When Should Peter O'Toole Have Won His Oscar? An Investigation

(Welcome to Did They Get It Right?, a series where we take a look at an Oscars category from yesteryear and examine whether the Academy's winner stands the test of time.)

Last week, I went through the eight Academy Award nominations of Glenn Close to examine why the renowned actor has yet to win even a single Oscar in her career. She holds the record for the actor with the most nominations in history without winning, but she doesn't hold that record alone. She shares it with someone I think is safe to call a legend: Peter O'Toole. The British thespian of stage and screen who became an instantaneous movie star in 1962 with the release of "Lawrence of Arabia" was also nominated eight times over the course of his career and never won, and because he died back in 2013, the chance to win is obviously gone, whereas Close still could.

44 years elapsed between O'Toole's first and last Oscar nominations, all of which were for Best Actor. To be able to sustain a career of leading roles for that long is rather astounding. Four years before his final nomination, the Academy gave O'Toole a Lifetime Achievement Award, but that doesn't make up for the lack of a competitive win, though I'm sure they saw it that way. How did the Academy neglect to award one of the medium's finest actors? Was he, like Glenn Close, always a victim of circumstance, or did the Academy just consistently drop the ball when it came to Peter O'Toole?

T.E. Lawrence may not have technically been Peter O'Toole's first film role, but it was the first time a film rested on his shoulders. And what a film it is. To this day, "Lawrence of Arabia" remains one of the most staggering cinematic achievements in the history of the medium, but for as grand as David Lean's scope is, the complexity of its central character is equally as dazzling as the Ultra Panavision 70mm photography. The film took home seven Academy Awards that year, including Best Picture and Best Director, but O'Toole was not fortunate enough to win for what any person would claim to be his signature performance.

People in the Academy love making actors wait before the take home Oscars. There's this belief that winning one is a career achievement and not based on performance, though there are plenty of instances where the two align. This year was one of those years, as he lost to Gregory Peck for playing Atticus Finch in "To Kill a Mockingbird." Not only had Peck been one of the premiere leading men in Hollywood for two decades by that point, but he tackled one of the most famous characters in American literature with poise, grace, and presence, and the result ended up being his signature performance. Having two all-timers like that going up against each other is tough, but the Academy is always going to go for the veteran in that situation. The other three nominees were Burt Lancaster, Jack Lemmon, and Marcello Mastroianni, which makes for a murderer's row of a category, but this was ultimately a two-man race. While history would like to give O'Toole his Oscar for "Lawrence of Arabia," that would mean taking away Peck's. Nobody wants to do that. A heartbreaker year no matter what. 

Immediately after "Lawrence of Arabia," Peter O'Toole went from respected British stage actor to a prestige Hollywood leading man. His very next film was the slightly less massive period drama "Becket," an adaptation of Jean Anouith's 1959 play. The film stars Richard Burton as the titular Thomas Becket and chronicles his friendship and falling out with O'Toole's King Henry II. Whereas T.E. Lawrence is an incredibly internal performance, reliant on subtle shifts in those piercing blue eyes of his, Henry II in "Becket" is about as external as you can get. Playing the king as a spurned lover, he's a whirlwind of passion and debauchery, transforming every room he enters into a show starring him that perfectly complements the far more stoic and reserved Burton.

Once again, he was up against a veteran actor giving what we think of as his signature performance. In this case, that would be Rex Harrison as the abrasive, persnickety phoneticist Professor Henry Higgins in "My Fair Lady," which also won Best Picture and Director. What I like about this win is the Academy actually went for comedy. Yes, "My Fair Lady" is an opulent musical extravaganza, but it is still a romantic comedy. His other prime competitor came from another comedy: Peter Sellers in his trio of roles in "Dr. Strangelove." O'Toole did take home the Golden Globe for Best Actor in a Drama, but I'm not so sure that was indicative of his ability to topple Harrison.

This was O'Toole getting nominated for two films in a row, which showed that he had a staying power and wasn't some flash-in-the-pan phenomenon. Like his fellow eight-timer Glenn Close, I think the idea that he would eventually win became a prevailing notion, and he would start getting put on the back burner.

