Editor’s note: CMT.com and other MTV Networks websites throughout the world will provide a live stream of an album release event taking place Monday (Oct. 25) at 7 p.m. ET in New York City.
Taylor Swift hasn’t issued a greatest hits album yet, but she has certainly accumulated enough chart success to compile one. With her new album, Speak Now, arriving Monday (Oct. 25), the CMT.com staff reflected on 10 prime hits have kept her busy over the past five years.
“Fifteen” — I lost my virginity when I was 15. I gave everything I had to a boy, Eric, who changed his mind. So even though this song paints a much bigger picture of growing up, that line about Abigail buried in the last verse really gets to me. Not many artists can set that coming-of-age emotion to music. It’s a time in your life when you are as vulnerable as you are narcissistic, when you know everything but know nothing. This song makes it OK to have been in that place and come out on the other side. The older, wiser side. — Alison Bonaguro
“Love Story” — William Shakespeare really hit the jackpot with Romeo and Juliet. He wasn’t the first to write about young love, but his characters and plot development have inspired composers and songwriters ranging from Tchaikovsky and Prokofiev to Mark Knopfler and Lou Reed. The play also inspired Taylor Swift, although she decided — perhaps wisely — that nobody would die in her song. Of course, it’s hard to sing about death when the melody is as bouncy as the one she wrote for “Love Story.” It’s her upbeat, optimistic take on a theme that’s been around for centuries. — Calvin Gilbert
“Mine” — One of my friends firmly believes that until you’ve had a really big fight, you just can’t be certain that a promising relationship will last. In “Mine,” Swift faces a similar situation — an unlucky-in-love young woman with an ambitious crush. Almost immediately, she fantasizes about settling down with her cute waiter … then marries him and almost lives happily ever after, until they explode in anger at 2:30 a.m. All this before she’s even ordered a cup of coffee. Luckily, in her dream world, he swoops in for a serious case of reassurance and the song ends happily. OMG, my friend is right! — Craig Shelburne
“Our Song” — Every couple needs a song, don’t they? Swift puts a spin on this common practice with a cheerful tune. While most couples choose a well-known song to define their relationship, Swift goes the extra mile and creates her own — listing multiple memories she’s made with her significant other. The part that gets stuck in my head without fail is, “And when I got home, ’fore I said amen/Asking God if He could play it again.” Looks like her prayer was answered as fans played it again and again, making it her first No. 1 single. — Stephanie Pendergrass
“Picture to Burn” — After hearing this song for the first time, I felt as though Swift stole a few pages from my high school diary. The memory is burned into my brain. I was sitting at the kitchen sink, lighter in one hand and the picture of my first love in the other. As I began to light the image of our smiling faces, I was hoping to melt away the hurt, the sadness and the anger. I burned every picture I could find of the two of us. Though I felt instant relief, I also regretted my decision. All of our captured memories were ashes. What if I wanted to look back someday? Years later, I found a photo of the two of us that my mother had tucked away after she realized I was using her sink as a fire pit. In retrospect, there’s usually a lesson to learn from these small snapshots of life. Sometimes the heartache makes you stronger. — Whitney Self
“Should’ve Said No” — It must be really hard for songwriters to come up with new spins on done-me-wrong songs. So getting Swift’s take on the topic, with her youthful perspective and her wailing vocal, felt very fresh the first time I heard it back in 2008. It was so unique, I thought, to tell a cheater what should have happened (he should have resisted that moment of weakness) instead of just dwelling on how hurt she is. When she strings together that line about “you should’ve known that word ’bout what you did with her’d get back to me,” there’s a cadence to the way the words are spilling from her mouth, just like they would be if she was really trying to enlighten the bastard. — Alison Bonaguro
“Teardrops on My Guitar” — Anybody who’s ever been too shy to tell someone how they really feel can relate to this song. It doesn’t matter if you’re young or old, if you’re frozen by the fear of losing the connection that’s already there, you simply sit back and wind up in the “friend zone.” It’s painful and poetic — fertile ground for a country song — and Swift hit the nail on the head with the slick imagery of teardrops falling on a guitar. It was only her second single, yet it established her as an expressive songwriter with a knack for turning her personal experiences into universal truths. — Chris Parton
“Tim McGraw” — In 2006, when I first heard about the existence of a song called “Tim McGraw” by a new 16-year-old girl, I was very skeptical, to say the least. Trying to muscle in by name-dropping a star, I thought. Then I listened to the song. She won me over. It’s a very well-written, deeply evocative tale of a first love that ends too soon. The idea came while Swift sat in math class, thinking about a boyfriend who went off to college. After school, she met her writing partner, Liz Rose, and they reportedly finished the song in 15 minutes. It became her first single and peaked at No. 6 on the Billboard country single chart. She later revealed the unnamed song that is the thread in “Tim McGraw” was “Can’t Tell Me Nothin’.” Which, of course, is her favorite of his. Just think of it: Swift has oldies but goodies of her own from years ago. — Chet Flippo
“White Horse” — Swift is known for fairy-tale-inspired tunes, but this song offers a refreshing twist. As neither a sentimental love song nor a boy-bashing anthem, it reveals more of a quiet resolve. The dark, acoustic sound mixes perfectly with the heart-rending lyric. I can almost feel her gaining strength throughout the choruses until she finally reaches her breaking point and sets the boy straight by singing, “It’s too late for you and your white horse … to come around.” From the initial confusion and through the hurt to adopt an “over-it” attitude, she captures the complete scope of emotions that come with a breakup. — Andrea Graff
“You Belong With Me” — Swift is nothing if not whimsical, and in this infectious smash, she gleefully blots out all shades of gray. The popular cheerleader who has the guy is pure evil! The overlooked girl-next-door is a complete sweetheart! Cinderella! Jane Eyre! The Princess Diaries! It’s hardly the most rational outlook on love, so why can’t you stop singing along? Because the heart isn’t always rational, either. And Swift’s music is all about heart. — Dan Milliken