Say you are an extremely famous and/or wealthy person, and you decide you would like to have an Oscar. You could have just bought the Oscar that cinematographer Clyde De Vinna won at the second ceremony ever when it was auctioned earlier this year, but maybe you were busy that month. Or maybe what you want, more than anything, is to win a competitive Oscar, despite not being primarily known to this point for your film career.
Now imagine that you are a specific extremely famous and/or wealthy person. Imagine you are Taylor Swift, acclaimed pop star, celebrated songwriter, and director of All Too Well: The Short Film. And if you want to win an Oscar, those two words “short film” are your ticket to the stars. Increasingly, the live-action and animated short film categories are ways for famous people to win Oscars in far less competitive categories.
The Oscars are famously one of the more difficult competitive awards to win, but there are categories that are … less contested, let’s say, and categories where the rules to qualify are less stringent than in others. If you have access to the resources required to first get a film to qualify and then to mount a campaign for it to be nominated and eventually win — well, you’ll have a real leg up over the other nominees in a historically under-the-radar category.
As such, it makes sense for you, Taylor Swift, to mount an Oscar run in the live-action short category for your 15-minute, music-video-adjacent expansion of your 10-minute song expansion of your already pretty perfect five-and-a-half minute song “All Too Well.” (More on the relationships between all of that here.)
You aren’t breaking new ground here. You are following in a tradition several decades old, one that has benefited everyone from Kobe Bryant to Christine Lahti. You’re just arguably the most famous person to ever tread this path, and as such, you’re probably going to draw a lot more attention to this occasionally traveled Academy Awards byway.
How to win an Academy Award for your short film
The Academy Awards for animated and live-action short film have long been afterthoughts in the endless Oscar ceremony. Short films used to be shown before the main feature, back in the days when you would go to a movie theater for an evening’s entertainment that would often feature, among other things, a cartoon, a newsreel, a short, and at least one feature film. Now they exist primarily as a way for interesting young writers and directors to create calling cards that will get them noticed in the industry.
Sometimes, those promising young writers and directors create something that garners so much notice it launches their career and wins them a major prize. Directors like Taylor Hackford (Ray), Andrea Arnold (American Honey), and Martin McDonagh (Three Billboards Outside Ebbing, Missouri) won Oscars for live-action short film — Oscars that helped launch their…