A successful child actor turned indie-rock sweetheart with Rilo Kiley, a solo artist beloved by the famed and famous, Jenny Lewis would appear to have led a gilded life. But her truth—and there have been intimations both in song lyrics and occasionally in interviews—is of a far darker inheritance. “I come from working-class showbiz people who ended up in jail, on drugs, both, or worse,” Lewis tells Apple Music. “I grew up in a pretty crazy, unhealthy environment, but I somehow managed to survive.” The death of her mother in 2017 (with whom she had reconnected after a 20-year estrangement) and the end of her 12-year relationship with fellow singer-songwriter Johnathan Rice set the stage for Lewis’ fourth solo album, where she finally reconciles her public and private self. A bountiful pop record about sex, drugs, death, and regret, with references to everyone from Elliott Smith to Meryl Streep, On the Line is the Lewis aesthetic writ large: an autobiographical picaresque burnished by her dark sense of humor. Here, Lewis takes us through the album track by track. “Heads Gonna Roll” “I’m a big boxing fan, and I basically wanted to write a boxing ballad. There’s a line about ‘the nuns of Harlem'—that’s for real. I met a priest backstage at a Dead & Company show in a cloud of pot smoke. He was a fan of my music, and we struck up a conversation and a correspondence. I’d just moved to New York at the time and was looking to do some service work. And so this priest hooked me up with the nuns in Harlem. I would go up there and get really stoned and hang out with theses nuns, who were the purest, most lovely people, and help them put together meal packages. The nuns of Harlem really helped me out.” “Wasted Youth” “For me, the thing that really brings this song, and the whole record, together is the people playing on it. [Drummer] Jim Keltner especially. He’s played on so many incredible records, he’s the heartbeat of rock and roll and you don’t even realize it. Jim and Don Was were there for so much of this record, and they were the ones that brought Ringo Starr into the sessions—playing with him was just surreal. Benmont Tench is someone I’d worked with before—he’s just so good at referencing things from the past but playing something that sounds modern and new at the same time. He created these sounds that were so melodic and weird, using the Hammond organ and a bunch of pedals. We call that ‘the fog’—Benmont adds the fog.” “Red Bull & Hennessy” “I was writing this song, almost predicting the breakup with my longtime partner, while he was in the room. I originally wanted to call it ‘Spark,’ ’cause when that spark goes out in a relationship it’s really hard to get it back.” “Hollywood Lawn” “I had this for years and recorded three or four different versions; I did a version with three female vocalists a cappella. Then I went to Jamaica with Savannah and Jimmy Buffett—I actually wrote some songs with Jimmy for the Escape to Margaritaville musical that didn’t get used. We didn’t use that version, but I really arranged the s*** out of it there, and some of the lyrics are about that experience.” “Do Si Do” “Wrote this for a friend who went off his psych meds abruptly, which is so dangerous—you have to taper off. I asked Beck to produce it for a reason: He gets in there and wants to add and change chords. And whatever he suggests is always right, of course. That’s a good thing to remember in life: Beck is always right.” “Dogwood” “This is my favorite song on the record. I wrote it on the piano even though I don’t think I’m a very good piano player. I probably should learn more, but I’m just using the instrument as a way to get the song out. This was a live vocal, too. When I’m playing and singing at the same time, I’m approaching the material more as a songwriter rather than a singer, and that changes the whole dynamic in a good way.” “Party Clown” “I’d have to describe this as a Faustian love song set at South by Southwest. There’s a line in there where I say, ‘Can you be my puzzle piece, baby?/When I cry like Meryl Streep?’ It’s funny, because Meryl actually did a song of mine, ‘Cold One,’ in Ricki and the Flash.” “Little White Dove” “Toward the end of the record, I would write songs at home and then visit my mom in the hospital when she was sick. I started this on bass, had the chord structure down, and wrote it at the pace it took to walk from the hospital elevator to the end of the hall. I was able to sing my mom the chorus before she passed.” “Taffy” “That one started out as a poem I’d written on an airplane, then it turned into a song. It’s a very specific account of a weekend spent in Wisconsin, and there are some deep Wisconsin references in there. I’m not interested in platitudes, either as a writer or especially as a listener. I want to hear details. That’s why I like hip-hop so much. All those details, names that I haven’t heard, words that have meanings that I don’t understand and have to look up later. I’m interested in those kinds of specifics. That’s also what I love about Bob Dylan songs, too—they’re very, very specific. You can paint an incredibly vivid picture or set a scene or really project a feeling that way.” “On the Line” “This is an important song for me. If you read the credits on this record, it says, ‘All songs by Jenny Lewis.’ Being in a band like Rilo Kiley was all about surrendering yourself to the group. And then working with Johnathan for so long, I might have lost a little bit of myself in being a collaborator. It’s nice to know I can create something that’s totally my own. I feel like this got me back to that place.” “Rabbit Hole” “The record was supposed to end with ‘On the Line’—the dial tone that closes the song was supposed to be the last thing you hear. But I needed to write ‘Rabbit Hole,’ almost as a mantra for myself: ‘I’m not gonna go/Down the rabbit hole with you.’ I figured the song would be for my next project, but I played it for Beck and he insisted that we put it on this record. It almost feels like a perfect postscript to this whole period of my life.”