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 feature-film directing careers.

The short film categories are unusually susceptible to interlopers, however, because they play by their own set of rules. Most categories at the Oscars require a movie to screen for a week in theaters in LA, New York, Chicago, the Bay Area, Atlanta, or Miami to be eligible. But the short film categories offer three different paths to Oscar glory, since so few short films are screened in American theaters anymore. Those three paths are:

• Screen your short film in a theater in Los Angeles, New York, Chicago, the Bay Area, Miami, or Atlanta for at least one showing per day for one week. The public has to be able to buy tickets to those screenings, and at least one of those screenings has to precede the release of your short film in a medium other than a movie theater, such as television or streaming. This path is similar to most other Oscar categories’.
• Win an award for your short film at a film festival the Academy has deemed worthy of qualifying you for a run at an Oscar. The list of eligible film festivals is 14 pages long and includes everything from winning the Palme d’Or for short film at the Cannes Film Festival, the most prestigious in the world, to winning the “Golden Starfish Award for Best Short Film” at the Hamptons International Film Festival. You have options!
• If you’re a film student, you can qualify by having your film win a Gold, Silver, or Bronze prize in the Academy’s Student Academy Awards.

For her part, Taylor Swift (sorry, you’re not her anymore, unless you literally are, in which case, hi) screened All Too Well: The Short Film for one week at the AMC Lincoln Square in New York last November. While that timing would qualify her for the 2021 Oscars in most other categories, which run on a January 1 to December 31 qualifying calendar, the short film categories follow the festival calendar more closely and run on an October 1 to September 30 calendar. Therefore, a short film from November 2021 is eligible for the 2022 Oscars.

Swift took the short to the Tribeca Festival in June, and she will also screen it at the Toronto International Film Festival, complete with a Friday, September 9, conversation with the festival’s CEO, Cameron Bailey.

The Tribeca and TIFF appearances aren’t really for Oscar-qualifying purposes as much as they’re designed to keep the film in the public eye (since TIFF is one of the major Oscar precursor festivals) and to establish Swift’s bona fides as a director. A Tribeca conversation with filmmaker Mike Mills dug into Swift’s filmmaking influences, her potential desire to direct a feature someday, and her increasing ability to step outside of her songwriting comfort zone.

It is worth noting here that Taylor Swift is extremely rich and famous. She can afford to not only make a short film, but also book a movie theater to screen it at a time when most theaters aren’t making a habit of showing short films. That’s a path not every filmmaker can take, and it gives her an advantage in a category that historically favors up-and-coming directors. That said, Swift is technically an up-and-coming director, one whose short film bears a sophisticated visual eye while also falling prey to the common young director pitfall of moving the camera way, way too much.

Finally, Swift is Oscar-eligible in a different category this year, one where you’d more likely predict her to be nominated: Best Original Song. “Carolina,” a song she wrote for the film Where the Crawdads Sing, will be eligible for that category. Whether “Carolina” will be nominated or suffer the same fate as her non-nominated song from Cats remains to be seen. She’s also in the movie Amsterdam, from Oscar-favorite director David O. Russell, but that’s a small supporting part and unlikely to garner awards attention.

Taylor Swift might be the most notable famous person to use the different rules of the short-film category as a sneak attack on the Oscars, but she’s far from the only one. She’s not even the only famous person to attempt an Oscar run like this in this year.

Why did Kobe Bryant win an Oscar? He made a short film.

In 2018, basketball legend Kobe Bryant won an Oscar for animated short film for the film Dear Basketball. Bryant was not an animator, and he did not direct the film. (Legendary animator Glen Keane handled that job, thus winning his own first Oscar.) Because the film was based on his script, however, Bryant shared in the prize. It was the first time many Oscar watchers became aware that, hey, a short-film Oscar seems to be much easier to win than an Oscar in a more competitive category.

The very next year, actress Jaime Ray Newman, best known for her work on TV, shared the live-action short film prize with director Guy Nattiv for the film Skin. Earlier this year, actor Riz Ahmed (previously an Oscar nominee for Best Actor for The Sound of Metal) won his own Oscar in the live-action short film category for The Long Goodbye, directed by co-winner Aneil Karia and based on Ahmed’s album.

