Wedged between the best love songs and the best breakup songs lives the ideal Taylor Swift song: a combination of salty and sweet, openhearted but unafraid to give a disappointing lover a good kiss-off. It's a little dizzying to think about how many of those she's packed into just five albums. Here are the top 10 as ranked by our panel of expert Swiftologists.
Best Taylor Swift Songs
“Love Story” (2008)
It was only a matter of time before T-Swift took on the ultimate teenage love story: Romeo and Juliet. Her take on the star-crossed lovers doesn’t disappoint, though she does fudge the ending a bit (it’s just a story after all).
“Back to December” (2010)
Is it a breakup song or a take-me-back tune? Either way, the opening verse of this Speak Now song perfectly captures the mundane small talk between two people with a lot of baggage between them, then gets into the heavy stuff.
“I Knew You Were Trouble” (2012)
In less-skilled hands, the song’s pop-gone-EDM breakdown would reek of genre-hopping desperation, but Swift matches it with a powerhouse vocal turn and nails it.
“Tim McGraw” (2006)
Written when she was just a high-school freshman, this song is more than just a harbinger of things to come (though it’s certainly that too)—it’s still one of her best songs about young love.
Written as a takedown to detractors, this song proves that if you’re not going to just shake if off and let the haters hate-hate-hate, you might as well write a hit song about it.
Couched among the sugary chorus, this Red single has some deep insights. (”We're happy, free, confused and lonely in the best way,” she sings) We can’t wait to see what she has to say about 26 or 29 or 32.
On this Fearless track, Taylor warns her high-school pal of duplicitous older dudes, but as we later see (ahem, “Dear John”), they aren’t so easy to shake.
“You Belong with Me” (2010)
If you’ve ever had a crush on your BFF, this shout-along Speak Now tune’s inclusion is self-explanatory. Despite the Vogue covers and hundreds of millions of dollars, Swift plays the role of a T-shirt-and-jeans every-gal expertly.
As part of Taylor’s transition to pop, the moody pulse and sleek car-commercial-esque vibe make this this 1989 tune a perfect anthem for our celebrity-obsessed times.
“Our Song” (2006)
This song from her debut LP is Taylor is at her twangiest—fiddle solo and all—singing about high-school love like few can, actual high schoolers or otherwise.
Listen to the 10 best Taylor Swift Songs
Looking for more country tunes?
Don’t Tell Mama
What good is singing alone in your room when you can sing along with show tunes at a Theater District cabaret? Cabaret performers often congregate in the bar area before and after their numbers, and best of all, there’s no cover charge there, just a two-drink minimum. Sip a bourbon, hum a few bars, and soak up the Art Deco chic.