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The Holidays
100

Nicknamed the sheriff, this NFL great rode off into the sunset with a win in Superbowl 50.

Who is Peyton Manning

100

In the song "Frosty the Snowman" This item made Frosty come to life.

What is an old silk hat

100

The invoice for one's prescription tablets.

What is a pill bill

100

This was the year Regina became the capital of Saskatchewan.

What is 1905

100

This reindeer who pulls Santa's sleigh also shares a name with a symbol of Valentines day.

Who is Cupid

200

Despite winning 3 Superbowl's in the 90's, this NFL team has not made a confrere final since 1996.

Who are the Dallas Cowboys

200

Written in 1953, this Johnny Cash chart topper was later played in location the song is about.

What is Folsom Prison Blues

200

One who chooses the alcohol.

What is a liquor picker

200

After appearing in "Smokey and the Bandit" and "Knight Rider" this car became a pop culture icon.

What is the Pontiac Trans AM

200

"O Christmas Tree" was originally sung in this language 

What is German

300

This "Original 6" hockey team has the fewest Stanley cups of the Original 6.

Who are the New York Rangers

300

This was Jimi Hendrix's only top 40 hit.

What is All Along the Watchtower

300

A quick peace contract.  

What is a speedy treaty

300

Sometimes used by economists, the "Big Mac Index" measures this.

What is purchasing power

300

Celebrated commonly in Canada, the U.K., Australia and New Zealand, this post Christmas holiday is not celebrated in the U.S.

What is Boxing Day

400

His walk off home run in 1993 won his team a World Series, their second of a back to back.

Who is Joe Carter

400

Billie Eilish became the youngest person to win 2 Oscars, winning for songs in these two movies.

What are James Bond "No Time to Die" and Barbie

400

Stocking fillers for terrible golfers.

What are stuffers for duffers

400

This is what the Statue of Liberty wears on her feet.

What are sandals.

400

This traditional Christmas decoration is actually a parasitic plant.

What is Mistletoe

500

With 4 picks in the game, this Roughrider was named the 2007 Grey Cup MVP

Who is James Johnson

500

This Marvel actress was briefly a part of the band Metric for a special rendition of the song "Black Sheep" for the movie Scott Pilgrim vs. The World

Who is Bre Larson

500

The kidnapping of builders and tools from their work site.

What is a construction abduction

500

This is the oldest currency still in use today.

What is the British Pound.

500

According to buddy the elf these are the 4 main food groups.

What are Candy, Candy Canes, Candy Corns and syrup