Dig around in Oscar history and you’ll find all sorts of examples of the short-film categories’ relatively looser restrictions allowing interesting things to happen. Character actors like Christine Lahti and Ray McKinnon have won Oscars for shorts they directed and starred in, and the categories have also seen failed TV pilots and animated TV specials triumph. (The Academy quickly closed up the loopholes that allowed those wins to happen.)

This year, the recent prominence of Bryant and Ahmed’s wins has raised the profile of this path to Oscar glory, and other famous people are availing themselves of it. The Hollywood Reporter’s Scott Feinberg says that musician Kendrick Lamar’s short film We Cry Together screened for a week in Los Angeles in June and thus will be Oscar-eligible this year.

I want to be careful not to be too cynical here. All of the short films listed here stemmed from places more pure than simply longing to win an Oscar. Swift’s reclamation and reinvention of one of her most famous songs, Ahmed’s exploration of his fears around racism in Britain, Bryant’s ode to a sport he loved — they’re all best understood as artistic expressions first and awards plays second. Yet they are all awards plays, too. Why would any of these people go to the trouble of booking a theatrical run if not to qualify for an Oscar?

Which brings me to my final question: Do you think Taylor Swift cares if she EGOTs?

Do our celebrities feel the looming specter of the EGOT, or do they not care?

The EGOT — winning a competitive Emmy, Grammy, Oscar, and Tony — is one of those weird little bits of celebrity trivia that has slipped into the public consciousness. Though the term was invented by Miami Vice star Philip Michael Thomas, who stated it was his career ambition (he’s won none of the awards), it has taken off in the public consciousness. That’s thanks to some combination of 30 Rock, the way the internet makes it much easier to collect this sort of trivia, and how fun EGOT is to say.

Just 17 people have won an EGOT, with Jennifer Hudson joining the list in June, making her the most recent addition. Lots and lots of people have won two or three of the prizes; few have won all four. Even illustrious names like Stephen Sondheim and John Williams have only won three out of four. (Barack Obama, the only president to win more than one of these awards, has two out of four, thanks to a long-ago Grammy win and an Emmy win earlier this month. We can only hope he’s mounting a Tony-eligible revival of Urinetown even as we speak.)

Theo Wargo/Getty Images for Tony Awards Productions

Swift has an Emmy and a Grammy, but the Oscar and Tony are historically the trickiest of the four awards to win. What’s more, her rough contemporary Adele just added an Emmy to her Grammy and Oscar last Saturday, when her special Adele One Night Only picked up a prize for the best prerecorded special. When it comes to other woman pop stars of the moment, Billie Eilish has several Grammys and an Oscar, and one can only assume an Emmy will follow whenever she decides she wants to write a song for Euphoria or something. If we expand to include men making music at the moment, John Legend already has his EGOT. Swift is falling behind!

(A musician who doesn’t yet have the awards recognition you’d expect is Beyoncé, who has won several Grammys but lost her first Oscar nomination to Eilish earlier this year. She received two Emmy nominations for her stunning 2016 video album Lemonade, but she lost a directing bid to Grease Live! and the variety special prize to a Carpool Karaoke special. Icons are often not recognized by awards bodies until later on, but I’m going to go out on a limb and say Lemonade probably should have won an Emmy over fucking Carpool Karaoke.)

I’m just not sure how much these celebrities actually think about EGOTing. If a legend like Stephen Sondheim gave a shit about whether he won an Emmy Award, allowing him to EGOT before he died, he surely would have cranked out a theme song for some forgettable sitcom or something. Lots of famous people probably enjoy winning awards but don’t think as hard about whether they will EGOT as those of us who follow “the industry” might.

So does Swift spend all her time strategizing how to win an EGOT? God, I hope not. If I were Taylor Swift, I would think about lots of other things before I thought about getting added to the Wikipedia page “List of EGOT Winners.” I must admit, however, that if I had an Emmy and a Grammy, I would definitely think all the time about how to get the Oscar and Tony, so maybe I’m wrong.

Regardless of motives, regardless of intent, winning an Oscar would be a feather in anyone’s cap. If Taylor Swift is able to win the Oscar for live-action short film, it wouldn’t be the category you’d most expect her to win in, but it would be an Oscar. For the rest of us, Swift winning a short-film Oscar would make for a fun trivia question years down the line. So see? We all win!