BOSTON — Two days to go. We have told the story of how the debut was made, walked through every song and followed the radio tour. Now it is your turn. Eleven songs, head-to-head, until only one is left.

How to play

Every matchup is between two songs from the standard edition of Taylor Swift. Pick the one you would rather hear right now. Winners move on, and if a round has an odd number of songs, one gets a bye. The order is shuffled every time, so play twice and see if your champion holds up.

Taylor’s Version watch

The other question fans are asking this week is whether a re-recorded debut is on the way. Here is what is on the record:

• 2019: Big Machine Records was sold, and the master recordings of her first six albums, including the debut, went with it.
• 2020 onward: Taylor began re-recording those albums as “Taylor’s Versions,” releasing four of them.
• May 30, 2025: She announced she had bought back the masters of all six albums. In the same letter she said the debut re-recording was finished, and that it could still re-emerge when the time is right.

As of our deadline, no release date for Taylor Swift (Taylor’s Version) had been announced. We will be watching on October 24, and so will everyone else.

Sources

• Wikipedia: Taylor Swift (album))
• WAMC / NPR: Taylor Swift buys back the rights to her first six albums (May 30, 2025)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — In 2006, there was no playbook for a teenage country artist on a brand-new independent label. So Taylor Swift and Big Machine wrote one. The debut album found its audience the old-fashioned way and the brand-new way at the same time.

Station by station

“Tim McGraw” went to country radio in June 2006, four months before the album came out. Then Taylor went on the road, visiting radio stations across the country on a radio tour that lasted about six months, through the end of the year. It was slow, unglamorous work: introducing herself, playing the song live and thanking programmers one station at a time. It worked. The single reached No. 6 on Hot Country Songs.

The Myspace generation

At the same time, Taylor was doing something few country artists did: talking to fans online. She used Myspace to post blogs and share song information, and it drew in teenagers and young adults who did not necessarily listen to country radio. That direct line to fans became a hallmark of her career.

Opening for the biggest names in country

The live shows came next. Taylor opened for Rascal Flatts in late 2006, then for George Strait in early 2007, toured with Brad Paisley through 2007, and in July 2007 opened for Tim McGraw and Faith Hill, the couple whose name was on her first single.

Crossing over

By 2007, “Teardrops on My Guitar” had crossed from country into pop radio, reaching No. 13 on the Hot 100 and the Top 10 on several pop and adult formats. More than a year after release, the album kept climbing, peaking at No. 5 on the Billboard 200 in January 2008.

The lesson

Show up, play the song, talk to your fans yourself. Twenty years later, it is still a pretty good marketing plan.

Sources

• Wikipedia: Taylor Swift (album), release and promotion)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — Forty minutes and 28 seconds. That is the entire running time of the standard edition of Taylor Swift, 11 songs that introduced one of the defining songwriters of her generation. Every song carries her name in the credits. Here is the whole album, one track at a time.

1. “Tim McGraw”

Written by Taylor Swift, Liz Rose · 3:54

Nostalgia for a relationship with an older boyfriend, built around the songs that remind you of someone. It became the first single.

2. “Picture to Burn”

Written by Taylor Swift, Liz Rose · 2:55

A sharp, funny kiss-off to an ex who did her wrong. It reached the country Top 10.

3. “Teardrops on My Guitar”

Written by Taylor Swift, Liz Rose · 3:35

Unrequited love for a boy who likes someone else. Her first big crossover hit, reaching No. 13 on the Hot 100.

4. “A Place in This World”

Written by Taylor Swift, Robert Ellis Orrall, Angelo Petraglia · 3:22

A teenager’s uncertainty about where she belongs and what comes next.

5. “Cold as You”

Written by Taylor Swift, Liz Rose · 4:01

A relationship with someone who never appreciated her.

6. “The Outside”

Written by Taylor Swift · 3:29

Loneliness after her love of country music set her apart at school. One of three songs she wrote alone.

7. “Tied Together with a Smile”

Written by Taylor Swift, Liz Rose · 4:11

Written about a friend struggling with an eating disorder, and about how people hide pain behind a smile.

8. “Stay Beautiful”

Written by Taylor Swift, Liz Rose · 3:58

Admiring someone from afar, without him ever knowing.

9. “Should’ve Said No”

Written by Taylor Swift · 4:04

Confronting a cheating ex. Written alone, it became her second country No. 1.

10. “Mary’s Song (Oh My My My)”

Written by Taylor Swift, Liz Rose, Brian Maher · 3:35

A love story that lasts from childhood to marriage.

11. “Our Song”

Written by Taylor Swift · 3:24

A couple who make a song out of their everyday moments. Written alone, it went to No. 1 on Hot Country Songs.

The writers’ room

Seven of the 11 songs were co-written with Liz Rose, who met Taylor through her publishing deal and became her most important early collaborator. Robert Ellis Orrall and Angelo Petraglia co-wrote “A Place in This World,” and Brian Maher joined Taylor and Rose on “Mary’s Song.” Three songs, “The Outside,” “Should’ve Said No” and “Our Song,” are Taylor’s alone.

A note on “Tied Together with a Smile”

One of the album’s quietest songs carries one of its heaviest subjects. If you or someone you love is struggling with an eating disorder, support is available from the National Alliance for Eating Disorders.

Sources

• Wikipedia: Taylor Swift (album), track listing and songs)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.