20. Great Good Fine OK — Midnight Rain
For their 2023 cover of “Midnight Rain,” the synthpop duo Great Good Fine Ok reworked the track into a smooth R&B slow-jam. Shifting tempos and grooves throughout, the duo created a tune that channels different eras of R&B and might have felt at home on the radio circa 1982. The track ends with a stunning sax solo that harkens back to the golden age of Yacht Rock. Perhaps Swift could explore these eras, too. — Curtis Zimmermann
19. Postmodern Jukebox ft. Tia Simone — I Knew You Were Trouble
If you’re a Postmodern Jukebox fan, you know by now what you’re getting from one of their covers: a radical rearrangement, often involving piano and horns; a guest vocalist whose talent far exceeds their fame; a live one-take video where everyone faces front and steamrolls you with their proficiency. And you’re cool with that. With a performance like “I Knew You Were Trouble,” well you might be. Tia Simone wails, the new arrangement (they call it Motown, I think it’s more jazzy) fits the song like a gelatin glove, and you’re going to be sooooo jealous of the energy coming off tambourine guy in waves. — Patrick Robbins
18. Aaron Watson ft. Jolee Kate Watson — Never Grow Up
Country singer/songwriter Aaron Watson probably didn’t see himself covering Taylor Swift at any step along the way up–it’s still not the best look for a Texan cowboy. But now that he’s successful and (at the time of recording) father of a 14-year-old daughter, why not? When daughter Jolee Kate Watson joins in on the “Don’t you ever grow up” refrain, any parent in earshot will tear up. This is a syrupy rendition, sure, but straight from the heart all the same. It’s from Watson’s Cover Girl album, on which he recorded songs by contemporary female songwriters. It was Jolee who insisted Swift be one of the songwriters included. (Jolee Watson may be a Swiftie, but her voice brings to mind a young Alison Krauss.) — Tom McDonald
17. Shoshana Bean and Cynthia Erivo — I Did Something Bad
It’s really saying something that, even with two powerhouse Broadway stars singing, the strings steal the show in this sultry cover. The initial tango violin fades into the soft plucks that tiptoe in the verses. Sonorous cellos and bass lurk until the big confessional choruses where the strings lose their restraint along with the vocalists, bringing fitting drama to this Reputation-era song. — Sara Stoudt
16. Madaila — Cowboy Like Me
We’ve seen Vermont synth-pop artist Madaila around these parts covering up-tempo bangers by Whitney Houston and David Bowie. Those were full-band concert favorites, but, when lockdown hit early in the pandemic, frontman Mark Daly went for a softer choice for a one-man quarantine cover. His synthy new wave stylings still come through loud and clear though, even in a quieter setting. — Ray Padgett
15. Sabrina Carpenter — I Knew You Were Trouble
You might be thinking that the most well-known “cover” of this song involves a four-legged scream, but this version will make you smile just as much. Even before her breakout Short n’ Sweet album, Sabrina Carpenter had the confidence to change up the melody in this cover. We hear that country twang before Carpenter’s full pop crossover, much like Taylor Swift’s own path. The verses are airy and light, giving a touch of youthful naivety that contrasts with the more hardened, woman-scorned choruses. Even with the changes, this version still gives that cozy autumn Red-era feeling. — Sara Stoudt
14. Dan + Shay — Back To December
Swift’s (amicable) breakup with Taylor Lautner almost (but not quite) denied us some top class memes, but it did gift us a great song which showed us a different side to Swift. It is one thing to be a songwriter who can dissect the faults and irrational behavior of an ex, but an even greater songwriter can shine the torch on themselves, and accept that you were not always the perfect partner. The greats of country music have always been able to do this, and Swift is one of those greats. On their cover, Dan and Shay leave many things in place but they add a level of self-doubt that Swift, even when criticizing herself, finds more difficult to summon. — Mike Tobyn
13. The Dollyrots — You Belong With Me
Though “Love Story” sold more, “You Belong With Me” was the closest Swift had gotten to #1 in her young career, getting to #2 in 2009. And it makes sense because the country elements – the banjo, the mandolin, the fiddle – are all rather muted against the conventional power-pop electric guitar, bass and drums. Drop those country instruments, up the tempo a bit and add more of a whine to the vocal and you could have a pop-punk song, right?
That’s exactly what The Dollyrots heard in it and how they covered it. Lead singer Kelly Ogden has the perfect pop-punk balance between a whine in the chorus and a more melodious voice in the chorus. And the band nails everything else: the crunchy guitars, the power in the pop, the double beat in the break near the end. The Dollyrots make it sound like “You Belong With Me” has always been a pop-punk song. — Riley Haas
12. Christian Lee Hutson — Betty
The vibe on Christian Lee Hutson’s cover runs heavily toward the Sam Beam / early Iron and Wine end of the sonic spectrum. Elliott Smith is another obvious influence. And yet Hutson’s broody Americana atmosphere suits his interpretation of “Betty.” The switch to a male perspective works well too, changing the story’s emotional resonance. Not sure which is better, “Betty,” or Hutson’s take on Abba’s “Dancing Queen.” Both songs are on the artist’s Version Suicides EP (Vol 1) released in 2021. — Tom McDonald
11. Pendulum — Anti-Hero
Pendulum took to Australian radio station Triple J in 2023 to show the audience a live version of Taylor Swift’s “Anti Hero.” The original Midnights hit was first released the year prior. With the five-piece’s grimy, electronica-meets-alt textures and riveting bass-and-percussion, this version of the song is like nothing else. The band said in the interview which followed, “We’re Swifties!” and joked about helping her with exposure, chart numbers, and selling tickets.
They tried many different things with the cover, but ultimately attributed the drum and bass tempo as the element main that led to the song coming together. The harmonies? Soaring. The percussion? A pulsing, irresistible breakbeat. What was once a synth-pop hit has now turned into a live dark, grooving anthem. — Aleah Fitzwater
Great list – I had only heard one of these before. (Also, the “glitch” on her website a month ago now looks to be having its payoff, so good timing with this post!)