It took four more years until Peter O'Toole received his next Oscar nomination, after having some fun in films like the deliriously lovely caper "How to Steal a Million" with Audrey Hepburn. Guess what? It was for playing King Henry II in a film adaptation of a stage play again, though not a sequel to "Becket." This was for "The Lion in Winter," which was not just a lavish period drama but also a massive hit. It's also one of those stage adaptations where every single line is an absolutely delicious. While O'Toole obviously didn't take home the award (otherwise this piece doesn't make sense), his co-star Katharine Hepburn did win Best Actress for her performance, which was remarkably a tie with Barbra Streisand's breakout work in "Funny Girl."

Taking all of his nominations into account, I think "The Lion in Winter" was O'Toole's best shot at winning. It's the only time (with one other exception we'll get to) that he wasn't up against a complete juggernaut of an opponent. The winner that year was Cliff Robertson for the film "Charly," which not only is a movie that has aged like milk due to its depiction of a neurodivergent man, but was a controversial win at the time. Before Robertson, doing heavy campaigning for awards was far more unusual, but he really went for it. Press coverage directly following the win immediately chalked up the result to the glad handing than the work. He also was the only nominee for "Charly."

O'Toole did win the Golden Globe for Best Actor in a Drama over Robertson, which does show there was at least some support out there for him, and perhaps if he played the game as well, he could've gotten that Oscar too.

Four his next four nominations, Peter O'Toole was in the unfortunate situation of competing against some of cinema's biggest icons and always drew the short straw. The year after "The Lion in Winter," he gets his fourth nomination for a musical adaptation of "Goodbye, Mr. Chips." Notably, this lead role already produced an Oscar winner for Best Actor back in 1939 when Robert Donat took on the role, beating out the likes of James Stewart in "Mr. Smith Goes to Washington," Clark Gable in "Gone with the Wind," and Laurence Olivier in "Wuthering Heights." Where that original film got nominations across the board that year, this musical version only was recognized for O'Toole and the original score.

So, who was this heavyweight that he lost to? Oh, just John Wayne winning his only Academy Award for his performance in "True Grit." At that point, Wayne had arguably been Hollywood's biggest leading man for 30 years, but because of his well-curated movie star persona, he never got much of a shot at awards, only being nominated once for acting prior to "True Grit." This was Wayne taking that bravado that made him such a star and channelling it into someone who was a has-been that needed to prove himself to the world again. It's the kind of narrative and performance the Academy simply cannot resist. And if there wasn't John Wayne to contend with, O'Toole would still have had to face off against the two stars of the Best Picture winner that year, "Midnight Cowboy." No, this year was not going to be his year however you slice it.

If you thought John Wayne in "True Grit" was a formidable opponent, you ain't seen nothing yet. Peter O'Toole in "The Ruling Class" was the first time in his career that he was the sole representative of his film at the Oscars. This was a time where the New Hollywood was in full swing, and a strange, mildly accepted black comedy from England was not exactly the toast of the town, no matter how good it was. In the Best Actress category, not having across-the-board support for the film is far more common, as there is an undeniable misogyny throughout the Academy. In Best Actor, not having the broad recognition certainly diminishes your chance of winning.

The year "The Ruling Class" was released was 1972, and for those of you who know history, you know this is the year of "Cabaret" and "The Godfather," which means that Marlon Brando won the Best Actor trophy that year for his work as Don Vito Corleone. If you were to make a list of the most iconic film performances and characters of all time, few people would object to it being in the top five, if not number one. You go up against a force like that, and you are going to lose. They even decided to have Al Pacino run in Best Supporting Actor because they knew he'd lose to Brando (I don't think they predicted him losing to Joel Grey). Sole nominee Peter O'Toole in a comedy can't compete with that.

It would be another eight years until Peter O'Toole received another Oscar nomination, the longest stretch between them so far due in part to many alcohol-related medical issues. "The Stunt Man" probably has the smallest cultural footprint of them all his nominated films. He doesn't play the titular stunt man. That would be Steve Railsback. O'Toole plays a film director who employs this man-on-the run as a stunt performer to replace one who died during production by driving a car off of a cliff. He is the stunt man's best friend and worst enemy all at once. Though he is far and away the biggest name in the cast, I wouldn't exactly call him the lead of the picture. I actually think you could have made the case to run him in Best Supporting Actor and probably had a better shot at winning, though O'Toole did win the Best Actor prize from the National Society of Film Critics.

