Rilo Kiley, Jenny Lewis, Taylor Swift, And The Trail Of Heartbreak Pop

By Tatiana Tenreyro


Rilo Kiley came into my life any time Whenever I was 16. I couldn't have noticed the California indie-rock musical group at a more pivotal time. At that age, I was dealing with two terrible relationships continuous that broke my spirit, while also feeling like an outsider in high school. Jenny Lewis's songwriting helped me find solace; her songs made me feel like she was the cool older friend guiding me through it all, validating my emotions, with songs like "Capturing Moods," "Go Ahead," and "Glendora."


Although for the other teenage women I knew, the musical icon they related to the most was Taylor Swift. At the time, I wrote off Swift, focusing on her imperfections. Her songs comparing herself to the popular cheerleader and wanting a fairytale romance felt infantile, and the slut-shaming in "Better Than Revenge" made me uncomfortable.


Although four years back, I started to notice that Swift and Lewis have far more in normal than a certain ex. In 2016, I stumbled upon a playlist Swift made for iTunes from 2010. It's no longer obtainable online, although it features Rilo Kiley's "Silver Lining" off the band's last album, Under the Blacklight. It's a ballad about finding strength in leaving in back of a unhealthy relationship. Whenever I found the track in the playlist, everything clicked.


Before Swift emerged because the queen of lovelorn songs, Lewis was telling stories with Rilo Kiley in the same vein. As soon as the musical group emerged with its 1999 self-titled debut EP, often known as The Beginning Friend — getting a vinyl release and its streaming debut today (October 2) — Lewis introduced the musical group as one that would soundtrack teenage woes. The EP was made soon following the musical group made its debut onstage in 1998 at L.A.'S now-defunct DIY venue Spaceland. The Kids in the Hall star Dave Foley happened to be in the audience and was so amazed by their set that he insisted on funding their debut EP.


At the time of writing the record, Lewis was just 21: young enough that she may pen songs that'd make teenage women feel seen, although old enough that she may analyse who she was throughout her teen years from a detached lens. The lyrics feel like a diary entry, raw and emotional, without holding back on revealing her vulnerability.


Having experienced fame at a young age as a child star, appearing in Troop Beverly Hills, The Wizard, and other late '80s and '90s staples, Lewis was well aware of what it seemed like to date prominent males with big egos. One of the most recognizable songs off Rilo Kiley's debut is "Teenage Lovesong," about Lewis falling in love with a famed boy named Davey (speculated to be Married... With Children's David Faustino) and losing her virginity to him, only to have him ditch her. There's "Teenage Lovesong" DNA in Swift's iconic "Fifteen," whether it's intentional or not. Though the song was written long before Swift started dating well known gentlemen, "Fifteen" tells the story of her best friend Abigail, who lost her virginity to an insensitive teenage boy who acted eerily similar to Lewis's "Davey."


Although the song that every Rilo Kiley fan understands off the band's debut is "Glendora." It features some of Lewis's rawest songwriting, detailing the several ways that the guy she's crushing on mistreats her. She acknowledges that she should find someone better for her, although she just cannot seem to drop him. I think of Swift's "We Are Never Ever Getting Back Together" as "Glendora"'s sister song, with the former finding has Swift noting how hot and cold their relationship is. While Lewis takes a more self-aware approach, pointing out that she can't help victimize herself, Swift sings about being prepared to move on, cut ties, and not fall for the same trap again. Swift's song is famously purported to be written about Jake Gyllenhaal, who also dated Lewis and remained companions with her soon after their relationship ended back in 2001. (Though it's rumored that Swift wasn't happy that Gyllenhaal asked Lewis, his ex, to be his date to the Golden Globes in 2011, Lewis clarified in a tweet that she was already dating Johnathan Rice at the time.)





Swift's approach to writing breakup songs also feels reminiscent of Rilo Kiley's "Portions for Foxes," off their third record, More Adventurous. Back in 2008, former USA Today reporter Brian Mansfield had then-18-year-old Swift import the information from her iPod Nano into a flash drive for an interactive feature on what she was listening to, including “Portions for Foxes.” The song came out just two years before Swift debuted as a rising country-pop star with her self-titled record, also it carries the same weight as her breakup anthems. Lewis sings about a relationship falling apart immediately after a partner's infidelity. His wandering eye is set on a "pretty young thing," although Lewis can't with little effort get rid of her feelings for him. I like to imagine teenage Swift listening to "Portions for Foxes," finding as much solace in it as I did.


However surprisingly, while Swift’s and Lewis's approaches to songwriting are similar, their careers went in opposite directions. Lewis, who'd been in the limelight since the early '80s, became an indie darling rather than an arena pop star. With Rilo Kiley, her work with the Watson Twins, and even her stint in The Postal Service, she primarily focused on indie-folk without totally exploring the pop realm up until Under the Blacklight. Swift, on the other hand, has never concealed her love for indie, however didn't experiment with a more indie-folk sound up until Lover. This year's Folklore became a homage to the indie-folk that Swift's been a longtime fan of, with The National's Aaron Dessner as co-songwriter and producer. She also includes Lewis's friend and collaborator, Bon Iver, on "Exile."


Though Lewis herself isn't present on the album (even though it would've been a brilliant match), you could still hear hints of Lewis's influence on it. In a way, Folklore is Swift's More Adventurous, Rilo Kiley's 2004 lush folk/country album. It's heavily acoustic, featuring Lewis's most elaborate songwriting. Lewis introduced new characters who aren't herself in songs like "A Man/Me/Then Jim" and "Does He Love You?," While still making the album feel like a relatable gut punch.





The same can be mentioned for Swift's Folklore. Swift has habitually excelled as a songwriter, being one of the few huge pop stars who primarily writes on her own, although the lyrics on Folklore are her most fancy nevertheless. Swift's songs often feel confessional, with fans speculating about how they tie into her personalized life, although Swift shifts away the focus from herself for segment of the record onto a fresh crop of characters. There really are three songs, "Cardigan," "August," and "Betty," focused on a teenage love triangle, and there's a revenge ballad about a maligned widow angry Woman"). Like More Adventurous, it's stripped down, allowing the acoustic guitar and piano to shine rather than relying on Auto-Tuned radio-friendly pop. Folklore is different from anything Swift's done before, nevertheless it still feels so inherently her.


Their careers could not be more different – hell, Lewis was supposed to be opening for Harry Styles this year on tour – although through Rilo Kiley, Jenny Lewis set the blueprint for who Taylor Swift became to a new generation of young adults who sought to be reminded they're not alone in their struggles.