“Always a bridesmaid, never a bride – my foot!” said Peter O’Toole, somewhat mischievously, as he accepted his Honorary Oscar from Meryl Streep at the 2002 Academy Awards. “I have my very own Oscar now to be with me until death us do part.”

 It was a speech of twinkly good grace from the Irish actor, then 70 years old – seasoned enough, in other words, to know that an Oscar is nice and all, but not so important that it can’t be left behind at the pearly gates. But it was also delivered with a kind of good-humored resignation. O’Toole may have been several years off retirement – and there was one more near-brush with victory still in his future -- but he seemed to know he’d never win a competitive Oscar. More to the point, he seemed to know there was nothing more to be gained from winning one, if indeed there ever had been. O’Toole’s charm, on screen and off, so often lay in being the guy just outside the inner circle.

His “always the bridesmaid” quip wasn’t an idle one – it was a wry nod to Oscar statisticians and gatekeepers. At that point, O’Toole had gone zero-for-seven in the Best Actor category, sharing the record among actors for most nominations without winning with his near-contemporary Richard Burton.

He’d claim the record for himself four years later, after an eighth unsuccessful Best Actor bid for the dying-of-the-light drama “Venus,” but it felt oddly appropriate that Burton and O’Toole should have jointly held that distinction for 20-plus years – and not only because O’Toole’s second nod and Burton’s third came for the same film, 1964’s thespian showdown “Becket.” Both men were unapologetic industry outsiders: one Welsh, one Irish, both charismatic, imposing, hard-living talents, too self-evidently gifted for the Academy to ignore, yet too spiky for them to unreservedly embrace.

Oddly, O’Toole could so easily have been let off the hook his very first time at bat. Few Best Actor runners-up can count themselves as unlucky as O’Toole in “Lawrence of Arabia,” just as few actors have ever been handed quite such a meaty opportunity for their first starring role. His performance as the prodigious British Army officer T.E. Lawrence in David Lean’s landmark epic was one hell of a near-debut, marrying theater-schooled technical might with incalculable movie-star quality – it may have been a biopic, but the performance also locked down the brilliant misfit screen persona that would see O’Toole through his entire career.

In any other year, O’Toole would probably have won Best Actor, adding another Oscar to the Best Picture winner’s dominant tally of seven. But in any other year, he wouldn’t have been up against Gregory Peck in “To Kill a Mockingbird” – a well-liked, well-established five-time nominee awaiting his first win, and securing it with a performance of differently-scaled detail and dignity as liberal lawyer Atticus Finch in “To Kill a Mockingbird.” It’s hard to take issue with the Academy’s decision on aesthetic grounds, or on theoretical ones: O’Toole was only 30 (had he won, he’d have been the youngest Best Actor victor to date), and voters could be forgiven for thinking his day would come.

It didn’t, of course, though not for lack of opportunity. Two years later came “Becket,” in which O’Toole and Burton – as, respectively, the callow King Henry II and Archbishop of Canterbury Thomas Becket – both delivered the kind of high-toned, elegantly articulated performances for which Academy voters routinely hold UK and Irish actors in such high regard. Either man alone might have been a threat to fellow Brit Rex Harrison’s droll musical turn in “My Fair Lady”; together, each consumed too many of the other’s vote. No matter. There’d be other chances, right?

There would indeed – and other chances playing Henry II, to boot. Four years later, O’Toole was back in the nominees’ circle for “The Lion in Winter,” a more weathered (O’Toole was 35, playing 50) but even more magnetic incarnation of the blustery royal, with a formidable Katharine Hepburn as his Eleanor of Aquitaine – it’s a testament to both performances that the film doesn’t feel nearly as much a clash of thespian generations and movements as it actually is.

Hepburn won Best Actress, and O’Toole looked primed for a matching award, particularly given the opposition. Ron Moody, Alan Arkin and Alan Bates were fine but resistible competitors, and while Hollywood workshorse Cliff Robertson stepped up his game as a mentally handicapped victim of science in the “Flowers for Algernon” adaptation “Charly,” surely the Academy wouldn’t feel he need an Os—nope, they did, as Robertson unusually struck gold at his first and only nomination, for a film ignored in every other category.

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Guy Lodge is a South African-born critic and sometime screenwriter. In addition to his work at In Contention, he is a freelance contributor to Variety, Time Out, Empire and The Guardian. He lives well beyond his means in London.