“I thought my head would be chopped off immediately when it came out, because at the time it was so opposite to the grunge thing that was popular” – 5 essential Elliott Smith songs to start with

Elliot Smith performs on stage at Glastonbury Festival, United Kingdom, 2000
(Image credit: Martyn Goodacre/Getty Images)

When it comes to charting the epicentres of great indie music over the last decades, Portland Oregon comes well up on the list. The ‘Rose City’ has yielded a whole host of inspirational names, from Decemberists, Modest Mouse and Blind Pilot to The Shins, Sleater Kinney and Esperanza Spalding. 

Then, of course, there is Elliott Smith, a uniquely gifted singer-songwriter with a distinctly melancholic sound. Across five hugely influential studio albums and one posthumously compiled studio album, Smith melded folky Beatles-style melodicism with lyrics that defied convention. His sound was unassuming yet his songs exuded songwriting craftsmanship. 

Smith had a fragile and distinctive vocal style, a "whispery, spiderweb-thin delivery" as AllMusic’s Steve Huey described it. Beneath it all was a deep vulnerability. He was diagnosed with depression and attention deficit hyperactivity disorder (ADHD) and his struggles with mental illness and addiction informed his work. 

He was born in 1969 in Omaha, Nebraska and raised in Texas. He had a difficult childhood and at the age of fourteen Smith left his mother’s home and moved in with his psychiatrist father in Portland, Oregon . 

He studied philosophy and political science at a college in Massachusetts and after graduating in 1994 he returned to Portland and formed Heatmiser, a band whose upbeat pop-rock melodies belied a deep, dark underbelly. By 1996 they were signed to Virgin Records for their third album but Smith’s solo career was already far eclipsing that of his band.

In the early '90s, Smith’s girlfriend had convinced him to send a collection of home-recorded four-track songs to Cavity Search Records. The label released them in their entirety as his debut album Roman Candle (1994). 

“I thought my head would be chopped off immediately when it came out,” he told Under The Radar in 2003, “because at the time it was so opposite to the grunge thing that was popular ... The thing is that album was really well received, which was a total shock.”

His self-titled second album followed in 1995, on indie label Kill All Rock Stars. It’s arguably his bleakest album, with tracks such as Needle In The Hay and The White Lady Loves You More alluding to drug usage. 

In 1997, Smith moved to New York. By then, he was drinking heavily, but in creative terms, it was a landmark year. In February, he released Either/Or, an album that featured a fuller, richer sound. It remains his masterpiece. Smith had always been influenced by the pop mastery of The Beatles – particularly the ‘White Album’ – and their presence can be felt on the full-band tracks.

Yet it’s the sparser, more subdued numbers such as Angeles and Between The Bars that really resonate, with their acoustic fingerpicking and hushed, atmospheric late-night introspection.

Either/Or was also the album that launched Elliott Smith into the major league, after film director Gus Van Sant asked him to contribute songs for the soundtrack of his new film Good Will Hunting. Angeles and Say Yes were selected and Smith recorded an orchestral version of Between The Bars with composer Danny Elfman. He also contributed a new track Miss Misery and the song No Name #3  from the Roman Candle album. 

Smith was nominated for an Academy Award for Miss Misery and on 23 March 1998, wearing a white suit, he played an abridged version of the song at the Academy Awards ceremony, accompanied by the house orchestra. "The Oscars was a very strange show,” he told The Boston Globe. “...I wouldn't want to live in that world, but it was fun to walk around on the moon for a day." 

Smith landed a major deal with DreamWorks Records but he sunk into depression and threatened suicide on numerous occasions. He rallied for the follow-up album XO in 1998, a more elaborate affair with Beatles-esque production, which reached No. 108 in the Billboard charts. In 1999, he contributed a cover of The Beatles’ Because for the film American Beauty and in 2002 he recorded his fifth solo album Figure 8 at Abbey Road Studios. The album was praised for its complexity and power pop style. 

An extensive tour followed and for the next two years, Smith laboured over his sixth solo album, but he would not live to see its completion, On 21 October 2003, he was found dead at his home with  two stab wounds in his chest. The coroner was unable to determine whether he had killed himself or been murdered. 

