Taylor Swift (2006)
Fearless (2008)
Speak Now (2010)
Red (2012)
1989 (2014)
100

what song contains the lyric, "I was ridin' shotgun with my hair undone in the front seat of his car" ?

"Our Song"

100

who plays the girlfriend in the "You Belong with Me" music video?

Taylor Swift

100

What song from this album did she famously perform at The Grammy's that year?

"Mean"

100

How long was the first draft of "All Too Well"?

10 minutes. 

100

Taylor's group of friends at the time was known as...

'The Squad'

200

What was the lead single from Taylor Swift (2006)?

"Tim Mcgraw"

200

What song on this album gave Taylor Swift her first #1 hit?

"Love Story"

200

What is track 5 of Speak Now?

Dear John

200

Who stars in "All Too Well: The Short Film"?

Sadie Sink and/or Dylan O'Brien

200

This alum was the first time Taylor worked with a producer named who?

Jack Antonoff

300

Who accompanied Taylor Swift to the MTV awards during this time, making it her first public boyfriend?

Joe Jonas

300

What song on the album is a cover of a previously death-metal song?

"Untouchable"

300

How many years apart where John Mayer and Taylor Swift?

13 years

300
What song contains the lyric, "Since you admitted it/ I keep picturing/ her lips on your neck/ I can't unsee it"?

"Babe"

300

What music video depicts Taylor in a truculent snow storm at one point.

"Out of the Woods"

400

What TWO songs on this record were edited and re-released a year later by Big Machine Records?

"Picture to Burn" and "Teardrops on my Guitar"

400

When she Re-recorded Fearless, how many songs "from the vault" did she release with it?

Six songs. ("You All Over Me", "Mr. Perfectly Fine", "We Were Happy", "That's When", "Don't You", "Bye Bye Baby")

400

How many song did Taylor write alone on this album?

All of them.

400

While on her Red tour, what company did she partner with to promote their product and the song, "22"?

Coca-Cola

400

"Wildest Dreams" was awkwardly produced by which ex-boyfriend?

Calvin Harris

500

This album gave Taylor her first grammy nomination. What category was she nominated for?

Best new artist

500

Along with 1989, what rare achievement of awards have both these albums collected?

1989 and Fearless are both the most awarded albums ever of their genre.

500

Taylor Swift interestingly composed a 27-second intro and outro for her song "Last Kiss", what personal event was this referencing? 

When Joe Jonas broke up with her in a 27-second phone call.

500

How long was the ORIGINAL recording of "All Too Well"?

about 40 minutes.

500

While doing an interview on the Ellen show, what did Taylor reveal her biggest fear to be? 

Sea Urchins