Cary Grant never won an Academy Award for acting. Neither did Edward G. Robinson or Barbara Stanwyck or Deborah Kerr, despite her six nominations, or Peter O’Toole despite his eight. The list goes on and on. The Academy of Motion Picture Arts and Sciences tried to make up for such slights by giving everyone an Honorary Oscar, just as it did with never-even-nominated Maureen O’Hara, who was an honoree at this year’s Governors Awards. It’s a familiar story—some Hollywood greats are just star-crossed when it comes to Oscar. But the bottom line of winning isn’t necessarily because someone should or is overdue or deserves it. It’s all about the role . . . and catching the zeitgeist.

On the other hand, Ernest Borgnine, F. Murray Abraham, Cliff Robertson, Haing S. Ngor, Harold Russell, Jean Dujardin, Mo’nique, Roberto Benigni, Cuba Gooding Jr., Tatum O’Neal, Marlee Matlin and Linda Hunt—all the way up to last year’s supporting actress winner Lupita Nyong’o—managed to win an Oscar on just their first and only nomination. They did it with the role of a lifetime, not necessarily a lifetime of achievement or plain ol’ stardom. Oscar is funny that way.

2009 Oscar Best Actor
Robert Downey Jr.’s uber-Method Kirk Lazarus in the showbiz satire Tropic Thunder offered hilarious insight into how certain types of roles resonate with the Academy. Ironically, Downey Jr. received a supporting actor nom for the comedic part, ultimately losing in 2009 to Heath Ledger, who won posthumously for what turned out to be a once-in-a-too-short-lifetime performance as the Joker in The Dark Knight.

Albert Finney, like O’Toole and Richard Burton — who led the list of Oscar’s most losing-est actors — was, and remains, way overdue for a golden guy. Finney should have won his first time out in 1963 for that year’s best picture winner, Tom Jones, but he lost to Sidney Poitier, who had his role of a lifetime in Lilies of the Field but hasn’t been nominated since. Finney might have grabbed the Oscar in 1974 for Murder on the Orient Express, but TV second-banana Art Carney got his role of a lifetime in Harry & Tonto and took the Oscar instead. Or even in 1984, when Finney was so brilliant in Under The Volcano. Instead, the award went to stage actor F. Murray Abraham, another one-time nominee, for his Salieri in Amadeus.

Burton should have won the Academy Award for Who’s Afraid of Virginia Woolf? in 1966, but he had the misfortune of losing to first-time nominee Paul Scofield, an English theater star who rode the wave of playing Sir Thomas More in that year’s best picture winner, A Man for All Seasons. O’Toole almost certainly would have won on his first time out for 1962 best picture winner Lawrence of Arabia, but how do you deny Gregory Peck—who won with his role of a lifetime in To Kill a Mockingbird? (The nod turned out to be Peck’s final nomination.)

Annette Bening is another thesp who is long overdue. She’s had four nominations and managed to lose every time—twice to Hilary Swank, who has gone two-for-two for the uniquely twice-in-a-lifetime roles in Boys Don’t Cry and Million Dollar Baby. Again, Oscar doesn’t seem to care if you already won and are up against a deserving nominee who has never won.

It looked as if Paul Newman was never going to win after his six best actor losses. The Academy gave him an Honorary Award in 1985, just one year before he won on his own accord for reprising his 1961 Oscar-nominated Hustler role of Fast Eddie Felson in The Color of Money. I actually think he should have won the first time he played Felson, but Maximilian Schell in Judgment at Nuremberg took that win on his first try. Glenn Close is now up to six nominations with no Oscar to show for it, losing in 2011 (for Albert Nobbs) to three-time winner Meryl Streep for The Iron Lady. The score is now Streep: 3, Close: 0. We can go on all day with this stuff.

But looking at this year, who has got the Oscar role? That has to be Eddie Redmayne, poised to win his first nomination, and possibly Oscar, for playing the ALS-stricken Stephen Hawking. It’s not like the young thesp is owed anything. He’s just riding the right horse. Veteran Michael Keaton looks likely to grab his first nomination in a long career for Birdman, but Redmayne probably has the role. Interestingly, another top contender is Benedict Cumberbatch for The Imitation Game, but he also once played Hawking on British television. If he had done the movie version instead, the tables would be turned. David Oyelowo was so certain that playing Martin Luther King Jr. in Selma would be the role for him that he tried for seven years just to get the film made, and now has joined the Oscar conversation. Julianne Moore has had four previous nominations; playing a woman suffering from Alzheimer’s in Still Alice suddenly has made her the lead actress front-runner this year. A lot of that heat has to do with, you guessed it, the role.

The same rules apply to just about every category in the Academy. Steven Price won on his first score nomination for Gravity. The multi-nominated Alex North and Ennio Morricone never won Oscars, so the Academy had to give them honorary ones out of embarrassment. Like I’ve said, it’s not always fair. But hey, that’s Oscar.