How Bad Do You Really Want It? How Hard Will It Make You Cry?

Getting older with Jenny Lewis

It can be difficult for people to understand — that although I love rom coms and loving rom coms is a big part of my whole deal — that I am not necessarily a romantic person. (That is, in and of itself, a whole essay for another time.) I’ve seen and read about too much shit in my lifetime to subscribe to some sort of ooey-gooey idea of love. I prefer a more pragmatic, sober approach to relationships. What is a “happy ending” when no one really knows what the next day will bring? What does it really mean to “end up” with someone when any relationship, at any given time, could run out of fumes or spontaneously combust? You never really know how well-built a foundation is until it collapses. Maybe there was mold and asbestos there the entire time. I believe in love, and long-lasting relationships, but much more important to me than bold and romantic gestures is the hard work you each to do grow and mature as your partner does.

In a world of deep uncertainty, where the Earth is literally wobbling on its axis, you would think that people would be more open to a life of gray areas, to creating something new from the chasms the world has cracked open. And yet I feel like (at least in so far as I can tell), this lack of steadiness has urged some to check off artificial boxes, if only for the illusion of comfort, without understanding that life isn’t as simple as dusting your hands off and saying “Well, that’s taken care of, it’s smooth sailing from here on out.” All of it — no matter what path you end up on or what you choose — has pain and setbacks and joy and mess. And there’s no artist for me who speaks to the breadth and multitude and uncertainty of life like Jenny Lewis.

Jenny Lewis’s music entered my orbit in an extremely conventional and maybe slightly embarrassing way: Via the Grey’s Anatomy soundtrack. In the pilot episode, we hear Jenny singing a Rilo Kiley track, “There’s blood in my mouth ‘cause I’ve been biting my tongue all week/I keep on talking trash, but I never say anything.” The song was called “Portions for Foxes” and later on, the part of the song I really liked was when she said, “And the talking leads to touching, and the touching leads to sex, and then there is no mystery left.” When I got to college and listened to these lyrics again, my ability to relate to them (thanks to my newly gained sexual activity) made me feel more adult than anything had to that point. It is like that, huh?

That being said, I’d known who Jenny Lewis was long before that, thanks to her work as a child actor. It was impossible not to love her in Troop Beverly Hills, one of the many female-centric movies on standby in my household, or even in Big Girls Don’t Cry…They Get Even. For me and so many others, Jenny Lewis was the ultimate Cool Girl, and basically everything she’s said and done since then has helped to maintain this platinum status. One of my favorite Jenny Lewis anecdotes is when she was forming Rilo Kiley with her then-boyfriend Blake Sennett, Sennett asked her if she would sing backup vocals. Jenny said she wouldn’t join the band if she couldn’t sing lead. Now, this, ladies and gentlemen, Is What I Am Talking About. That, as they say, is the stuff.

Now, listen, I liked Rilo Kiley a lot. Big fan. And of the Rabbit Fur Coat album with the Watson Twins, too. But for me things really got cooking when Jenny released The Voyager in 2014. For my money, there is no one who better handles the complexity of aging as a woman and your life maybe not looking how others think it should than Jenny Lewis. The ultimate example of this is, of course, “Just One of The Guys.” For all these years, Jenny has done the impossible. She’s survived as a woman in the male-dominated world of the rock and roll. Survived the sexism, the gross profiles by the Chuck Klostermans of the world, and what I have to imagine what can be a pretty lonely existence. Here, she finally breaks down and admits that despite all of her efforts, she isn’t just one of the guys — not when her male friends lurch towards that inevitable cliche of their much younger girlfriends, and not when she can still be identified as “just another lady without a baby.” Because no matter what, there’s still this nagging feeling that all our work amounts to nothing if we don’t have the husband or kids to complete the picture. There’s more of this on “She’s Not Me” — about the pain of watching a former partner move on with someone more palatable than you.

Two years later, Jenny’s long-term relationship with Johnathan Rice came to an end, and her 2019 album On the Line reflects the dissolution of their partnership. It’s also an album about grief and reckoning with the loss of her parents, both of whom she was estranged from and later reconciled with. As someone who has already lost a parent, who feels the constant threat of the world taking from me more people I love, I’m acutely aware that getting older means only means that threat will be exacerbated. On “Wasted Youth” when Jenny sings “We are here/Then we’re gone/Do something/While your heart is pumping,” you can feel the urgency that only someone who has experienced loss can understand. Jenny’s lyricism always astounds me, but so does her ability to create a lush soundscape within every song. Of course, this is about the kind of access to resources a long career can afford you, like Beck as a producer and Ringo Starr on drums, but also her commitment to her craft. There’s no album for an album’s sake.

With the release of Joy’All, Jenny’s talked about the necessity of seeking out joy after experiencing such a heavy few years, the grief and loss and COVID of it all. Michelle Zauner from Japanese Breakfast spoke about the same thing when she released Jubilee. When you’ve gone through the unspeakable (and in Jenny’s case, more than once), you have to actively seek out that joy. It doesn’t just come to you. And most importantly, the idea that no matter what happens, you have to keep living. There is a lustiness, a zeal for life that her other two do not. It makes for a perfect summer album to listen to on a hot day. And don’t worry — she’s not done illuminating the injustice inherent to the female experience. “I’m not a psycho,” she says, in one of her funnier (and also relatable moments) “I’m just trying to get laid.”

More than anything, Jenny’s singledom for me feels like a testament to the idea that there’s something powerful about choosing to be alone. Her life is hers to live as she sees fit. Yeah, sure, there are complications and hiccups, but just as there would be if she weren’t single. One thing that’s famously not easy? Being married and having children. We talk constantly about the downsides of being single, but not about any of the benefits.

For decades now, Jenny has been associated with coolness. It is my hope that maybe she’ll help do the same thing for living and loving your life, even if it’s out of step with what everyone else’s looks like.