90 Shades of Red—Every Taylor Swift Song Ranked, From Worst to First

Taylor Swift Song Ranking
Posted on 10/23/2012 at 11:59 AM

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The Popdust Files: music, Swifties, taylor swift, videos

taylor swift best songs

On June 19th, 2006, Taylor Swift released her debut single Tim McGraw for digital download and CD single purchase.

In the six-plus years since then, right up until her release of fourth studio album Red this week, Taylor has released 89 more songs for commercial consumption, the sum total of which–along with some iconic videos, a steady touring presence and enough off-court tabloid fodder for a couple literary anthologies—have resulted in her rising to one of our country’s best and biggest pop stars.

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In honor of Red‘s release, we’ve undertaken the task of ranking each and every one of those 90 songs in Taylor’s catalogue, from worst to best. That includes not just the tracks from her four studio LPs, but every bonus track, every compilation contribution, every guest appearance, every holiday-themed recording, and every iTunes-only cover. (In the case of a song that was released in multiple versions, we’ve listed the version we like best.)

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Read through our list, listen to the songs you’re not already familiar with—or with some of the songs towards the bottom, maybe don’t—and then let us know in the comments section about your own rankings, and how we messed up in our ranking of your favorite Taylor song.

Let us Speak Now, or forever hold our peace…



Found On: Sounds of the Season: The Taylor Swift Holiday Collection

One of the two original compositions on her holiday EP, “Christmas Must Be Something More” is Taylor’s somewhat awkward attempt at a Christmas song with a more religious bent, including lyrics like “So here’s to the birthday boy who saved our lives.” Unsurprisingly, Taylor upheld a separation of church and state in her music from that point on.


Found On: Non-Album Single

Taylor’s cover of Tom Petty & the Heartbreakers’ ’70s pop/rock classic should have been a slam dunk, but somehow her version saps all the energy and exuberance out of the original, leaving it a middling and forgettable country-pop rave-up. We feel she could do a lot better today with a mulligan on this one.

88. “BOTH OF US”

Found On: B.o.B.’s Strange Clouds

This one isn’t really Taylor’s fault, as the low ranking of “Both of Us” owes far more to the song’s unimpressive dubstep-goes-accoustic production and B.o.B.’s own forgettable presence on the verses then Taylor’s highly competent singing on the hook, but it’s just not a very good song. Too bad Swift’s buddy Hayley Williams beat her to singing on the far superior “Airplanes” a couple years earlier.



Found On: Sounds of the Season: The Taylor Swift Holiday Collection

Taylor was simply too young at the time of her holiday EP to take on a song as lusty as “Santa Baby,” and her version sounds less like her attempting to seduce St. Nick than it does her hoping to get a chance to play board games and dunk cookies with him. It’s still far less unsettling than Michael Bublé’s “Santa Buddy” from last year, though.



Found On: Taylor Swift

One of the first songs Taylor ever wrote, and it sounds like it, a disarmingly self-conscious song for a performer usually as self-assured as Swift. It’s not bad, but Taylor’s songwriting is a lot better on the outside of relationships than on the outside of social cliques, and Taylor would graduate to the In Crowd so quickly that “The Outside” makes for an odd listen these days.



Found On: Sounds of the Season: The Taylor Swift Holiday Collection

Taylor gives a somewhat overwrought version of one of the more lovely, low-key Christmas traditionals, making it sound like one of her heartbreak ballads. Can’t blame the girl for trying, but it’s not really our taste.


Found On: Speak Now World Tour Live

“You guys have a lot of amazing bands from this part of the world, did you know that?” No, Taylor’s not talking about the Beach Boys, The Doors, Fleetwood Mac, Red Hot Chili Peppers, or any of the other legendary bands to come from the West Coast—rather, she’s expressing her fondness for ’00s pop scourges Train, as she launches into their deplorable breakout hit “Drops of Jupiter.” Taylor’s performance is typically lovely, but not even she can save lyrics like “She checks out Mozart while she does Tae Bo” or “The best soy latte that you ever had…and me.” At least it’s not “Hey Soul Sister”…which Swift also covered in part on the Fearless tour. Why, Taylor, why????


Found On: Fearless: Platinum Edition

“Other Side” is mostly notable for being a sort of compendium of Taylor’s most relied-upon lyrical cliches, including slamming doors, little black dresses, suitors throwing pebbles at windows, and of course, meaningful encounters in the rain. Perhaps a good instructional tool for Swift, but certainly not one of her better songs.



Found On: Fearless: Platinum Edition

A forgettable bonus track that probably wouldn’t rank as any Taylor fan’s least or most favorite song of hers—though from here on in the list, every song ranks as a six out of ten at the least.



Found On: Taylor Swift: Special Edition

Another unextraordinary Taylor bonus track, though at least this one has an interesting guitar breakdown and a memorable (and quintessentially country) lyrical hook: “Why would you wanna break a perfectly good heart?” If there are any other lyrics in the song though, we can’t remember what they are.

For songs #80-71, click NEXT.

Other pages: #90-81, #70-61, #60-51, #50-41, #40-31, #30-21, #20-11, #10-1

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