The Winner Changes All: Best Supporting Actor, 1944

Presenting the 17th Academy Awards' nominees for Best Supporting Actor:

Hume Cronyn, The Seventh Cross

Barry Fitzgerald, Going My Way

Claude Rains, Mr. Skeffington

Clifton Webb, Laura

Monty Woolley, Since You Went Away

Cronyn is a man in Nazi Germany who must choose between protecting himself and helping a friend, a political refugee. Fitzgerald is an old and old-fashioned priest with a crumbling parish. Rains is a successful Jewish businessman who marries a woman who loves his money more than him, but he's hopeful that'll change. Webb is a bitchy columnist whose protege's murder is investigated. Woolley is a stuffy retired colonel boarding with a middle-class family, nursing a strained relationship with his grandson.

This was always going to be Fitzgerald's Oscar:

The fact that he was nominated for the exact same performance in Best Actor tells you so. At the time, Academy bylaws permitted an actor to be considered for whatever category, and he happened to score enough votes to place in both categories. Afterward, rules were changed so that an actor could only be nominated in the category submitted by their studio, but that got confusing, too: a clerical error in 1963 led to the entire cast of Cleopatra being submitted as leads, while Peter Sellers' multiple roles in 1964's Dr. Strangelove led to four simultaneous campaigns: one in Lead for all three roles together, and three in Supporting for each role individually. So then the rules were changed again: you could vote for a role in whichever category, but the category they got the most votes in first would be their nomination: thus, Kate Winslet in The Reader went from being campaigned all 2008 as Best Supporting Actress, only to wind up in Best Lead Actress.

So that's how a Supporting Actor won the Oscar and changed the rules.

It's not, admittedly, the best lineup. My rankings, from fifth to first:

The Crooner Crowned: Best Actor, 1944

Presenting the 17th Academy Awards' nominees for Best Actor in a Leading Role:

Charles Boyer, Gaslight

Bing Crosby, Going My Way

Barry Fitzgerald, Going My Way

Cary Grant, None But the Lonely Heart

Alexander Knox, Wilson

Boyer is a villain, mentally torturing his wife for reasons to be revealed. Crosby is a chill, hands-in-pockets priest come to shake things up at a crumbling parish. Fitzgerald is the old and old-fashioned priest who runs that parish, and has done so for a long time, perhaps too long. Grant is a Cockney who can't help getting into trouble. And Knox is the President of the United States who spearheaded the establishment of the League of Nations.

There were fewer "precursors" at this time, and the ones from that period that still remain were not as we know them. Knox and Fitzgerald won the Golden Globes for Lead and Supporting Actor, respectively, but at that time, there were no nominees, only winners - and no distinction between Drama and Musical/Comedy. Fitzgerald was named Best Actor by the New York Film Critics Circle, but that organization did not even introduce Supporting prizes until 1969. And Crosby's performance was cited by the National Board of Review for Best Acting...alongside eight others, male and female, lead and supporting (among the names: Eddie Bracken in Hail the Conquering Hero and Humphrey Bogart in To Have and Have Not, which was eligible for the next year's Oscars). 

Crosby himself claimed he did not expect to win, that Knox would be unbeatable. Indeed, he had to coaxed off the golf course by studio publicity people and his mother just two hours before the ceremony started - which explains the hat in photos from that night, hiding his toupee-less scalp. It's a good thing he went, because it meant Gary Cooper didn't have to present the Oscar to nobody.

Yes, despite his own doubts (or insecurities?), Crosby won, and he'd even be back the very next year for the very same role. Would he get my vote? Read on: