December to Remember
Ball or Nothing
Wicked Local
OK Boomer
Christmas Karaoke
100

FDR delivered his famous 'Infamy Speech' to Congress asking for a declaration of war following the December 7, 1941 surprise attack on this naval base

What is Pearl Harbor?

100

This future Hall of Fame pitcher holds the MLB all-time record for postseason strikeouts with 230

Who is Justin Verlander?

100

This quintessential Boston film, written by local legends Matt Damon and Ben Affleck, had its limited theatrical release in December 1997

What is Good Will Hunting?

100

If you hear some juicy gossip, you have to ask your friend to "spill" this hot beverage

What is tea?

100
The Ronettes: "Lets take the road before us and sing a chorus for two..."

What is "come on, it's lovely weather for a sleigh ride together with you"?

200

On December 8, 1980, music fans worldwide were devastated when this former Beatle was shot outside the Dakota apartment building in NYC

Who is John Lennon?

200

This most recent Triple Crown winning horse is the only one in history who was never beaten in his entire career

Who is Justify?

200

When ordering at a Dunkin' in December (or any month), asking for your coffee 'Regular' means it comes with these two things.

What is Cream and Sugar?

200

This Oxford 'Word of the Year' finalist refers to your ability to flirt and attract a romantic partner

What is rizz?

200

Wham: "My god I thought you were someone to rely on ..."

What is "Me? I guess I was a shoulder to cry on"?

300

This specific Amendment was ratified on December 6, 1865 formally formally abolished slavery and involuntary servitude, except as a punishment for crime.

What is the 13th Amendment?

300

In August 2016, this 12-time Olympic medalist caused an international incident when he fabricated a story about being robbed at gunpoint at a gas station in Rio de Janeiro

Who is Ryan Lochte?

300

In 1963, Worcester graphic designer Harvey Ball spent 10 minutes creating this iconic yellow symbol to boost morale at an insurance company; he was paid just $45 for the design

What is The Smiley Face?

300

If you walk into a room with an incredible outfit and effortless style, you are said to have this liquid-sounding quality

What is Drip?

300

12 Days of Christmas: "On the ninth day of Christmas, my true love gave to me..."

What is "Nine Ladies Dancing?"

400

On Christmas Day 1991, the Hammer and Sickle flag was lowered over the Kremlin for the last time after this Soviet President resigned

Who is Mikhail Gorbachev?

400

This former Patriots backup quarterback and Wester Kentucky star holds the NCAA D1 records for passing yards and touchdowns

Who is Bailey Zappe?

400

Every December, this Canadian province sends a giant Christmas tree to Boston Common as a thank you for the aid Boston sent following their tragic 1917 maritime disaster

What is Nova Scotia?

400

This meaningless hand motion popularized by TikTok users was Dictionary.com's 2025 Word of the Year

What is 6 7?

400

The Pogues: "The boys of the NYPD choir were singing 'Galway Bay' ..."

What is "and the bells were ringing out for Christmas Day"?

500

On December 14, 1911, this Norwegian explorer won the race to the bottom of the world, becoming the first person to reach the geographic South Pole

Who is Roald Amundsen?

500

In October 2017, the U.S. Men's National Team failed to qualify for the World Cup for the first time since 1986 after a shocking 2–1 loss to this dual-island Caribbean nation

What is Trinidad and Tobago?

500

In the late 19th century, this Massachusetts city was famously known as the "Shoe Capital of the World," leading global production of shoes, particularly women's footwear

What is Lynn?

500

If you notice a subtle insult, catch someone in a lie, or call someone out on their bad behavior, you are said to do this—which is also what you do to check the time

What is Clock It?

500

Thurl Ravenscroft: "You're a mean one, Mr. Grinch. You really are a heel. You're as cuddly as a cactus..."

What is "you're as charming as an eel"?

M
e
n
u