Spinning in the rock room today is Elliott Smith’s 2003 single “Pretty (Ugly Before).” The song would be Elliott Smith’s last official record made during his lifetime.  It would later be released on the posthumously curated 2004 LP From a Basement on the Hill following Smith’s death.

“Pretty (Ugly Before),” was delivered as a non-album single and Smith’s first following 2000’s critically acclaimed LP Figure 8. While touring the record Smith and his road band stopped into Fort Apache Studios in Cambridge, MA to record a studio version of the song.

Because of a multitude of reasons including personal struggles the song wasn’t released until August of 2023 when Smith was working on his next full-length album which would never become realized. Released on Suicide Squeeze records as a single b/w “A Distorted Reality Is Now a Necessity to Be Free.” the track would land at # 85 on the single charts.

The song had been road tested over the course of the tour and was broken in like a beloved pair of jeans worn at the knees. It is one of Smith’s most lovingly fashioned melodies and emphasizes the aching hallmarks of his songwriting acumen.

The song’s hazy arrangement features delectably pressed double tracked vocals and pastorally punky guitars. Smith’s arrangement is layered with every single instrument providing an essential detail to the overall spread. The song reads like novel and sounds like a symphony through lovingly basic changes and earnest lyricism.

The track begins on a transient Mellotron drone that was recreated by a Casio SK-1 sampler and elicits the ethereal reveal of a daybreak.

Smith’s pinched singing enters on a detailed strumming drift. His vocal is weary and punctuated with a blurry resignation but exquisitely rendered. Despite his faded timbre there is the glow of hope, a underlying theme of redemption.

The song broken down into its essential elements is two stanzas of poetic contrasts, day, night, pretty, ugly, high, low, and expressed in Smith’s indelible way of pulling the feelings from the deepest recess of his soul and inviting the listener to relate. He had the innate ability to say so much with so little extraneous verbiage. His admission of ugliness becoming beauty is commendable and illustrates an artistic honesty rarely ventured into by pop musicians.

When the drums enter the song fissures into a haunted Americana-tinged anthem replete with crisp and argent guitars. Smith lends a quirky honky tonk lick between verses while Aaron Embry’s piano delicately quotes a fractured melody line that immediately stirs the wellspring of emotional content into an overwhelming melodic maelstrom.

It’s not known if Smith planned to include this song on his next album because it wasn’t included in a prospective track listing, he later provided to producer Fritz Michaud. What can be confirmed is that the song was important to Smith, as in the interim between its 2000 recording session and its 2003 single release, it was a mainstay in his performances and never far from his mind.

The middle eight of the song soars through its changes with Smith’s guitar playing a stunningly dramatic hybrid of the Byrds and Big Star. When he lands back on the C chord with a heavy strum the song turns lotus flower, a phoenix rising in both optimism and dread.

The song returns to the opening verses, now sung with thoughtful accompaniment from Smith’s former bandmate Sam Coomes (Heatmeister) who provides sympathetic and perfectly echoed accompaniment. An emotive climax is created through the overlapping voices and chiming guitars.

The song then retreats into the blue hour through a wash of backwards guitars and then to silence. When you listen to the tune it’s like you’ve been through something when it ends. “Pretty (Ugly Before)” is one of those songs that changes your head and once you have listened it’s hard to understand who or what you were before heard it.

It’s somehow foreboding, yet beautifully optimistic in its soulful core. Its delicacy belied by its power, its hopefulness increased by its inherent sadness. Perhaps the songs majesty is because it’s the last one he willingly shared in his life and that provides it with an elegant finality.

Here is a minimalist live version (from 2000?) that was included in Autumn de Wilde’s 2007 book Elliott Smith that features Jon Brion on harmonium and is worthy of deep inspection.