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100

The Nitty Gritty Dirt Band covered my song "Mr. Bojangles". Their version is more famous than my original version 

Who is Jerry Jeff Walker 

100

I am the mascot for an NBA team above the Northern US border.

Who is the Raptor (from the Tronto Raptors)?

100

I love me some movies.

Who is Dustin?

100

John consistently talked about this restaurant ever since we tried to go one time. We actually went on Tyler's last day.

What is Cracker Barrel?

100

My team and I had a 10 episode mini-series done on our last season.

Who is Micheal Jordan?

200

I collaborated with Ed Sheeran and Chris Stapleton on a song called "Blow"

Who is Bruno Mars?

200

I'm an anthropomorphic baseball. My team plays at Citi Field.

Who is Mr. Met.

200

I typically wear T-Shirts that are from places that my family has been. 

Who is Riley? 

200

This burger place on Thompson was one of our favorites. 

What is Hugh Babys?

200

I was taken late in the 6th round of the 2000 NFL draft. I Played my old team last night for the first time since leaving. I can be considered a GOAT

Who is Tom Brady?

300

This band from the '90s is almost synonymous with the grunge era.  The drummer from this band is now a frontman.

Who is Nirvana?

300

The team I cheer on is consistently always on top of college football ratings. 

Who is big Al?

300

I consistently blow people away with my computer skills.

Who is John?

300

This place is now located on Belmont blvd.

What is Athens?

300

While not a person, this wall is known by even casual Baseball fans.

What is the Green Monster.

400

I sang backup vocals on Dire Straight's song "Money For Nothing".

Who is Sting?

400

Surprisingly, this mascot of Florida State University has not been canceled.

Who is Chief Osceola?

400

I told our last intern about here thanks to her being an in-class aid for one of the Ideal classes while I was in the program. 

Who is Brad?

400

This place tore Riley's insides up.

What is Amaravati Indian? 

400

I'm known for wearing a black and white houndstooth hat.

Who is Bear Bryant?

500

This song by Phil Collins has one of the most recognizable drum parts. 

What is "In The Air Tonight"?

500

This mascot from Illinois rocks some red and black.

Who is Benny the Bull?

500

This person wrote a note to Matt when they accidentally ate Matt's cookies. 

Who is Dave Bers?

500

When put on the spot, Riley thought about taking us to this place in Green Hills

What is Corner Pub?

500

I won my last superbowl against the Carolina Pathers in Levi's stadium. That SuperBowl was also a big one.

Who is Peyton Manning?