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100

The Kentucky Derby takes place at this historic racetrack.

What is Churchill Downs?

100

This water sign, symbolized by the Scorpion, is often linked to intensity and transformation.

What is Scorpio?

100

Beginning with the day she was born in December, this number has become associated with many good things in the singers loge and is widely known as her favorite number.

What is 13?

100

This teen series, known for making one of the smallest no-name towns in Washington a popular travel destination in hopes of seeing something sparkle in the forest, was first released in 2005.

What is Twilight?

100

This traditional drink, made with bourbon, mint, and sugar, is famously served at the Kentucky Derby. You may be drinking one right now!

What is a Mint Julep?

200

This famous nickname refers to the Kentucky Derby due to its short duration and thrilling pace.

What is 'The Most Exciting Two Minutes in Sports'?

200

This zodiac sign is symbolized by the Ram and is the first sign of the zodiac.

What is Aries?

200

This world tour made over $2 Billion in ticket sales, and is Taylor Swift's largest tour to date.

What is the Eras Tour?

200

Welcome to Dead House from 1992 was the first of the books in the Goosebumps series by this author who by now has sold a spooky number of copies.

Who is R.L. Stine?

200

These small, chewy candies are bite-sized pieces of licorice often sold in movie theaters.

What are Nibs?

300

This is the age that all horses must be to compete in the Kentucky Derby.

What is three years old?

300

These three zodiac signs—Cancer, Scorpio, and Pisces—belong to this element, often associated with emotions and intuition.

What is Water?

300

Famous for dating two (and marrying one) women with the same name and him, this actor briefly dated Swift in 2009.

Who is Taylor Lautner?

300

2010's Easy A re-imagined this decidedly unfunny 1850 novel as a comedy.

What is the Scarlet Letter?

300

Whether called a cornichon or a gherkin, it's one of these vegetables at the start.

What are cucumbers? 

400

This horse, who won the 1973 Kentucky Derby, still holds the record for the fastest winning time.

Who is Secretariat?

400

This planet is the ruling body of both Taurus and Libra, and is associated with love and beauty.

What is Venus?

400

This 2008 single was rewritten due to the line "So go and tell your friends that I'm obsessive and crazy. That's fine, I'll tell mine you're gay." 

What is Picture to Burn?

400

This poorly described book plot involves a girl ruining her sister’s chances of appearing in a reality tv show

What is The Hunger Games?

400

This process introduces oxygen to wine, often by pouring it into a special container before serving.

What is decanting?

500

The Kentucky Derby is the first leg of this three-race series in American horse racing.

What is the Triple Crown of Thoroughbred Racing? (Triple Crown is acceptable) 

500

These two signs—Sagittarius and Pisces—are traditionally ruled by this largest planet in our solar system.

What is Jupiter?

500

Her grandmother, who inspired the Folklore song of the same name, was a professional opera singer.

Who is Marjorie Finlay?

500

The full name of Violet Sorrengail's unit in Fourth Wing, after they are switched from their initial placement to be in Xaden Riorson's wing.

Second Squad, Flame Section, Fourth Wing

500

This fast food chain, founded in 1965, has the most locations in the United States as of 2026. 

What is Subway?