When the Rilo Kiley singer and guitarist Blake Sennett wrote them 25 years ago, he concurred with the lyrics of “Pictures of Success,” a song about longing to arrive at a destination despite, or because of, the inability to fully imagine it.
“I’m ready to go / Ready to go / Ready to go,” he howls on the track’s refrain, harmonizing with the song’s co-writer and the band’s lead singer, Jenny Lewis, over a bed of chiming guitars.
But the words hit him differently now.
“I’m not as ready to go as I was then,” joked Sennet, 51, on a recent video call from Los Angeles with his bandmates: Lewis, 49; the drummer Jason Boesel, 47; and the bassist Pierre “Duke” de Reeder, 52.
“You already went,” Boesel quipped.
“We should license that song to, like, Cialis, or something,” Lewis suggested. “Ready to go!”
Life comes at you fast. Since the release of the first Rilo Kiley EP in 1999, the band has survived affiliation with Hollywood, straddled mid-aughts indie exuberance with its third album, “More Adventurous” (2004), graduated to mainstream popularity with a follow-up, “Under the Blacklight” (2007), split up under tense circumstances and — after the marriages, children and self-reflection of early middle-age — found its way back together again.
On May 5, Rilo Kiley will play its first official show since 2008 — the start of a 24-date reunion tour. A greatest hits album, “That’s How We Choose to Remember It,” will be released on the 9th.
“It’s a tender and scary and magical thing,” Lewis said. “But who wouldn’t want to go back to being in their mid-20s again?”
The journey here began a little more than five years ago, in January 2020, when Sennett, who moved to Nashville in 2015, was visiting de Reeder in Los Angeles. The bassist invited Lewis and Boesel to join them for a casual barbecue, and the four found themselves in a room together for the first time in more than a decade.
When the tour supporting “Under the Blacklight” ended, in the spring of 2008, Rilo Kiley was effectively over. The album was the most commercially successful of the band’s career, hitting No. 22 on Billboard’s Top 200, with more than 186,000 units sold, and spawning a hit single, “Silver Lining,” that has been streamed more than 37 million times on Spotify.
But recording had been a struggle. The relationship between Sennett and Lewis, who met as teenagers and were romantically involved during the first incarnation of the band, had grown increasingly prickly. (Both released side projects — Sennett’s “Sun, Sun, Sun” with the Elected, and Lewis’s “Rabbit Fur Coat” with the Watson Twins — on the same day in 2006.) On tour, their long-simmering tension had finally boiled over.
“I think the end was nigh the moment we first hooked up,” Lewis said. “We never really fixed the issues that we had as a couple. I remember a fight that we had, after we had first broken up, where I threw Blake’s Pink Floyd CD out of the window. And then we were hanging out with other people, which got very messy on the road.”
Looking back, everyone agrees that it’s remarkable the band lasted for as long as it did.
“We didn’t have the tools back then to sit down cross-legged and pass the ball back and forth and share our feelings, or whatever,” Sennett said. “We just kind of stuffed it all down and became passive aggressive. Eventually, things devolved.”
At the 2020 barbecue, their differences were far enough in the past that, for the first time, reconciliation felt possible. Soon after, Lewis relocated to Nashville during the pandemic, and Sennett came over and helped her work on her car. On another visit, he introduced her to his young daughter.
“We connected when the world was shut down, and that meant a lot to me,” Lewis said. “It put things into focus.”
In 2023, the organizers of the nostalgia-tinged music festival Just Like Heaven reached out to Lewis’s manager to ask if Rilo Kiley would consider performing. At the time, she was on a tour with the indie electro-pop act the Postal Service, commemorating the 20th anniversary of its millennial-beloved album, “Give Up.” Seeing the emotional outpouring from crowds who’d grown up with the music as the soundtrack of their lives made Lewis imagine creating a similar experience for Rilo Kiley fans.
“I’m looking at people in the audience while I’m playing, and the connection was just so beautiful and powerful,” she said. “It really inspired me to want to do that with our songs.”
A COUPLE OF WEEKS AGO, at de Reeder’s recording studio in Los Angeles’s Highland Park, the band assembled to start rehearsals for the reunion tour. They unearthed their old instruments and gear, including a Roland keyboard used to record “The Execution of All Things,” their breakthrough sophomore album from 2002.
Lewis and Sennett started the band in 1998, when they were 22 and 24. Both were former child actors who found in music what they had yearned for while shuttling between film and television jobs: autonomy, immediacy, a community that felt real.
At Lewis’s apartment in West Hollywood, which she shared with three roommates, they wrote dozens of songs inspired by heartache, sex, family lore and pop culture.
“It just unlocked something in me,” she said. “I have all these shoe boxes from that era filled with notebooks of songs and insane lyrics. I couldn’t stop.”
Taking cues from their forerunners in left-of-center, confessional rock music, including Modest Mouse, Built to Spill and Elliott Smith, Rilo Kiley charted the soaring highs and hairpin turns of youthful identity formation.
Katie Crutchfield, of the alt-country band Waxahatchee, said discovering the band in high school was what pushed her to make her own music.
“There’s a powerful femininity to the way Jenny writes and presents herself that made me feel like I could do that,” said Crutchfield, who tattooed the cover of “The Execution of All Things” on her arm. “As a 15-year-old girl in Alabama, I just hadn’t had examples of a person like her. It rocked my entire world.”
Mike Mogis, of the indie-folk band Bright Eyes, who produced “The Execution of All Things” and “More Adventurous,” said the band epitomized the alternately disillusioned and idealistic spirit of the age.
“The characters in Jenny’s songs always have a troubled past or present, but at the same time there’s some hopefulness to it,” Mogis said. “It was the best of all worlds.”
Apart from the band’s interpersonal conflicts, there were some growing pains. In 2004, Rilo Kiley began working with Warner Bros. Records, parting ways with the indie label Saddle Creek and a collective of D.I.Y.-minded musicians in Omaha led by the Bright Eyes founder Conor Oberst.
Signing to a major helped Rilo Kiley reach a wider audience and get its songs on the radio and in movies and television. But Lewis felt anxious about preserving the band’s authenticity, and clashed with Warner over its marketing.
“On our first video with them,” for the “More Adventurous” single “Portions for Foxes,” “I was wearing this cute little vintage Pucci dress and they wanted me in something more revealing,” she recalled. “That was not something I was willing to do. I was like, ‘No, no, no. I pick out my own clothes.’”
Although Lewis and the others said they had a positive experience at Warner overall, the greatest hits album will be released via Saddle Creek.
More than 15 years since their last performance, the band members are preparing themselves mentally, physically and emotionally for a return to the stage. The third stop on the tour is the Just Like Heaven festival — at the Rose Bowl in Pasadena, Calif. — which will be headlined by Vampire Weekend and attended by tens of thousands of fans.
Before hitting the road, they’ve planned an intimate friends and family show in Los Angeles to work out lingering nerves.
“I don’t want to prove anything, but I would like to illustrate,” Boesel said, “that we’re an authentic band and these are authentically wonderful songs that people love.”
Earlier this month, after a week of rehearsals, muscle memory had already begun to kick in.
“I look around and everyone’s in their old spots,” de Reeder said. “It’s like, ‘Oh, yeah. We’re doing this thing.’”
Additional camera operator: Grant Spanier.
