On “Inger,” a young woman aimless after her father’s death finds herself in a music bar watching a folk guitarist choke out a tune. “When he’s kind of like her dad / a balding young Jewish bohemian / And he’s funny but he’s sad,” Lewis sings. It’s a bittersweet recognition. She sees something familiar in the man on stage, and for a moment, the absence of her father feels a little less vast. The song’s bare acoustics strip away everything but Lewis’ cracked voice, amplifying that fragile connection in his world-worn delivery and the spaces between each line. More than a story about the healing power of music, “Inger” captures The EVEN MORE Freewheelin’ Jeffrey Lewis’s theme of legacy. Notably, the singer he describes looks a lot like Lewis himself. Taken with the album’s homage to Bob Dylan’s most famous record in the midst of the current Dylan renaissance, it’s clear Lewis is reflecting on his career. Capturing the way relationships shift and identities evolve, Lewis pays tribute to the past, reasserting his value at a particularly opportune time.
The album carries the burden of its imperfections. There’s a weight to its looseness, a warmth that feels worn in, like an old coat pulled from the back of a closet. Recorded in just four days in Nashville, the record drifts between past and present, its rough edges intact. Lewis has always worked fast—his early anti-folk records were built on stream-of-consciousness lyrics, bedroom recordings, and vocals that barely held together. Now, violins weave through the songs with a soft twang, at times, stretching out like a whistle in an old Western film—less a call to adventure, more a quiet reminder of time slipping by. Like Dylan, Lewis’s once charmingly rough voice has grown tattered and soft but still carries its former shape. Comparing his deterioration to the gracefully aging great, Lewis jokingly ruminates on being past his prime.
The similarly reflective, standout track “Tylenol PM” captures the restless haze of post-breakup insomnia, where exhaustion and overthinking blur together. Lewis stumbles through late-night desperation, searching for sleep that never comes: “so may dark slumbers grab and hold me / far from what my partner told me / far from memories and thought / just close to this small jar I bought.” These lyrics sit somewhere between a plea and resignation—wanting nothing more than to shut out memory, to let his loss dissolve into sleep. But there’s an irony to this: even as he tries to pull away, the act of singing these words preserves what he wants to forget.
The song moves like a half-remembered dream. Listen closely, and odd sounds creep in—faint ocean waves that could just as easily be a car slicing through the rain, gentle chimes coming from a baby mobile, or a set of keys. The edges blur, one life bleeding into another. The ocean and mobile whisper of childhood, of a time when sleep came easy. The car and keys belong to something else: movement, responsibility, the exhaustion of adult life. With these shifting textures, the song sits in the space between them, showing how time loops back on itself.
Where “Tylenol PM” has a soft approach to life’s challenges, “Sometimes Life Hits You” is more direct. It doesn’t just shrug at life’s hardships, it barrels straight into them. Pain, like aging, is unavoidable. Lewis doesn’t offer an antidote to that inevitability, instead, he lays it out with full honesty. The song treats suffering less like a tragedy and more like a dentist appointment—unwelcome but expected, part of a cycle that no one escapes.
The music mirrors this unshakable truth, rolling forward with a loose, shambling energy. The piano jumps erratically, full of unpolished early rock ‘n’ roll enthusiasm while electric guitar blares. Compared to the rest of the album, where lyrics feel deliberately crafted and melodies are laced with melancholy, this track is raw, almost careless. The shouted hook—“Ow, fuck, that hurts!”—lands like a joke that’s only funny because it’s true. The chorus of voices yelling along brings a sense of camaraderie to the messiness, as if everyone in the room knows exactly what Lewis is talking about. More than any other song on the record, this one embodies the album’s title and theme of aging. It’s reckless and absurd, but so is growing older. There’s no real way to do it gracefully, no way to avoid the bruises. Acceptance runs through the entire album. The EVEN MORE Freewheelin’ Jeffrey Lewis doesn’t try to outrun time or soften its impact. Instead, it lets the weight of years settle in, every frayed vocal and bare arrangement reflecting the quiet wear of experience. The rough production, loose strumming, cracked voices, and moments that feel barely held together become part of the story. Lewis doesn’t offer resolution, only recognition. The EVEN MORE Freewheelin’ Jeffrey Lewis captures the way time accumulates—the past seeping into the present, loss never fully fading, where even the messiest moments carry something worth holding onto.
