Today, October 24, 2026, marks the 20th anniversary of the release of Taylor Swift’s self-titled debut album. It will be at least a few years before anyone will truly consider this a monumental or transformative event — for country music, then for pop, then for pop culture as we knew it and continue to know it. Who knew, when she sang on “A Place in This World” while on “The Outside” at 16, that she would become the ultimate insider and biggest star in the music world? A visitor from the future making such claims in October 2006 would have been laughed in his time machine, as Swift’s team virtually begged for reporters’ interest in interviews and struggled to convince country radio to take a chance on a kid who checked exactly none of the right boxes.
It’s unclear if Swift is baking a cake or doing something else to celebrate her baby’s 20th birthday. She’s not marking it by doing something as obvious or fan-service-y as releasing a deluxe version of “Debut” (as it’s unofficially called, for convenience). She leaves the world of Swifties to throw their own party for a record that changed everything, first for the star herself, but also beginning the process of radically resetting expectations for how open, confessional pop superstars would forever be invited to be, especially as women took over after the boy band wave had gone overboard.
Speaking of time machines: let’s go back to when “Debut” was at its peak, although still far from the heights it would reach with its sequels. I interviewed Swift extensively for Entertainment Weekly on several occasions between the release of her debut album and “Fearless.” The first time was in early 2007, when she was having her hair and makeup done for the ACMs in Las Vegas. The second, more substantive interview took place in January 2008, at an In-N-Out hamburger restaurant just outside Universal City. As hard as it is to believe now, only one person approached her for an autograph for the entire hour plus we were sitting there enjoying our double-doubles. The vast majority of his success at the time was in the country sphere, which was much more isolated from pop then than it is today. And since Los Angeles isn’t the center of the country, that might explain why we were able to talk virtually without interruption. But MTV was just starting to experiment, giving a few spins to a “pop remix” of “Teardrops on My Guitar,” hoping that this Nashville cowgirl would be more exciting than daunting for the “TRL” audience. How brave they are, aren’t they?
Only a few hundred words of excerpts from that In-N-Out interview appeared in my coverage at the time. Today, on the 20th anniversary of “Taylor Swift,” I revisited those tapes and am happy to bring up for the first time a largely unabridged Q&A from that conversation, offering a good look at her early career and how she thought about the songs on “Debut” back then, now that she’d been a wise 18-year-old woman for about a month.
Looking back on my notes, I remember being struck by a culinary peculiarity that could have counted as diet advice: Swift didn’t drink all of her shake; she used it as a dip for her fries. Maybe I should revisit this Universal City In-N-Out this weekend, sit at the same table and see if they had anything with this dining formula. Hundreds of millions of US album and singles certifications later, we tend to trust his judgment.
Fast: (Talk to Paula Erickson, then a publicist, who picks up her order.) I want #2 without onions and a chocolate shake… (Turning towards me.) It doesn’t count if you eat it outside of town. It’s a rule.
Since you’re not from here, when was your first In-N-Out experience?
My first In-N-Out Burger experience was probably about a year ago. I was hooked, and it’s a deep love. This is profound.
Your publicist, Paula, and I had a disagreement. She said she loved coming here but hated the fries.
How could she say that? How could she say that? Oh my God. No, the fries are amazing. She just needs to open her mind to fresh fries. They make everything fresh. How can you not like it?
You were on the Leno show last night. How was it?
This was my second time playing Leno. It’s cool, he’ll bring you a gift every time in the locker room. The first time it was a watch; the second time was this really cool cover. Jay always comes to say hello, no matter who you are or where your single is on the chart.
I’ll let you in on a secret: I’ve been to the performers’ dressing room several times and Jay always stops by, but I haven’t seen him bring a gift to anyone else.
(Laughs.) They just know how to treat their guests.
You have two songs on the chart: “Our Song” is huge in country, and “Teardrops on My Guitar” is just starting to give you some of your first top 40 airplay. Was it difficult to decide what to do?
Whoever is #1. For me, it was a no-brainer to play “Our Song,” as it just spent its sixth week at No. 1 on the country charts. And in “Dick Clark’s Rockin’ New Year’s Eve,” I got to play both. But when I have a choice, I usually choose the one that’s higher on the charts. I’m going to milk this number 1 for all it’s worth.
It’s surprising that neither of the previous two songs went to #1 in country, in retrospect (“Teardrops on My Guitar” peaked at #2).
I was lucky that the songs had a very good impact with people. They never reached number 1 status on the charts, but I felt like they both did something really good for my career. But to have my first number 1 be a song I wrote myself in 9th grade for my high school talent show is pretty surprising. I didn’t even see that one coming. So it’s very exciting to be No. 1 and stay No. 1.
Taylor Swift at the 2007 CMT Music Awards – at the Curb Event Center at Belmont University in Nashville, Tennessee, United States.
FilmMagic, Inc.
There are probably people who are still wary because of your age, the fact that you actually write the songs… but looking at the ones you wrote yourself, no one can look at “Our Song” and doubt that you are a songwriter.
THANKS. I’m actually really glad that this was the song that was my first number 1, because it kind of says something. I’ve always wanted that respect from the Nashville songwriting community, and this year I was fortunate to receive the NSAI Songwriter of the Year Award, which is voted on solely by the songwriters. And getting my first number 1 with a song I wrote myself really means a lot to me.
Being older, a lot of times I don’t connect specifically to quote-unquote teenage music…
Don’t be offended, it’s OK!
But all that to say that while I don’t always have a lot of nostalgia for being that age, there’s something about the sweet specificity of “Our Song” that I can listen to and, for at least three minutes, go, okay, maybe I’d like to be a teenager again.
Oh, that’s really nice. THANKS. It was one of those songs that I wrote in 20 minutes, I literally sat down and wrote the whole thing. You know, I never expect to win if I’m nominated for an award. I never expect a song to go #1 if I release it. I would never expect a song that I wrote myself in 9th grade would make the album, then be a single, then a #1.
You also wrote “The Outside” on your own.
I was 12, yeah.
And there’s a song from your recent Christmas EP that you wrote yourself.
I wrote “Christmas Must Be Something More” when I was 13. I like to go back and look at what I wrote when I was younger and include that, because there’s a place for it, and there’s a place for vulnerability and innocence in songwriting. I wrote “The Outside” about not fitting in at school – about the scariest feeling I’ve ever had, going to school and walking down the hall and looking at all these faces and not knowing who you’re going to talk to that day. It’s scary when you’re 12 years old. I mean, it’s scary at any age to experience that. And a lot of people ask me: How did you get the courage to join record labels when you were 12 or 13 and go straight into the music industry? It’s because I knew I could never feel the kind of rejection I felt in middle school. I could never feel that way in the music industry, because they’re polite. If they tell you no, at least they will be polite about it. …First of all, I didn’t know any better. And second, I didn’t have the most perfect social life in college, so I guess that prepared me for the real world, in a sense.
You mentioned it in your first interview last spring, and at the time I was wondering why did she feel that way? Someone would look at you and think you’re one of the popular kids. But you were clearly precocious, did that separate you from your classmates?
I think what separated me was that on the weekends, all the friends I had were already starting to party – they were going to parties, starting stealing alcohol from their parents. And I was never interested in that. I was never even tempted by that. What I did on the weekends was go to songwriters’ nights, play guitar for people, sneak into karaoke bars, go to festivals and plug my guitar into little crackling amplifiers – that’s what I did. So I think it naturally separates you, if you don’t do the…
Gn entert
