Led by former child actors Jenny Lewis (vocals, guitar, keyboards) and Blake Sennett (guitar, vocals), the L.A.-based quartet held its first practice in 1998. Bassist Pierre de Reeder and drummer Dave Brock (later replaced by ex-Foundation Lassie member Jason Boesel) completed the lineup, and a weekly residency at the Spaceland nightclub in Silverlake allowed Rilo Kiley to hone its mix of classic pop, country, torch song, and folk.

The debut album Take Offs and Landings was released in 2001 by the Seattle-based Barsuk Records, also home to Death Cab for Cutie (whose lead singer, Ben Gibbard, would later enlist Lewis' help on the Postal Service's gold-selling debut). Although Lewis' side projects and star appeal would eventually make her the focal point of Rilo Kiley, Take Offs was the work of a dually fronted band, with Sennet contributing lead vocals on four tracks. The band supported the album by hitting the road, during which they were introduced to Omaha native Tim Kasher (Cursive, the Good Life) at San Francisco's Great American Music Hall. Both of Kasher's bands were signed to Omaha's Saddle Creek Records, whose solid roster and promise of creative freedom attracted Rilo Kiley's interest. Although the exclusive label had rarely opened its doors to bands outside of Omaha's city limits, they nevertheless signed Rilo Kiley and released the band's twangy sophomore effort, The Execution of All Things, in October 2002.

After touring with the likes of the Breeders, Pedro the Lion, and Superchunk, the band took some time off to pursue separate projects. Lewis contributed backing vocals to the Postal Service's Give Up, later touring with the band as well, while Sennett and Boesel released their debut album with the Elected. Rilo Kiley reconvened to record 2004's More Adventurous, but creative differences with Saddle Creek convinced the band to create their own label, Brute/Beaute Records (an imprint under the Warner umbrella), for the record's official release. Buoyed by a cohesive sound, several singles, and big-time distribution from Warner Bros., More Adventurous greatly heightened the band's profile. Tours with Coldplay and Bright Eyes followed, and the popular song "Portions for Foxes" was featured on the TV drama Grey's Anatomy.

Following the success of their third album, Rilo Kiley took yet another break to focus on personal projects. Boesel toured the world as Bright Eyes' drummer and worked with Sennet to record the Elected's sophomore release, Sun, Sun, Sun, but all efforts paled in comparison to the critical success of Jenny Lewis' solo debut, Rabbit Fur Coat. Released by Team Love Records (co-founded by Lewis' onetime labelmate, Bright Eyes' Conor Oberst) and featuring vocal duo the Watson Twins, Rabbit Fur Coat charted higher than any Rilo Kiley album to date. Lewis supported the album by touring three times in 2006, earning accolades from such media sources as Rolling Stone, Entertainment Weekly, and NPR. Nevertheless, Warner Bros. had previously signed Rilo Kiley in the wake of More Adventurous' success, and the group reconvened once again to enjoy the major-label backing they'd worked so hard to achieve. Under the Blacklight, the band's first album on a majors' tab (and fourth full-length record overall), was released in August 2007.

Jenny Lewis released a second solo album called Acid Tongue in 2008, a tacit admission that Rilo Kiley was starting to unravel. No confirmation of the band's future was quick to arrive, however. In 2010, Jason Boesel told Paste the band was on hiatus and, then next year, Blake Sennett cryptically said the band was finished, but both members teased out a rarities compilation. That rarities set, called Rkives and featuring finished unreleased songs, finally appeared in the spring of 2013. ~ Andrew Leahey