A songwriter with the ability to mine his autobiographical persona, fears and self-loathing to emotional yet comedic effect, Jeffrey Lewis has a catalogue of songs with a unique quality. Dating back to 2001’s ‘The Chelsea Hotel Oral Sex Song’ and 2006’s ‘Williamsburg Will Oldham Horror’, he could weave his heroes and influences into songs riddled with humour. There has always been a defiantly political element to his outlook, most explicitly pursued on 2007’s ’12 Crass Songs’ on which he reimagined songs from the anarcho-punk collective’s history. It has also been apparent on his own compositions such as his guide to action ‘WWPRD (What Would Pussy Riot Do?)’ and his response to anti-vaxxers with ‘I Wanna Be Vaccinated’, an adapted cover of The Ramones’s ‘I Wanna Be Sedated.’

However, in his early years there was often a sharp contrast between his best moments and the overall quality of his albums. Such an accusation could not be levelled at his latest album, ‘The EVEN MORE Freewheelin’ Jeffrey Lewis’ which contains ten top notch compositions that highlight all his best traits. The album’s title and cover borrow from ‘The Freewheelin’ Bob Dylan’ LP, although in Lewis’s case with no pants on to be even more freewheeling. It is a sign that despite the neuroticism and diffidence that he might portray in his songs, he is confident enough in his lyric writing ability to tempt Dylan comparisons.

In addition to his songwriting, Lewis is a magnificent comic artist who sometimes exhibits his artwork during live performances. It gives the idea that his life is a blur of creative endeavour. However, the opening track ‘Do What Comes Natural’ allies itself with the notion that art is far more perspiration than inspiration. For Lewis, doing what comes naturally would entail being a blackhole and staying in bed rather than devoting the time to creating what his critical brain thinks is second-rate art. But as he concludes, “If you act like an artist / It makes you an artist / If you act like a sleazeball / It makes you a sleaze.” It is delivered in his distinctive semi-spoken, nasal New Yorker voice to accompaniment from fingerpicking guitar and Mallory Feuer’s Casio Sk-1 drone.

‘Movie Date’ serves as potted film history but also charts the changing nature of a relationship. From the early days of never getting to the film’s completion through being overwhelmed with passion to now only ever being able to discuss the movie’s beginning as his partner’s falls deep into slumber. The song, though, radiates contentment and good humour.

Resulting from a suggestion by the late David Berman of Silver Jews, who ranked with Lewis as one of the great modern lyricists, about creating a crime romance based on a semi-fantasised relationship with the writer Amy-Rose Spiegel, ‘DCB & ARS’ gallops alongside Feuer’s violin and bassist Mem Pahl’s harmonies. It fits the Lewis template of songs that reference his heroes or admired contemporaries. Going full electric, ‘Sometimes Life Hits You’ begins with a howl of feedback and rollicks along with a repetitive guitar and keys groove. With its observation that whatever insurance you might take out against fire and theft, illness, relationship break up and death, eventually “Life hits you like a chisel to the chest” and repeated chorus of ‘ow, fuck, that hurts”, it is the album’s most infectious and exhilarating tune.

In a rapid shift of mood, ‘Tylenol PM’ is a bleak “laugh or you will cry” piece. To an aching violin Lewis, who has always shown a welcome willingness to critique capitalism complains, “I hate endorsing brands like them / But see / depression and debasement / has got me / doing product placement.” He also dips into the well of self-mocking Jewish humour with the lines, “God… made some Jews hot / made some Jews smart / gave some Jews Jerusalem / but just gave me Tylenol PM” before the song fades out on some backward masking.

Continuing a theme that dates back to ‘Back When I Was Four’, ‘Just Fun’ sets out the trials of attempting an artist’s life. Recorded lo-fi, semi-acoustic with the click of a tape recorder at the song’s beginning and end, it is blisteringly quick-witted in its wordplay (“first see your glowing promise as an actor or a painter / then be honest you’re a hack who knows their glow is getting fainter.”)

Blasting on in an acid-folk, garage rock style, ‘Relaxation’ does not live up to its title, its litany of words and concepts including annihilation, disintegration, oblivion and suicide. Taking a break from first person narration, ‘Inger’ is a muted miniature life story of a young woman growing up in Sweden, losing her father to cancer, coming to America and finding folk clubs and bohemia.

Recorded live with ripples of laughter before it starts, ‘100 Good Things’ could be his gratitude list. To violin accompaniment, his lengthy list includes art, books, ice cream, kissing, his own creative status (“I’m a small but thriving cultural fixture”), his rent being cheap and records (“this entire song could just have been about records.”) In these moments, it could be the ultimate feel-good song but it returns to its opening twist (“my perspective needs a radical twist / I know there’s reasons I should exist / My life is good, I just have to insist.”) It is a masterpiece of emotional storytelling.

‘The EVEN MORE Freewheelin’ Jeffrey Lewis’ ends with the ridiculously mournful ‘The Endless Unknown’, its slow tempo guided by violin and Lewis’s phrasing sounding like late 80s Lou Reed, cursing his “stupid, stupid brain, and all its dumb smart thoughts.” It completes a journey with an artist who outwardly sounds unsure of himself yet whose pokes and prods at the doubts assailing him make for an entertaining and enlightening account that reflects the neuroses of the human condition.

Jeffrey Lewis: The EVEN MORE Freewheelin’ Jeffrey Lewis – Out 21 March 2025 (Blang Records)

Jeffrey Lewis – “Sometimes Life Hits You” | Music Video

I was editor of the long-running fanzine, Plane Truth, and have subsequently written for a number of publications. While the zine was known for championing the most angular independent sounds, performing in recent years with a community samba percussion band helped to broaden my tastes so that in 2021 I am far more likely to be celebrating an eclectic mix of sounds and enthusing about Made Kuti, Anthony Joseph, Little Simz and the Soul Jazz Cuban compilations as well as Pom Poko and Richard Dawson.