Mastermind
That's a Real F*cking Legacy
No, It's Becky
She's an Actress, Woah
I Got Some Big Enemies
100

The 2019 music video for "ME!" featured a neon sign of this word, later revealed to be the title of her upcoming album

What is "Lover"?

100

Swift received this Time Magazine award in December 2023

What is Person of the Year?

100

This Taylor Swift song has a well known remix that features a goat

What is "I Knew You Were Trouble"?

100

In preparation for her role of Bombalurina in this movie, Swift attended “Cat School” classes

What is "Cats"?

100

This rapper interrupted Swift's acceptance speech in 2009 promising to "let her finish"

Who is Kanye West?

200

In the music video for "Look What You Made Me Do", dancers wore a shirt featuring this phrase, a nod to her short lived relationship with Tom Hiddleston

What is "I <3 TS"?

200
In 2009, at 20 years old, Swift became the youngest artist in history to win this award

What is the Grammy for Album of the Year?

200

At a 2023 concert in Glendale, AZ, Swift dispelled the long running rumors that she disliked this album

What is "Evermore"?

200

In the movie "Amsterdam", Swift's character dies rather swiftly in this manner

What is getting pushed into oncoming traffic?

200

Swift's 2015 single "Bad Blood" is rumored to be about a feud with this fellow pop star

Who is Katy Perry?

300

Swift teased the opening song of her Eras Tour by posting this phrase on an Instagram post announcing the tour

What is "It's been a long time coming"?

300

In 2023, Swift turned the Eras Tour into a concert movie in an untraditional way by bypassing studios and going straight to this distributor

What is AMC Entertainment?

300

This 2023 event prompted many Taylor Swift fans to post "I survived the Great War" on social media

What is Ticketmaster crashing?

300

Swift's acting role in this movie marked the birth of a phenomenon known as “Taylor Squared"

What is "Valentine's Day"?

300

Going against her wishes, this famous manager purchased Swift's masters for $330 million in 2019

Who is Scooter Braun?

400

In a February 2021 Instagram post, Swift announced the release date of "Fearless (Taylor's Version)" by doing this

What is capitalizing letters that spelled out APRIL NINTH?

400

In November 2023, Brazil welcomed Swift ahead of her concerts in Rio de Janeiro by displaying this article of clothing on the Christ the Redeemer statue

What is the the Junior Jewels tshirt?

400

A meme was born when a troll post on Tumblr posted an old photo of Taylor but claimed it was their friend Becky, who died for this reason in middle school

What is a marijuana overdose?

400

Swift portrayed rebellious teenager Haley Jones in season nine of this drama series 

What is CSI?

400

This model and Swift are rumored to have had a falling out, as they were last spotted together at a Reputation concert in 2018

Who is Karlie Kloss?

500

In her acceptance speech at the 2020 AMAs, Swift teased the release of her upcoming album "Evermore" by doing this

What is showing the back of her head?

500

In October 2022, Swift became the only artist in history to achieve this feat on the Billboard Hot 100

What is claiming all top 10 entries in a single week?

500

This phrase was often posted online by fans in response to Swift appearing in a suggestive or beautiful outfit in a public outing

What is "Joe Alwyn, can you fight"?

500

Swift made a cameo in this TV show, where she acts out the situation described in the title track of her third album

What is "New Girl"?

500

He is rumored to be the inspiration behind the following lyrics:

"I didn't have it in myself to go with grace
'Cause when I'd fight, you used to tell me I was brave"

Who is Scott Borchetta?