Though she only released her first album, the self-titled Taylor Swift, in 2006, Taylor Swift has had a meteoric rise to fame, especially considering she’s only 25. With more than 40 million albums sold, Swift went from sweet-hearted country-singin’ teen to mega-watt stadium star over just five albums, with her latest, 1989, marking the singer’s straight-up transition from country ditties to pop blockbusters.
Even though she’s released well over 30 singles that range from “pretty good” to “downright excellent,” some music fans might still have a hard time putting together a compendium of Swift’s greatest material. Yes, she’s a musical juggernaut, and yes, “Shake It Off” is a great song, but what has she really done, other than writing dozens if upon dozens of solid singles? And what can Swiftian Johnny Come Latelies garner from the singer’s earlier career?
Plenty, as it turns out. While Swift’s early material, including the aforementioned Taylor Swift, leans more country than pop, the singer still never waxed rhapsodic about whiskey or women, and while some—nay, a lot of her songs might be about lost love, that’s always been par for the course in both country and pop songwriting. Writing a good portion of her material from day one, Swift has always been in control of both her image and her sound, and so, while parts of her early material definitely sound like they were created by the teenager that Swift was at the time, there’s still a through-line of Swift’s general personality and sensibilities in all of her material. That’s something Swift fans have grown to know and love; Taylor Swift has and always will be Taylor Swift, for better or for worse.
While the challenges of creating a solid hour of Taylor Swift goodness are many—she’s released a lot of solid singles, for one—The A.V. Club managed to do it all the same, even coming in about two minutes under our allotted 60-minute maximum. Throw on a pair of Swift-endorsed high-waisted shorty shorts, grab your supermodel best friends and cats named after beloved television characters, and get listening.
1. “Shake It Off” (2014)
The only logical place to start a Taylor Swift mix made in 2015, “Shake It Off” is Swift’s emergence from her country cocoon. Helped along by co-writers and pop impresarios Max Martin and Shellback, Swift fully embraces her grown-ass ridiculousness here, reminding her generations of listeners that “haters gonna hate, hate, hate, hate, hate.”
2. “We Are Never Ever Getting Back Together” (2012)
Another of Swift’s poppier ditties, “We Are Never Ever Getting Back Together” has the kind of anthemic chorus that really helped Swift move from the cute country ghetto into the pop mainstream. Produced again by Martin and Shellback, “We Are Never Ever Getting Back Together” was the first song in Swift’s career to hit No. 1 on the Billboard Hot 100. Considering it’s sold about 7 million copies worldwide, it’s not really a sleeper hit, but that doesn’t make it any less of a banger.
3. “Our Song” (2006)
The third single off Swift’s eponymous debut, “Our Song” was actually written by a teenage Swift for her freshman year talent show. Seeing how popular it was with her high school classmates, Swift started playing the song out a bit more, and the rest was history. A perfect little country ditty about a young and simple couple, “Our Song” is a great example of both how talented Swift is as a songwriter (she wrote the track in about 20 minutes, she estimates) and of how she’s changed over her career. Decidedly less bombastic than anything on 1989, “Our Song” is the kind of sweet track that helped Swift break out but that, were she still singing this kind of stuff now, would have long ago consigned her to a very specific career track.
4. “Love Story” (2008)
A silly little take on Romeo And Juliet, “Love Story” finds Swift doing some of her most savvy blending of pop and country. A lilting track with plucky banjo and cutesy couplets, “Love Story” has Swift conjuring images of people and places with her words, and the chorus—well, it’s got sticking power. All that amounts to a certain je ne sais quoi that must have worked for Swift, considering “Love Story” has become one of the best-selling singles of all time, moving over 8 million copies to date.
5. “Should’ve Said No” (2006)
The fifth single off Taylor Swift, “Should’ve Said No” is one of those classic country songs about cheating lovers, something that’s made all the more impressive considering Swift wrote it when she was 16. With lines directed at the cheater admonishing him for not thinking “twice before you let it all go” and reminding him that, especially these days, “You should have known that word / Of what you did with her / Would get back to me,” it’s a solid anthem for all those ladies (and gents) who have had their hearts broken by a lazy, lying ex-lover.
6. “Mean” (2010)
The first song on this mix from Swift’s third album, 2010’s Speak Now, “Mean” found the singer shifting backward a little bit toward more traditional country music, abandoning some of the more poppy stuff she’d done before. With bluegrass banjo and plenty of stomping and hand-clapping, the track speaks a bit to what was going on in music at the time, especially with acts like The Civil Wars, Mumford & Sons, and so on.
