General geography
Flags
Country statistics
Matt trivia
21st century teenage slang (courtesy of Dre)
100

The northernmost state in the USA

What is Alaska?

100

The countries flag with a maple leaf on it

What is Canada?

100

The country with the lowest crime rate

What is Iceland?

100

Matt played this sport in middle school but did not make the A team in high school so he quit

What is Basketball? 

100

This word means to have charisma

What is "Rizz"?

200

The country(ies) Mount Everest is in

What is China? or What is Nepal? Either are acceptable

200

The countries flag is in the top left of various other countries flags, such as Australia and Tuvalu

What is The United Kingdom

200

The country with the most dogs

What is the USA?

200

Despite gazillions of trips to the orthodontist, Matt has never had these on his teeth

What are braces?

200

This word means to be "the greatest of all time" at something

What is the GOAT?

300
The country that I am thinking of

Azerbaijan

300

These countries flags dimensions differ from that of the traditional countries flag

What is Monaco? Or what is Switzerland?
300

The country with the highest population density

Monaco

300

Matt's favorite rapper

NF

300
This word means to ignore someone, typically without explanation 

What is ghosted?

400

The country with the most islands in the world

What is Sweden?

400

One of the two country flags that have purple on it 

What is the Spanish flag? or what is the Mexican flag?

400

The country with the lowest population density

What is Mongolia?

400

Matt used this to get around town as a youngster, because as he so elegantly put it, "Scooters are for posers"

What is a skateboard

400

This term means to allow someone to freely let a person do something they are good at, or in gen z terms to "pop off" or "slay". (These are not the answer I just thought I'd include them)

What is "let him cook"?
500

The country with the highest average elevation

What is Bhutan?

500

The only countries flag without red, white, or blue on it

What is Jamaica?

500

The country with the highest HDI

What is Switzerland

500

Matt has been to both the north and south ____

What are poles?

500

This word is used amongst the youth to say that a food tastes good, or is:

What is "bussin"?