Boston Made Stories
Road to the Rocketship, Ch. 6: Kingswell Opens a Restructuring Desk
Kingswell Strategic Ventures is building a corporate restructuring processor — a guided tool for entity restructuring, operational turnarounds, creditor workouts and M&A preparation. A free demo comes first; full use unlocks with MasterPass.
Boston Made Stories
The Debut Bracket: Pick the Greatest Song on Taylor Swift’s First Album
Eleven songs from the 2006 debut, head-to-head, until one is left standing. Plus where things stand on a debut Taylor’s Version. Part five of our Countdown to 20.
Dear Sir or Madam,
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.
The Debut Bracket
Eleven songs. One champion.
Tap your favorite in each matchup. Songs are seeded in random order every time you play.
Your debut champion
Twenty years later, still undefeated.
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 Made Stories
Radio Stations, Myspace and Opening Slots: How Taylor Swift’s Debut Found Its Audience
A six-month radio tour, a Myspace page and opening slots for Rascal Flatts, George Strait, Brad Paisley and Tim McGraw and Faith Hill. How the debut was built, one fan at a time. Part four of our Countdown to 20.
Dear Sir or Madam,
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.
Trivia · 5 questions
On the road with the debut
Test your knowledge of how the album found its fans.
01 / 05
When did “Tim McGraw” go to country radio?
June 2006, four months before the album.
02 / 05
How long was the radio tour that followed?
About six months, through the end of 2006.
03 / 05
Which social network did Taylor use to share blogs and songs?
Myspace, where she connected directly with teenage and young-adult fans.
04 / 05
Whose tour did she open in late 2006?
Rascal Flatts, after another act was dropped from the bill.
05 / 05
Which couple did she open for in July 2007?
Tim McGraw and Faith Hill, the subjects of her first single’s title.
Sources
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 Made Stories
Track by Track: Inside the 11 Songs of Taylor Swift’s Debut Album
All 11 songs on the original 2006 album: who wrote them, how long they run and what each one is about, plus a name-that-track game. Part three of our Countdown to 20.
Dear Sir or Madam,
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.
Match game · 6 questions
Name that track
We describe the theme. You pick the song.
01 / 06
The theme: feeling left out because of your love of country music.
“The Outside,” track 6, written by Taylor alone.
02 / 06
The theme: a love that lasts from childhood all the way to marriage.
“Mary’s Song (Oh My My My),” track 10.
03 / 06
Which track is the shortest on the album?
“Picture to Burn” runs just 2:55.
04 / 06
Which song closes the album?
“Our Song,” track 11.
05 / 06
How many songs did Taylor write entirely on her own?
Three: “The Outside,” “Should’ve Said No” and “Our Song.”
06 / 06
Which track has three credited writers?
“A Place in This World” (with Robert Ellis Orrall and Angelo Petraglia). “Mary’s Song” also has three.
Sources
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.
The Debut Bracket: Pick the Greatest Song on Taylor Swift’s First Album
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