
‘Williamsburg Will Oldham Horror’: Jeffrey Lewis’ stunning ode to artistic alienation
On a rainy September evening in Leeds nearly three years ago now, I battled the elements on my way to The Lending Room, eager to finally witness one of my favourite artists perform in the flesh. I was probably about 13 when I first heard the distinctive anti-folk ramblings of Jeffrey Lewis, and his album Manhattan became a vital accompaniment to my teenage years – for better or worse. Standing in the front row of the small Leeds venue, every emotion I had felt while listening to that record came crashing home upon witnessing Lewis rattle off a bone-chilling performance of ‘Williamsburg Will Oldham Horror’ in front of my very eyes.
Originally released in 2005 on the album City and Eastern Songs, the track was not one that I was intimately familiar with when I went to see Lewis in Leeds. Nevertheless, his flawless rendition of the song, throwing out awe-inspiringly emotional lyrics with apparent ease and even slipping in a commendable Bob Dylan impression, spurred me on to immerse myself in the six-minute track. After years of listening to the song on a near-daily basis, ‘Williamsburg Will Oldham Horror’ reads as one of the greatest odes to alienation and DIY music-making ever put to tape.
Within the song, Lewis glumly tells the tale of travelling to Williamsburg, New York, via the subway ‘L train’ to remaster an old album. While on the train, the singer spots somebody who appears to be Bonnie Prince Billy himself, Will Oldham – identified by his sunglasses. Over the course of a few verses, all of Lewis’ worries, fears, and self-doubts are expressed with great desperation, all aimed towards the Oldham lookalike. “How long should an artist struggle before it isn’t worth the hassle?” asks Lewis.
Every DIY artist has asked themselves that question at one point or another: is it better to stay principled and poor or sell out your art and strive for mainstream commercial success? Certainly, it is a question that Jeffrey Lewis has been forced to come to terms with throughout his extensive work as one of New York’s most prolific DIY artists.
By 2005, the anti-folk scene that had first thrust him into the spotlight had produced colossal stars like Beck or Regina Spektor, but Lewis was still stuck on that subway train pouring his heart out to someone who may or may not be Will Oldham.

No other song deals with the constant internal struggle of attempting to be an artist quite as adeptly or in such an all-encompassing manner as Lewis on ‘Williamsburg’. During its six-minute narrative, the songwriter destroys and rebuilds every notion of noble artistry, questioning whether it is better to merely give up on art and do something more beneficial to society. It is as though Lewis split open his own head and let listeners have a good old look inside.
At one point, Lewis points out that musical success is all relative, telling Oldham, “If you hear a record by Bob Dylan or Neil Young or whatever. You must start thinkin’: Yeah, people like me, but I won’t be that good ever.” Before musing, “I’m sure the thing is probably Dylan himself, too, stayed up some nights wishing he was as good as Ginsberg or Camus.” It’s unclear what level of the hierarchy Lewis occupies on that scale, but his lyricism on this song, in particular, is as profound and universal as they come.
The narrative of the song resolves itself by the Will Oldham figure brutally assaulting Lewis on the subway tracks before departing with the words “Artists are pussies,” giving the songwriter reassurance that “I’m just a pussy, that’s okay, ‘Cause in a few months maybe, I’ll put out something good.” It is difficult to think of any other songwriter who could pack such a dense, extensive internal battle of artistic alienation into a tight six-minute anti-folk anthem, but that only speaks to Jeffrey Lewis’ unparalleled position as a DIY artist.
Sure, Lewis is largely a DIY artist by necessity; his sprawling discography, while profound, has never been designed with mainstream appeal in mind. Yet, songs like ‘Williamsburg Will Oldham Horror’ exist as a homage to grassroots artists across the world who dedicate themselves to the creation of art that they deem worthwhile, regardless of whether that brings commercial or mainstream success. Admittedly, the song is also an ode to the constant mental struggle that comes with those life choices, but Lewis’ lasting career is living proof that DIY art is worth pursuing.
So, when I stood in front of Lewis’ battered guitar as he belted out the six-minute track at break-neck speed, I could not help but bask in the profound genius of his work. It was undoubtedly the best live performance of a song I have ever witnessed, and it was delivered with such a casual nonchalance which spoke to the understated artistry of the songwriter.
With a brand new album, The Even More Freewheelin’ Jeffrey Lewis, on the horizon, the songwriter continues to provide a voice for everybody who has dedicated themselves to pursuing a noble, artistic cause in spite of their self-doubting instincts.