7. “Blank Space” (2014)
Another poppy romp off 1989, “Blank Space” finds Swift once again alongside Martin and Shellback. This time, though, the trio is delving into the world of electro-pop, complete with electric drum hits and staccato lyricism. It’s a dramatic departure for Swift, especially set against something like “Mean,” but damn if it’s not an insanely catchy one as well. That chorus—“’Cause we’re young and we’re reckless / We’ll take this way too far / It’ll leave you breathless / Or with a nasty scar / Got a long list of ex-lovers / They’ll tell you I’m insane / But I got a blank space baby / And I’ll write your name”—is the kind of thing that’ll end up sparking drunken karaoke parties for years to come.
8. “I Knew You Were Trouble” (2012)
Yet another Swift, Martin, and Shellback joint, “I Knew You Were Trouble” really lives and dies in its chorus, which is another of those “bunch of drunk girls at a bachelorette party” jams. With a small amount of beat-dropping and swishy EDM influence, it’s probably not the kind of track that will age well in the long run, but for now, it’s a solid representation of Swift’s career trajectory.
9. “Forever & Always” (2008)
The first track in this Power Hour that isn’t a single, “Forever & Always” is a solid cut off Fearless, one of Swift’s better records. Similar in tone to “Love Story,” “Forever & Always” is another of Swift’s endearing break-up songs, but a relatively juicy one considering it was written about her heart-wrenching breakup with fellow pop star Joe Jonas.
10. “You Belong With Me” (2008)
Another Fearless cut about an off-balance romance, “You Belong With Me” is notable not just because of its catchy lyrics—which, like most of Swift’s material, ring out clear as a bell in the mix—but because of its video. The clip, directed by Roman White, finds Swift poking fun at her girl-next-door awkwardness by playing both the clip’s popular girl and its biggest dork. That kind of self-deprecation has come to grate on a lot of Swift’s detractors (including Kanye West, who interrupted the VMA speech Swift gave after winning an award for this video), but it’s something the singer continues to trade on both in her videos and on social media.
11. “Wildest Dreams” (2014)
Another song that hasn’t been released as a single—yet—“Wildest Dreams” sounds like Swift’s homage to the Drive soundtrack. (Note: That means it’s only available via iTunes and Apple Music and not on YouTube, much to the dismay of editors and teenagers everywhere.) Sweeping, dark, and revealing, the song blends notes of Katy Perry’s “Dark Horse” with a recorded and manipulated version of Swift’s own heartbeat, which forms the song’s backbeat.
12. “Teardrops On My Guitar” (2006)
Swift’s second single ever, “Teardrops On My Guitar” is a big musical departure from “Wildest Dreams,” but fits tonally. Once again, Swift is talking about love, heartbreak, and what she thinks she’s lacking, and while that might sound trite to some listeners and non-Swift fans, it’s the kind of material that makes Swift relatable to all sorts of listeners, young and old. If she doesn’t feel like she’s enough either, then you can’t be alone. “Teardrops On My Guitar” is the kind of song that reminds listeners that Swift gets it.
13. “Never Grow Up” (2010)
The Power Hour starts to slow down toward its end, most noticeably with “Never Grow Up,” an acoustic ballad Swift wrote on her first night in her first grown-up apartment. Addressed to a child—metaphorical, real, whatever—the song is full of heartfelt sentiment and reminders that, no matter how old we get, it’s always possible to remain young at heart.
14. “Fifteen” (2008)
Written once again when Swift was in high school, “Fifteen” introduced listeners to not only whoever the singer went on her first date with but to Swift’s longtime and real life best friend, Abigail. In this song, Abigail gets a bit of a bad shake after giving “everything she had to a boy who changed his mind,” but the whole track is a brilliant and poignant look at what it’s not only like now for high schoolers, but what it’s always been like. It’s crushes and new friends and drivers’ licenses, and all the happiness and sadness that comes along with all of that. It’s a hard sentiment to capture, and that Swift did it when she was just a teenager herself is remarkable.
15. “Tim McGraw” (2006)
Swift’s first single ever, “Tim McGraw” was the track that broke her at country radio, something that’s understandable given both the track’s storyline—yet another heart-wrenching breakup—and its superstar-friendly title. It’s not Swift’s best track, but it’s her first big break and every list deserves a sentimental favorite.
Total time: 58 minutes