On their remarkably self-assured 1999 debut, the indie rock band were already in possession of the wry, morbid sensibility that would define them.
Before she was one of the most beloved singer-songwriters of her era, Jenny Lewis was best known for her role as redhead girl scout Hannah Nefler in the 1989 film Troop Beverly Hills. While she was able to indulge in some of the trappings of child stardom, Lewis’ youth was anything but glamorous: She carried an immense pressure as her family’s breadwinner, which was made all the more difficult by her mother’s struggles with addiction. In the mid-’90s, when a teenage Lewis met Blake Sennett, a fellow young actor with credits on Salute Your Shorts and Boy Meets World, they recognized each other as kindred spirits, both disillusioned with showbiz and its associated pressures. “I was incredibly depressed, having grown up doing one thing and suddenly finding myself not interested in that,” Lewis told Spin in 2007. “I really had no idea what I was going to do with my life.”
For both Lewis and Sennett, music was an opportunity to explore creative autonomy; for the first time, they were pursuing their own visions rather than acting out someone else's dreams. (As Lewis’ sister recently told Pitchfork, “I think she didn’t want to be saying other people’s words anymore.”) Lewis and Sennett sat down to write songs together and soon were playing casual shows in their friends’ living rooms; later, they started dating. Somewhere along the way, the band formalized under the name Rilo Kiley. Sennett recruited his high school buddy Pierre “Duke” de Reeder to play bass and Dave Rock to play drums, a role that Jason Boesel later settled into.
In January 1998, Rilo Kiley played their first show at a Silverlake nightclub called Spaceland. If they were nervous, it didn’t show. “Between songs they were charming, smart and funny,” recalls The Kids in the Hall comedian Dave Foley, who happened to catch the set. “During songs they were brilliant.” Smitten, he offered to pay for a demo recording, which the band accepted. Many of the songs from the Foley-funded session would go on to form Rilo Kiley’s self-titled 1999 debut (later released with a slightly altered tracklist as The Initial Friend EP).
For two songwriters who grew up surrounded by Hollywood fakery, Sennett and Lewis’ songwriting is immediately, remarkably unselfconscious. Their twangy indie rock songs avoid flowery language in favor of conversational observations and winking wordplay. “I should’ve known/With a boy like you/Your middle name is always/I’d always love you,” Lewis swoons on a synth-pop ditty called—obviously—“Always.” Same deal with “I’ll be in your car/I locked the keys in your car/I’ll be in your car for now” off “85.” Perhaps there are more poetic ways of expressing these sentiments—of fateful infatuation, of resolve—but the directness of Rilo Kiley’s storytelling aims straight for the heart.
Lewis’ emotional candor, along with the band’s association with Conor Oberst and Omaha label Saddle Creek, have led some to describe Rilo Kiley as emo, a genre most commonly linked to whiny, vaguely ill-looking white boys. There are arguments to be made for both sides of the emo-or-aren’t-they question, but it is incontestable that Lewis’ capacity for vulnerability spoke to countless young women. Her expressions of sadness could take many shapes—wry, morbid, exhausted—but were always excruciatingly self-aware and sharp. “I’ve been a mess for some time now/I get what I deserve,” Lewis sings on “85.” “For someone who leaves a lot behind/I can do better.” On the pop-punk-lite “Glendora,” Lewis describes her own exploitation at the hands of a cruel boy who uses her for sex and a distraction from suburban malaise. “You know I always like to play the victim,” she sings plainly. “And would you fuck me? Because I’d fuck me.” It’s a disarming line, and “Glendora” lays the contradictions of womanhood out on the table, a whole bundle of flaws and strengths tied up in one complicated package. “When I sit down to write a song, there is no filter,” Lewis told ELLE years later. “I’m not trying to write for anyone or anything specifically. It’s just trying to capture a little piece of your soul—even if it’s a really ugly part.”
Though Rilo Kiley is rooted in indie rock, it’s clear that the band had not yet found their sound. The Sennett-led cut “Asshole” is broken up by turntable scratching and samples while Lewis straight-up yodels on “Gravity.” On “Teenage Love Song,” an aching Patsy Cline-indebted ballad, Lewis two-steps her way towards the tortured melodrama of a broken heart. “Oh Davey, why did you leave me/All alone when we went all the way?” she belts like a gale-force wind roaring through Nashville. “But maybe someday Davey/We’ll be together for more than a day.”
And then there’s “The Frug.” Despite the fact that they were unsigned, Rilo Kiley’s music made its way into the hands of director Morgan J. Freeman, who included two of the band’s songs in his 1998 film Desert Blue. Freeman’s video for “The Frug” landed the band on MTV’s alternative program 120 Minutes. It was a bit weird for everyone. As Sennett recalled in 2001, “It’s pretty random to see the most independent of independent bands on MTV.” Filled with handclaps and doo-wop harmonies, “The Frug” is one of Rilo Kiley’s sugariest songs and is unlike anything else on Rilo Kiley. As the song patiently explains, Lewis can do the Frug. She can also do the Robocop and the Freddie. She cannot do the Smurf. But this groovy laundry list gives way to a declaration of strength and empowerment: “I can take my clothes off/I cannot fall in love/You will never see my eyes/I will not call you back.”
After the release of Rilo Kiley—sold exclusively at their shows—the band spent the next few years searching for a label before signing with Seattle’s Barsuk and releasing their proper debut, 2001’s Take Offs and Landings. That same year, Lewis and Sennett split and songwriting responsibilities started to shift over to Lewis. Rilo Kiley’s final record and major-label debut, the sleek and divisive Under the Blacklight, came out in 2007. By that point, Lewis and Sennett were both branching out with side projects (Lewis’ solo work, Sennett’s band the Elected) and interviews with the group from that time suggest that Lewis’ independent success drove something of a wedge between the pair. When asked about the status of Rilo Kiley in 2011, Sennett said that if the band were a human, “he’s probably laying on his back in a morgue with a tag on his toe.” A few years later, Lewis drove the final nail into the coffin and confirmed that Rilo Kiley was no more. Since then, with only a 2013 rarities set to tide fans over, the band has existed as a treasured manifesto on how to live a truthful, if imperfect, life. If the breakup was a song, Lewis would probably point out that it was better that way.
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