That was the only notable award he did take home that year though because his competition just so happened to be another all-timer performance. The person who took home every other award that season was Robert De Niro for his work in Martin Scorsese's boxing film masterpiece "Raging Bull." Though it isn't as titanic in terms of the canon as Marlon Brando in "The Godfather" (what is?), it's pretty close. This is the culmination of all the transformative, daring work De Niro was doing in the 1970s, and in a career filled with some of the best performances of all time, this very well might be his crowning achievement. "The Stunt Man" did get a little more love from the Academy, with Best Director and Adapted Screenplay nominations, but O'Toole was always a long shot here.

"My Favorite Year," once again, saw Peter O'Toole as the only representative for the film at the Oscars that year, and like "The Stunt Man," he isn't really the protagonist of the story but the colorful wild card who can throw everything into chaos. The film is loosely inspired by Mel Brooks' time as a writer on Sid Caesar's "Your Show of Shows," with Mark Linn-Baker playing the Brooks analogue Benjy Stone. O'Toole plays a past-his-prime actor, in the vein of Errol Flynn, making a guest appearance on the sketch show and causing an absolute ruckus. It is a big, funny performance from O'Toole, which is not exactly the way into the hearts of Oscar voters.

I have written extensively about the 1983 Academy Awards before and the dominance of "Gandhi." Well, the trickled over into the Best Actor category too with Ben Kingsley winning for the titular role. Yet another time he loses to someone giving the performance you most associate with that actor. The Best Actor category that year was incredibly formidable, and "My Favorite Year" is the only film represented there that didn't also receive a Best Picture nomination, which leads me to believe that O'Toole was firmly running in fifth place that year.

By this point, O'Toole had seven nominations under his belt in 20 years and was clearly overdue to win. I think if he had delivered some kind of thumping, loud performance within the next few years that he could have won. But that didn't happen. He swerved entirely into the silly with films like "Supergirl," "Creator," and "Club Paradise." It had been quite awhile since he had made a serious minded prestige film, and the urgency to award him faded away.

Peter O'Toole wouldn't receive another Oscar nomination for 24 years. He had gone so long without one that the Academy gave him a Lifetime Achievement Award four years before the release of "Venus," which marked his eighth and final time in competition. Next to "The Lion in Winter," the circumstances for O'Toole to win this were perfectly set up. The Academy has no qualms about awarding a long overdue elder statesman for a quiet, contemplative drama. Helen Mirren did it this very same year for "The Queen," though she had the benefit of portraying one of the most famous people in the world. The Academy may like giving career Oscars, but they love awarding biopics just a little bit more.

This was the third year in a row that Best Actor had gone to a big biopic performance. In this case, that would be Forest Whitaker for "The Last King of Scotland." I love that Whitaker has an Oscar. He is the consummate character actor and rarely given the opportunity to be the lead of the film. He's also one of the very few Black actors to ever win this award. That being said, like so many biopics, the lasting legacy is the historical stat of the Oscar win and not the quality of the film. Whitaker steamrolled the awards that year, but when was the last time you thought about "The Last King of Scotland"? As a whole, that year's Best Actor category leaves a lot to be desired. It's filled with five wonderful actors, but none are delivering their best work. Had the allure of the biopic not been there, I think this would have been an award that was gettable for Peter O'Toole. Unfortunately, it was his last chance.

If you are someone who still believes that the Academy Awards are a meritocracy, I am sorry to say that this is nowhere near the truth. So many stars need to align in order for someone's name to be pulled out of the envelope. It needs to be the right performance in the right role in the right year with the right competition with the right campaign strategy. Peter O'Toole may have had a whopping eight at-bats for those stars to align, but they never did. In every instance, the stars were better suited to help someone else than him.

I think it's a shame. Peter O'Toole was a true force of nature on screen and should have been recognized for being that force. Luckily, the Academy did at least give him an honorary award, which is more than you can say for a lot of folks. When they did that, they obviously knew the history of him not winning would look rather poorly, and it does. While I think he should have won for "The Lion in Winter," I fully understand how he always ended up empty handed. There isn't an instance where his loss is completely inexplicable. That doesn't make the results any less disappointing.