Rilo Kiley’s self-titled debut is an early showcase of their vulnerable, sardonic songwriting

Erik Fleming

When Rilo Kiley’s self titled album — also known as The Initial Friend EP — was released in 1999, bandleader Jenny Lewis had already lived a lifetime.

Before she was revered for her evocative storytelling, eye-skimming fringe, and airbrushed pantsuits, Lewis was a child star of the 1980s, appearing in a series of commercials (her first was for Jell-O) before moving onto TV (The Golden Girls, Growing Pains, Baywatch) and film roles (Troop Beverly Hills and Pleasantville). By the late 1990s, her plans had shifted, and she formed the band Rilo Kiley with guitarist Blake Sennett (another former child actor and her future ex-boyfriend), bassist Pierre “Duke” de Reeder, and drummer Dave Rock. Making their debut at the now-defunct Silver Lake rock club Spaceland, in January 1998, the group caught the eye of comedian Dave Foley, who ended up funding their self-titled LP. “Between songs they were charming, smart, and funny,” Foley recalled in a statement. “During songs they were brilliant.”

For the first time in 21 years, Rilo Kiley are reissuing that record, which had previously been available only on CD and sold at the band’s earliest gigs. The album serves as a gateway into their discography, finding the indie-rock quartet at the earliest stages of discovering its sound. Lewis yodels on the chorus of closer “Gravity,” while the Sennett-led “Asshole” is a spaced-out try at psychedelia. On “Teenage Lovesong,” Lewis recalls a kiss-off in a lovelorn country ballad. But together, the duo’s approach is without pretense: They opt for direct lyrics and clever wordplay in favor of poetry, while spotlighting Lewis’s twangy vocals. “I fell in love with you/And don't you think it's sad?/'Cause here we both stand/Amidst the wreckage of our past,” Lewis laments on “Papillon.” And with a wink and a nod on the sparse, synth-pop “Always,” she croons: “I should’ve known/With a boy like you/Your middle name is always/I’d always love you.”

Throughout her career, Lewis has mastered the art of cloaking pain and heartache with sardonic, self-aware songwriting. Rilo Kiley was her launching pad. Take “The Frug,” a depressive tale masked as a darling, hand-clapping ditty. “I can take my clothes off/ I cannot fall in love,” she says. Sex is easy, but love is another beast. And she reiterates with a cutesy slant: “I cannot do the smurf/I cannot fall in love/I’ll never fall in love.” On the pop-punk “Glendora,” she teases, “You know I always like to play the victim/Would you f--k me? Because I’d f--k me,” in between bemoaning an abusive relationship. The double standards of being a woman are always lingering in the background of Lewis’ lyrics. It’s also impossible to ignore how the song foreshadows the doomed relationship of More Adventurous’ cinematic tragedy “Does He Love You?” Even with her rose-colored glasses, Lewis is nothing if not honest.

On Rilo Kiley, Lewis doesn't hold back, showcasing a confessional style of songwriting that has turned her into a spiritual guide for a cohort of millennial women and musicians. When I interviewed her for the LA Times last year, she said, “I’ve always written about everything; nothing has been off the table. So even on the earliest Rilo Kiley EP, I was writing about sex, but in a different way.” Like Liz Phair’s Exile in Guyville and Alanis Morissette’s Jagged Little Pill before her, Lewis presented sex frankly and with agency from the onset of her career — a throughline in her work that’s allowed young women to feel seen, and provided a blueprint for vulnerable songwriting by everyone from indie artists (Waxahatchee and Phoebe Bridgers) to pop stars (Taylor Swift).

Following the release of the band’s self-titled project, Rilo Kiley would sign with Barsuk Records, to release 2001’s Take Offs and Landings. They then jumped ship to Saddle Creek, for their 2002 sophomore LP The Execution of All Things, before heading to Brute/Beaute Records for 2004’s More Adventurous. They made their final album together, the polished major-label debut Under the Blacklight, in 2007, but Lewis and Sennett soon broke up, transforming the group’s dynamics. By then Lewis’ solo career was beginning to kick off, and Sennett’s focus was shifting to his band the Elected. Rilo Kiley’s future remained uncertain. Boesel first hinted at a hiatus in 2010, and Sennett alluded to a band breakup a year later. They would release the postmortem compilation Rkives in 2013, before Lewis acknowledged in 2014 that Rilo Kiley was disbanding.

For everyone who cherished the band’s guidance — through heartaches, through acid trips, through self-acceptance — Rilo Kiley's self-titled debut serves as a reminder of what they accomplished, a bedrock of vulnerability that helped shape future indie-rock acts and established the strength of Lewis’ songwriting. With its release, fans are likely to wonder whether they could reform and resurrect that approach again. Lewis, for her part, is open to it, telling NME in 2019 that “I did a Postal Service reunion tour a couple of years ago, so I’m open to anything these days. My mantra is ‘Yes.’” B+

Related content: