Why I Needed Jenny Lewis

The first in new series of essays

Meg Brennan
8 min readFeb 12, 2023

It’s only proper that, when tracing the influences for this series, I start with the music that pierced me as a teenager. I don’t think there’s a more intimate relationship than that of a teenage girl and her headphones; and though mine were blasting a typical mix of suburban malaise, none rang better in my ears — and still does — like the songs of Rilo Kiley, particularly those written and sung by Jenny Lewis.

I first heard Rilo Kiley on a burned CD playing on my friend’s walkman that we shared on the bus to school. The album was The Execution of All Things, and the songs might’ve be out of order (in one instance “With Arms Outstretched” cut off after a minute, and I wouldn’t hear the entire song for some time), but it began appropriately with “The Good That Won’t Come Out.” A light tap of a song, Lewis’s singing almost a whisper throughout, as though conferring with me in secret. “You say I choose sadness, that it never once has chosen me.” she sings, honest and resigned.

I won’t pretend to be a good enough historian to explain how this moment came to be in alternative pop music, how Lewis, with her southern California child actor background, was perfectly suited to explain a sort of gilded malaise that existed in the early 2000s in middle class communities like mine. Ours was a mid-Bush years, post-Columbine world, where we benefitted from a status quo that nonetheless rankled us, not yet online enough to organize our thoughts outside of LiveJournal or MySpace. As always, it was a time of creating identity and forging belonging, and when I found myself adrift — not pretty, not straight, not naturally happy — Rilo Kiley was there for me to provide some vessels that would fit my self-perception.

It wasn’t just Lewis’s songs, of course — other Saddle Creek recording artists spun regularly: Bright Eyes, Tilly and the Wall, Cursive. When listening to a radio broadcast from Seattle I discovered Death Cab for Cutie and, by extension, The Postal Service. From the UK we had The Smiths and Belle and Sebastian. Boys at parties knew how to play “In the Aeroplane Over the Sea” and “The King of Carrot Flowers” by Neutral Milk Hotel. Some of these seem silly or grating now, some have grown deeper with time. I won’t say which.

But Jenny Lewis kept making music after The Execution of All Things, just as I kept on through high school, then college, then young adulthood, these albums becoming earmarks in my life.

First, there’s the matter of her songwriting. I’ve already hinted at melancholia, but I do not mean that in terms of hopelessness; rather, Lewis always seems to write from a place of understanding, whether removed or retrospective. Something tragic may have happened — lost love, a wasted youth, the death of a friend, the disillusion of family — but it has happened, as a part of life, and acceptance and understanding always follows. Lewis’s protagonists are never tragic to the point of destitution, rather, they are taking the blows and promises of life as they come, with one foot out the door, hoping for the best while anticipating the worst.

A perfect example of this is one of Rilo Kiley’s most enduring songs from The Execution of All Things, “A Better Son/Daughter.” The lyrics open from a first-person perspective, as sung by Lewis:

Sometimes in the morning I am petrified and can’t move,
Awake but cannot open my eyes
And the weight is crushing down on my lungs, I know I can’t breathe
And hope someone will save me this time

The physical description of depression is relatable enough, which is why the second verse makes a small, masterful shift:

And your mother’s still calling you insane and high
Swearing it’s different this time

The point of view changes, almost as though saying “I experience troubles in my life. And so do you. In this, you are not alone.” The final verse delivers the final note of this message, that you will be okay.

And sometimes when you’re on, you’re really fucking on
And your friends they sing along and they love you
But the lows are so extreme, that the good seems fucking cheap
And it teases you for weeks in its absence

This part of the song is not in Lewis’s usual detached voice, but shouted, like a cheer from the stands: sometimes things are good. Sometimes things are terrible. You will be okay.

I can, of course, only speak to my feelings as they were in my middle-class suburban upbringing. I find it disingenuous to do anything else, especially in a piece like this. I recognize that for other experiences the message of “you’re going to be okay” might seem trite, the troubles of being too sad to get out of bed extraordinarily trivial. I mulled these truths over and over when deciding whether or not to write about Jenny Lewis. Shouldn’t I, An Intellectual, be speaking on artists and writers whose perspective opened me to more marginal existences, expanded my worldview and pulled me away from the white, buttoned-up existence that I was all too used to?

Perhaps. But that is not what this essay, or many on this topic, is made to do. I am not here to share my bona fides on the best music, writing, etc. to have existed, there are wiser and greater minds than mine that have already done so. I am not here to explain what art the world needs, but what I have needed in my life, the bricks that built me.

