserving got crowded out by Newman’s win that year. But it happens, and it will happen again. The ever-boyish Matt Damon is 55 and still hasn’t won an acting Oscar. Same for Edward Norton, already 56. Before you know it, they’ll be the age that Wayne was when he got his “overdue” Oscar or Martin Landau when he won for supporting actor, edging out Samuel L. Jackson, who is now 77 and still without a competitive Oscar.
O’Toole grudgingly but graciously accepted his career-achievement Oscar in 2003, after the organization reminded him that other actors — including Newman — had gone on to win competitive Oscars after honorary ones. And sure enough, O’Toole did get another nomination, four years later for a quirky little British film called “Venus.” But that would be the same year Forest Whitaker would unleash his volcanic performance as Idi Amin in “The Last King of Scotland.” And the 74-year-old O’Toole was left in his seat, clapping for Whitaker with a blank stare. He died in 2013 at age 81.
In fairness, sometimes we can’t see it until it’s too late. We always think there will be so many more chances. Who knew at the time that “Pulp Fiction,” way back in 1994, was Peak Samuel L. Jackson? That was his moment to win, just as “Lawrence of Arabia” was Baby Peter O’Toole’s — the Timmy C. of his day, so fine-boned and exotic with those piercing blue eyes.
We regret to inform the academy that you have probably already missed your chance with Chalamet. You should have given him the prize for the Dylan biopic, surely a role even more challenging than Mahatma Gandhi. That was his moment.
It surely won’t be his moment 40 years from now, at an Academy Awards long since merged with the Emmys, the Grammys and the Nobel Peace Prize, bought by the Saudis and renamed “the Ivankas.” Then it will be Chalamet sitting hollow-cheeked and glassy-eyed in the audience, clapping wanly as someone not yet born swoops in on his last possible shot at the prize.
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