15 Music Writers & Musicians Share Their ‘Favorite Moments in Rilo Kiley Songs’

A couple of weeks ago Tao Lin asked my twin sister to edit a list of musicians and writers discussing their “favorite moment in a Rilo Kiley song.” She couldn’t do it because she was going on a yoga retreat. (Om.) She asked me if I would do it even though she knew I was also going to be on vacation this week. I did it anyway, I guess because I have a better work ethic than her or whatever.

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“Pictures of Success” has always been my favorite Rilo Kiley song. I listened to it on repeat as a high school student on Long Island; scribbled its lyrics into my notebooks and AIM profiles and away messages. “They say California is a recipe for a black hole / And I say I’ve got my best shoes on, I’m ready to go.” I never wanted to move to the West Coast, but I badly wanted out of the suburbs, to move to the city even though I knew it was sort of bad for me. It always felt relatable. It’s resonating particularly strongly now: I’m writing this from California. It’s my first time is Los Angeles. A bunch of my friends in Boston are moving here in the fall. I’m leaving Boston too, for New York, I think. I always come back to “Pictures of Success” when I’m leaving places. It makes sense. Recently I realized that I relate to Rilo Kiley lyrics more now, as a 23 year old than I did when I first discovered The Execution Of All Things as a teenager. It also makes sense; Jenny Lewis was pretty close to my age when she wrote these songs. I think this has been happening for a lot of people around my age who were Rilo Kiley fans in high school.
Liz Pelly, writer/editor for Stereogum

There is a song called “Jenny You’re Barely Alive” that is on a Saddle Creek compilation album called “Saddle Creek 50.” I remember listening to this song over and over after I first heard it, because it was a lot "weirder" and darker than any of the other Rilo Kiley songs I had heard to date. There is a part in the song when Jenny Lewis says “The metal rods you put in your fucking jaw To keep you from grinding your teeth every night” and it’s like the most badass thing ever. I remember driving on the 2 freeway in Glendale listening to this song over and over and always going back to that part because it was so cool to hear her screaming these insane lyrics when I was so used to hearing her sing all these sweet lyrics in this beautiful Jenny Lewis voice. It’s just a really intense moment in the song and I feel like it captures the mood perfectly- definitely still one of my favorite Rilo Kiley songs to date.
Bethany Cosentino, Best Coast

Once, at that Animal Collective Guggenheim installation, a girl I used to date slapped me in the face really hard and a bunch of strangers gasped. That basically explains the feeling of those upbeat impacts on the chorus of “Portions for Foxes.”
Dale W. Eisinger, writer

I was a serious Saddle Creek fangirl in the early 2000s and remember getting 'The Execution Of All Things' and Cursive’s “The Ugly Organ” and some Bright Eyes single in the mail around the same time. I had also just gotten a 3-cd changer, which for me was a huuuuge deal, so those three were kinda on repeat for months while I did math homework. "Paint's Peeling" was my favorite from that album. The guitar work is subtle and ominous, and covers a lot of ground going into the bridge–where Lewis is singing, "last night when my hands were choking you." After that it just explodes with guitars and distorted telephone vocals. I also like all the songs Blake Sennett sings.
Sadie Dupuis, Speedy Ortiz

When you’re caught up in a feedback loop of anxiety and self-loathing, there are very few things that can slap you into being a person again. One of them is Calming Manatee. The other is Jenny Lewis, methodically building up a life size dummy of your sorry state as only someone who's been there can accurately replicate, then smashing the shit out of it. At the moment Lewis screams, "Sometimes when you're on, you're really fucking on," over swelling marching band drums, like some sort of wizened bipolar lieutenant leading you to battle against anxiety monsters, she makes you really believe you might win. (And then there are victory trumpets.)
Nina Mashurova, writer

My favorite moment in a Rilo Kiley song is in Spectacular Views" from The Execution of All Things. I love when Jenny sings the line “you never knew why you felt so good in the strangest of places like in waiting rooms, or long lines that made you late, or mall parking lots on holidays.” It reminds me of being mentally able to overcome the annoyance of doing things you don’t want to and allowing yourself to be happy in spite of what you're physically doing.
Laura Catalano, Weed Hounds