I say this now because the idea of honesty about oneself and one’s position feels intrinsic to Lewis’s songs. They do not feel maudlin or boring enough to be confessional, nor do they feel grounded enough to be slice-of-life storytelling. And yet they convey a philosophy of the self, of how to conceive yourself while moving through life.

You can see this on “More Adventurous,” the title track from Rilo Kiley’s next album (which I blew off for a while, thinking that they had “sold out to a major label.” I was 16):

And if my brain quits
Well I guess then that’s just it
And if my hands stop workin’
You can call me lazy
And if I get pregnant
I guess I’ll just have the baby
Let it be loved
Let me be loved

Elsewhere on the album Lewis’s stories are truly tragic: the ruined friendship in “Does He Love You?” pits caution against indiscretion, “A Man/Me/Then Jim” shows how disparate human beings are bonded by the universal cruelties of life, what she calls “the slow fade of love.”

Acceptance doesn’t feel like the exact word for this sentiment. Lewis’s lyrics aren’t passive or nihilist, they are observant, shrewd, and honest. “The absence of God will bring you comfort, baby” she says, gently removing an almighty to rage against. And, at the end of the album,

This loss isn’t good enough
For sorrow or inspiration
It’s such a loss for the good guys
Afraid of this life
That it just is
’Cause everybody dies

Rilo Kiley split, and I went to college. Jenny Lewis went solo with the twangy Rabbit Fur Coat, the theme of self-acceptance maintaining itself in a tired, growing-pains way:

I’m fraudulent, a thief at best
A coward who paints a bullshit canvas of
Things that will never happen to me

My family left the suburbs in Florida for the neighborhood of Portland, I lived in Vancouver and then England and came to Portland for what was supposed to be a year and became fourteen. I wasn’t a teenager, I liked music for aesthetics, for moments of beauty, but no longer for the ability to sink its fingers around my heart like when I was fifteen. Jenny Lewis released another album — Acid Tongue — which felt like a departure from what I’d loved so much years before. I replayed The Execution of All Things and felt that was all had, and it would be enough.

On August 16, 2015, I was riding my bike to work. There was hardly any traffic, a perfect Sunday morning, and as I zipped around the corner another cyclist appeared coming toward me, in the middle of the bike lane, on a collision course. I squeezed my brakes and when my bike screeched to a stop I kept going, sailing over the handlebars, landing on my elbows, then my chin, then my head.

I needed seven stitches in my chin. My right eye was black, my elbows scraped raw and nearly torn from bracing the weight of my body when I fell. I went home, my body shaking and tired with trauma. I had tickets that night to see Jenny Lewis that night. I called my mother, who was going with me, and told her about the accident, that I was okay, but in a lot of pain, and not sure that I could stand for a few hours in the cramped, dank space that was the Crystal Ballroom downtown.

“Okay,” she said. “You think about it, and let me know. Please get some rest.”

I put on Lewis’s latest album, The Voyager.

There’s a little bit of magic
Everybody has it
There’s a little bit of sand left in the hourglass
There’s a little bit of magic
Everybody has it
There’s a little bit of fight left in the end

I called back. Of course I would go.

The show was perfect — I found a bench to stand on above the crowd to keep my tender elbows safe, she played the hits, finishing her set with “A Better Son/Daughter,” a song that had, by then, become an anthem in my heart. For her encore, she played “Acid Tongue,” a song I didn’t know well because, as noted above, I hadn’t liked the album at first.

The song itself is acoustic, almost acapella: Lewis and her band clustered around a single microphone.

To be lonely is a habit, like smoking or taking drugs
And I’ve quit them both, but, man, was it rough.

Here, over a decade since “The Good that Won’t Come Out,” was that same lesson: life will be difficult and it will be beautiful, and you can get through it. You know you can, because you already have, and man, was it rough — but sometimes when you’re on, you’re really fuckin’ on.

Further reading

If you’re interested in listening to Jenny Lewis’s music, starting with Rilo Kiley is the best move — I will, of course, recommend The Execution of All Things and More Adventurous, though Under the Blacklight and Takeoffs and Landings have some amazing content. Of her solo work, I would say that The Voyager is her best, though On The Line is spectacular. I’ve also put together a playlist of some of my favorites, some discussed here and some not, that serves as my introduction to her songwriting. Apologies if you’re a Spotify purist.

As a final note: I know that I hardly spoke to Jenny Lewis’s own biography, though it is fascinating in its way. I would recommend this profile in American Songwriter to start.

And, if you needed an excuse to rewatch Troop Beverly Hills, here it is.



Meg Brennan

I write thinkpieces about theme parks and lists of things that aren’t related to theme parks. You can find my older posts on my Substack here: https://parksandc