An Extremely Personalized Playlist of Jenny Lewis, Patron Saint of Self-Important Sad Girls

Or: an essay meant to exorcise from myself the urge to get Jenny Lewis bangs again.

Before the latest astrology resurgence made it common practice to compare birth charts prior to scheduling a date, I only cared about my zodiac sign—Capricorn—because it is Jenny Lewis’s, too. To my mind, somewhere back inside the foaming battlegrounds of tenth grade, this coincidence reformed into a sacred bond, a long silver string stretching across the country to me from California. I don’t know; it felt true. Though I’ll now concede Lewis has not, in her solo work or the records released by her 2000s band Rilo Kiley, been dedicating her efforts to me personally, her songwriting does thread the needle between vanity and introspection in a manner so singular, so striking, as to be catnip for the type of self-important sad girl inclined to make that kind of assumption. If that sounds like a dig, it’s only at me. No one examines the bruised-plum soft spots of womanhood with a more clear-eyed sigh—at once cool and contemplative—than Jenny Lewis.

Lewis’ new album, On the Line, is grand and entrancing, a wry solo masterpiece that tells intimate tales of loss with nimble, hard-won confidence. Always a chronicler of artifice, finding the roiling blood under the sequins, this spangly singer-songwriter triumph catalogues personal pain, the detritus and decay that is an inevitable side effect of existing, and lays it bare using a broad variety of sonic styles—from canyon rock to folk pop to piano ballad and more—that’s in dialogue with the whole wide and ancient tapestry of human storytelling. (Also occasionally, it recalls Carole King’s Tapestry.)

No one examines the bruised-plum soft spots of womanhood with a more clear-eyed sigh than Jenny Lewis.

I cried into a plastic cup of fruit over it at the park and scared some teenagers. Later that day I wrote an email to a girl I used to kiss and haven’t seen in a year, my tone uncharacteristically buoyant, refreshed. I wanted her to know about the Meryl Streep line in “Party Clown.” Running in my neighborhood while listening again, I thought light should be shining out of my pores, as huge and phosphorescent as these songs made the center of me feel, and I somehow vaguely hoped somebody would stop on the sidewalk and thank me for what my move to Los Angeles last year had clearly wrought. The city’s bangs-clad bard, back again.

An annoyingly self-fashioned Silent Generation stoic, I have never liked admitting that anyone’s influenced me at all, preferring to imagine I sprung fully-formed from the earth, equivocating and wearing chambray—but there’s no denying the impact of Jenny Lewis in my life. “Formative” feels insufficient, a term to apply to a childhood crush. Lewis’s voice is the one I was listening to, her words in my head—one of the first, and few, female ones—during periods where I was most actively constructing myself into the person I might want to be, or some acceptable facsimile.  

In that way, these selected Jenny Lewis tracks constitute a tour of one of the longest relationships in my life. These songs scored so many moments of willful disaster that they became almost co-conspirators in my unhappiness, implicitly sanctioning whatever hurt I sought out, making it clever, attractive, twistedly empowered. I find On the Line heralds a separate era entirely: doing honor to the darkness that encroaches at the corners without luxuriating in it, walking forward, more sure-footed now.

“The Absence of God,” More Adventurous (2004)

It is September and I am wearing a red soccer uniform at a record store with my aunt. She leaves me holding her coffee to run and put money in the meter, so I pretend I am out shopping alone. I lift a copy of Rilo Kiley’s recently released More Adventurous off a New Releases display and a clerk in a flare skirt with a strip of exposed skin around her waist leans across the counter and says, “The lead singer of that band is a girl, you know?” I didn’t, but because I am twelve, or because I am a massive, natural fake, I nod gravely. Of course. This record store creature—who, viewed from a distance, was definitely younger than I am now—seems incredibly sophisticated, so she gets my babysitting money and I get Jenny Lewis and that’s that. A year later, when the album’s biggest hit “Portions for Foxes” was used in the first episode of the ninth season of Grey’s Anatomy, I knew the song and my mother did not, which felt a more certain marker of becoming an adult than menstruation, or confirmation, or turning eighteen.

More Adventurous is also an important record for me because it served as a bonding point with a friend’s cool older sister who I was so obsessed with that I attended a high school production of Grease twice in one weekend of my own volition. “The Absence of God” is an important song, broadly, because “And I say there’s trouble when everything is fine / The need to destroy things creeps up on me every time” locates sensitivity and violence as kissing cousins, or at least, forces we employ against ourselves in tandem to undermine our best interests, shouting “fire” in the theater of our skulls. This song taps into that impulse to veer the car toward the abyss just because it’s there, because those are your hands on the wheel, so you can. There is an argument to be made that “And I’m not my body / Or how I choose to destroy it” was the jumping-off point for the very bad body horror poetry I wrote and, as editor-in-chief, saw fit to proudly publish in my high school’s lit mag, and for that I owe many apologies, but I think having a first big existential crisis about what constitutes the Self way before Instagram, or even college, worked out okay in the end.

“Glendora,” The Initial Friend EP (1999)

I first heard “Glendora” on MySpace while looking for a Rilo Kiley track to set as my profile song so everyone would know I was interesting, thoughtful, and deep. At one point, I used “Handle with Care,” the (excellent) Traveling Wilburys cover that appears on Jenny’s first album, Rabbit Fur Coat, and includes features from Ben Gibbard, Conor Oberst, and M. Ward because, I guess in the interest of getting a prom date, I also wanted everyone to know I liked trembly white boys. “Glendora” recounts an unfortunate New Year’s Eve. It perfectly distills the volatile restlessness of being young and hungry—for sex, shame, sundaes.

