Q 01/05

Swift's 2006 debut single was named after which country star?

A) Garth Brooks

B) Keith Urban

C) Tim McGraw

D) Kenny Chesney

Answer · why

C) Tim McGraw

Tim McGraw, the song's namesake, later took Swift on the road as an opening act on his Soul2Soul tour with Faith Hill.

Q 02/05

Which social network did Swift use to reach teenagers with her debut?

A) Friendster

B) Facebook

C) Bebo

D) Myspace

Answer · why

D) Myspace

Myspace let Swift share her own blogs and song news with fans, reaching teenagers whom country music marketing had long ignored.

Q 03/05

Which two debut-album singles topped Hot Country Songs?

A) The Outside and Our Song

B) The Outside and Picture to Burn

C) Picture to Burn and Should've Said No

D) Our Song and Should've Said No

Answer · why

D) Our Song and Should've Said No

Our Song and Should've Said No were both written by Swift alone; she wrote the first for her ninth-grade talent show.

Q 04/05

A showcase at which Nashville venue led to Swift's Big Machine record deal?

A) Grand Ole Opry House

B) The Bluebird Café

C) Ryman Auditorium

D) Tootsie's Orchid Lounge

Answer · why

B) The Bluebird Café

The Bluebird Café is where Scott Borchetta watched Swift play and promised her a deal as soon as he started his own label.

Q 05/05

Fearless made Swift the youngest Album of the Year winner until which singer broke the record?

A) Olivia Rodrigo

B) Billie Eilish

C) Ariana Grande

D) Lorde

Answer · why

B) Billie Eilish

Billie Eilish took the record at 18 in 2020, with a debut album made in her brother's bedroom studio at the family home.