It is fitting that my first boyfriend introduced me to Rilo Kiley-his family life was filled with enough melodrama to perfectly inspire a Lewis/Sennett collaboration. With my hair the same shade of strawberry as Jenny’s signature locks, I soon found myself obsessed with the words pouring out of her mouth. Trying to explain the effect Jenny has had on my life seems futile and silly-the woman practically raised me. I blame her for my overtly emotional attitude and my need to “choose sadness” even if it “never once has chosen me”. My favorite Rilo Kiley song has always been “Does He Love You?” I can vividly remember driving to Best Buy after high school ended and buying a copy of More Adventurous. I can also remember the first time I heard track two- in true suburban fashion, I was sitting in the parking lot of a pet store. The whole thing just hit me, hard, and I could hardly believe a song so perfect could exist. I daydreamed of going to California, of seeing the things Jenny saw, in a blissful seventy-five degree backdrop. How a sixteen-year-old girl was able to relate to a song about adultery is beyond me. All I know is that when Jenny screams “I am flawed if I’m not free”, my heart still gives in every time.
Rachel Gagliardi, SLUTEVER

“My favorite moment in a Rilo Kiley song is ‘A Man/Me/Then Jim’, where she starts with ‘I had one friend in high school recently hung himself with string. His note said, if livin is the problem, well that’s just baffling.’ Wow.”
Faye Orlove, writer/artist

"Does He Love You?" has always stood out as one of my favorite Rilo Kiley songs, a shining example of Lewis' ability to deliver earnest emotions. The climatic end reveals a heartbreaking love triangle between the narrator, the friend she's writing to and her husband; a tale that sounds like a bad plot in a soap opera, but is executed perfectly without an overwhelming sense of melodrama …Who needs to watch the Young & the Restless when you can just listen to this song on repeat instead?
Melody Lau, writer

I think my favorite moment in a Rilo Kiley is in “The Good That Won’t Come Out (Execution of All Things)” when she says “as we watch it melt” after referencing her friends talking about the disappearing ground. I think I was 15 when this album came out, and I was starting to get hardcore into awareness of environmental issues, so that lyric has always resonated with me. That whole album has a lot of lyrics that got me through my formative years and helped me through “becoming an adult” (am I there yet?).
Mallory Hestand, Earthquake Party

During my first few months of college, I set “The Execution of All Things” as my alarm, so the first few bars of that song’s intro are particular favorites. That tick-tocking, violin-marching crescendo is still lodged in my brain as this beautifully optimistic, brand-new-start, be-whoever-you-want-to-be sunrise, even when the lyrics that follow them are so anxious: “Soldiers come quickly/I feel the earth beneath my feet.”
Devon Maloney, writer

“Jenny Lewis was my first alt-girl crush. This was before realizing I probably liked boys too, and maybe the fact of her dating Conor Oberst was enough to project a cult-like obsession for the whole Saddle Creek clique. By college, the dream of Omaha faded fast. But Rilo Kiley came back in a big way, with Under the Blacklight staging the soundtrack for my own twentysomething “Great Sexual Awakening.” ‘Moneymaker’ is the kind of song you can get down to when trading awkward hookups for places to stay in cities you’ve always wanted to see; its shamelessly surface lyrics, the porny guitar riff, Lewis’ breathily orgasmic ‘out out out, ohh yeahh’ capture some of the weirdness of semi-transactional sex . I feel pretty okay about it now.”
Chris Lee, writer

“I have a really vivid memory of pulling into the driveway with my mom at thirteen and asking her to listen to ‘Does He Love You?’ I gave her my earbuds and about halfway through she started to cry and we held hands. Getting misty thinking about it. I also remember hearing that story about Jenny Lewis recording ‘I Never’ naked for the first time and then going home and belting it in my undies before bed. I cannot believe I was 13 when that record came out, v formative for me.”
Johanne Swanson, Yohuna

Probably the first real “indie rock” concert I ever attended was Rilo Kiley, opening for Elliott Smith, at the Henry Fonda theatre in LA, February 2003. I was 18. It was also my introduction to the band, and the only emotion I can remember feeling is shock–they were so direct, unvarnished, honest. Elliott Smith (my gateway drug, i was completely obsessed) had these qualities too, but the way Rilo Kiley transmuted them to a live rock format was entirely new to me. I can’t clearly remember one song from that night, but I did pick up “The Execution of All Things” and the rest of their discography followed. “Picture of Success” always perfectly captured the R.K. spectrum of feeling for me–Jenny Lewis’ vocals growing from soft spoken, sweetly sung emo-kid poetry to that tough, triumphant chorus, “ready to go.”
Dylan Travis, Some Ember

Every time I am driving on tour and see the number 16 on one of those mile markers that tells you how far you are from your city, I put “With Arms Outstretched” on and scream ITS 16 MILEEEEES TOOOO THE PROMISED LAAAND. That always will be my favorite Rilo kiley moment.
Cameron Potter, Little Spoon

The part in The Execution of All Things when she says ‘I do this thing where I think I’m real sick/but I won’t go to the doctor to find out about it/cause they make you sit real still in a real small space as they chart up your insides and put them on display / they’d see all of it all of me.’
Jenn Pelly, staff writer at Pitchfork TC mark

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