As written and sung by Lewis, the narrator of “Glendora” voluntarily subjugates herself, and knows it. “You know I always like to play the victim” she seethes, wise enough to be perfectly aware she’s electing mistreatment (“They make me sick, you make me sicker / But I want to please you, so I go and I get with her”), to smirk, then acquiesce anyway. The straightforward sketch of the experience of accepting, even courting, careless and cruel people into your orbit just for the body closeness, for something to do, was revelatory to me, and the song was among my most treasured during the years when I couldn’t stop myself from doing the same. In an interview in 2014, Lewis expressed embarrassment about this early track, and the sentiment is easy to understand. While I am grateful to have “Glendora” as an ode to a piece of myself that I’ve since more or less wrangled under control, I’m even more grateful that my own smutty juvenilia has been mostly scorched from the earth.

“The Good That Won’t Come Out,” The Execution of All Things (2002)

The single most culturally significant bridge in all of music is in “Not Ready to Make Nice” by the Dixie Chicks. The second is in “The Good That Won’t Come Out” by Rilo Kiley. This is evidenced by the fact that it contains the line that launched a thousand AIM away messages, “You say I choose sadness / That it never once has chosen me / Maybe you’re right,”  because actually teen girls are smart and have great taste. No questions, thanks.

“Does He Love You?,” More Adventurous (2004)

Forcibly defiant, but mournful, the words “I am flawed if I’m not free” seem to alight like a brand on my forearm when I hear them. When asked my favorite Rilo Kiley song—I am a woman in her late twenties who had a Peter Pan collar phase, so this happens not infrequently—I always say “Does He Love You?” to establish myself as a chaos agent, but I really am weak for a story-song. Sure, I’ve turned repeatedly to “Does He Love You?” as a commiserating liniment upon emerging wounded from my most fitful, self-destructive choices, but assuming I would have done all those things regardless, at least this track bangs.

“Born Secular,” Rabbit Fur Coat (2006)

I believe that I am the world’s number one “Born Secular” evangelist, a role thematically in keeping with the song’s subject matter. Lyrically spare and searing, it will be most affecting for those who like to get real emo about the concept of “God,” but I suspect even if you are free of that affliction, you will agree that “I was born secular and inconsolable” is a stellar first line.

“Silver Lining,” Under the Blacklight (2007)

“Silver Lining” was playing when I slipped stocking-footed on a mildewed rug while climbing into my not-quite-boyfriend’s empty bathtub to cry about something which eludes me now. Having banged my face on the soap scum-y fiberglass, and newly certain that any bump to the brain would be the one to kill me after actress Natasha Richardson’s death that year, I spent the remainder of the evening stiff as a board in a wheezing brown recliner rescued from the street thinking over the lyrics while a group played poker, which became rummy, which became some stripping-centric version of the drinking game kings. “Silver Lining” made an appearance, stubbornly, on all my playlists back when my chief hobby was cycling rapidly through unpleasant romances I didn’t care about until they’d already ended in calamity. Perhaps I was willing into myself the sense of knowing, righteous grace I heard in Jenny’s voice; I did not feel that I was anyone’s silver lining, let alone gold, but badly craved such a sense of moral victory to arise in me from all this mess. Needless to say, I did not die.

“Late Bloomer,” The Voyager (2014)

Okay, yes, I just enjoy a rollicking, guitar-forward coming-of-age romp with lived-in details about a bisexual threesome. Am I not a being of simple, needful flesh and bone?

“On the Line,” On the Line (2019)

This is an all-time great jam and I will play it at every gathering all spring, all year. I will clasp my hands gently to the cheeks of whomever has the aux cord and tell them not to worry, I’ve got you. I’ve got a doo-wop lovechild of The Beach Boys and The Shirelles for you. I will play it at your party until my hands fall off, or the sun explodes, or they rule music made by women as illegal, and then also after that. The vocals are winsome, the piano swings my heart back and forth like a baby in a pastel electric swing rigged up on the kitchen floor. I let the long dial tone at the end play all the way out every time, superstitiously.

Before I was born, my dad wanted my name to be Caroline, but my mother knew it was more important to pay homage to Melanie Griffith’s character in Working Girl, so he was overruled. There was a year or so in my late teens when I really regretted this turn of events, because the nickname Caro has very gay energy and I thought it was something I could have structured an entire personality around. Now, additionally, I could have been an “eastside girl called Caroline,” but instead I’m just an eastside “On the Line” stan.

“Taffy,” On the Line (2019)

Despite its title, the carnival food which the sensation of listening to “Taffy” most closely approximates is the gauzy spun sugar of cotton candy. Soft and dreamy to the touch, then growing darker, syrupy in your mouth. The song temporarily leaves Lewis’s standard SoCal stomping grounds for midwestern cold and every sound feels delicate—not fragile, but intricate, precise. In relating the sundry details of a waning relationship—the see-through dresses and guilty recon missions into their phone and sex as temporary salve—“Taffy” hits me as something of a spiritual sequel to “Glendora.”

Where “Glendora” has the boldness of a dare, “Taffy” exudes the bravery of making yourself vulnerable. Here, there is the knowledge that giving of oneself does not have to be losing, not some masochistic stunt, but rather an act of making yourself pliable so as to fit with another person, folding into a hope-sick genuflect for love. “I did so freely / I wanted you to see me / Off that throne you put me on” sounds like a prayer and is about sending nudes. The desire is unwavering and plainly expressed. “Taffy” describes heartbreak in a way that shatters, but what lingers is a sense of self-assuredness, firm and calm. “If you’re not willing / Then I’m not giving you my heart of gold” Lewis sings. These most simple lessons can be the hardest to make stick. This one, I’d like to keep. FL

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