One year later, Smith’s estate commissioned the completion of the album he had been working on, From A Basement On The Hill, a 15-track single album that was warmly received and reached No. 19 in the Billboard charts. 

Twenty years on, Elliot Smith’s quiet and elegant-crafted songs sound as fresh and vital as ever. Here was a songwriter whose intense fragility gave him a unique perspective. Across the course of his troubled and tragically short life, he left behind a back catalogue that is as insightful as it is utterly captivating. 

1. Angeles  – Either/Or (1997)

A high keyboard note intros this track, which then segues into gentle, intricate fingerpicking over the Am-D-Em-D-C chord sequence on the first line of the verse. The song focuses on the hedonism and brutality of Los Angeles and his struggle to find a sense of belonging in the city where he would meet his end. 

Smith’s vocals have rarely sounded so intense and imploring. His voice was frequently double-tracked in the studio, which adds weight yet also boosts the fragility and emotion of his delivery.

“I could make you satisfied in everything you do / All your secret wishes could right now be coming true / And be forever with my poison arms around you.” 

Smith’s primary acoustic was a Yamaha FG 180 Red Label, with a Bill Lawrence magnetic pickup, and this is the guitar that features on this track and can be seen in most of his YouTube clips. He also played a Martin D-18.  

Angeles is one of the songs chosen by director Gus Van Zandt for the soundtrack of his film Good Will Hunting. It’s a beautiful, poignant track and remains one of his most beloved and enduring works.

 Between The Bars  – Either/Or (1997)

One of Smith’s most popular and memorable tracks and another of the songs used by Gus Van Zandt on the soundtrack to the film Good Will Hunting. Running at just 2:20, it’s an absolute gem of a track and features some of his most intimate and tender lyrics.

The song is actually in waltz time, although you barely notice, distracted as you are by his emotive delivery and the narrative about getting drunk with a lover and promising to keep sadness at bay. 

“The promises you'll only make / Drink up with me now / And forget all about the pressure of days / Do what I say and I'll make you okay / And drive them away / The images stuck in your head.”

Sparse acoustic guitar is the sole instrumentation, which only heightens the song’s intensity. The fact that the title could allude to either incarceration or inebriation adds to the intrigue.

3. Bled White  – XO  (1998)

XO was the album that marked Elliot Smith’s shift from introspective acoustic indie to a more full-blown pop sound. It was also the first one fuelled by the commercial clout of a major label, DreamWorks Records, although as a retrospective review in BBC Music put it: “The budget might have gone up, but Smith's masterful way with an understated melody and melancholic lyric remained firmly intact".

It’s a lush full full-bodied sound with ethereal dream-like flourishes, offset by fragile, introspective vocals. 

This track intros with a nicely off-kilter acoustic guitar riff for eight bars, before the whole band kicks in. As ever with Smith, the chords and top line melody always veer towards the unexpected. 

This is a bigger, bolder sound with a carefree vibe offset by lyrics about loss and self-doubt. It remains one of his most beloved and enduring works.

“And the doctor’s orders / Drinking to distraction’s such a waste of time / Drinks all night to take away this curse / But it makes me feel much worse / Bled white”. 

 4. Miss Misery  (1997)

This is the song that briefly made Elliott Smith a household name after it featured in the closing credits of the Oscar-winning film Good Will Hunting and was nominated for ‘Best music, original song’. Smith performed it at the 70th Academy Awards ceremony on 23 March 1998, while wearing a Mark Twain-style white suit. He initially refused the invitation to perform the song and only changed his mind when the Academy allegedly told him they would ask someone else to perform the song instead. 

I walked out and Jack Nicholson was sitting about six feet away, so I avoided that area and I looked up at the balcony in the back and sang the song

Smith later described the experience as "ridiculous” but adding that “at a certain point I threw myself into it because it seemed to make my friends happy... I walked out and Jack Nicholson was sitting about six feet away, so I avoided that area and I looked up at the balcony in the back and sang the song”.

It’s a wistful, haunting track, with a gentle fingerpicking intro, over which Smith sings in quiet, breathy tones: “I'll fake it through the day / With some help from Johnnie Walker red / Send the poison rain down the drain /To put bad thoughts in my head”.


At 0:20 on the 1997 single version, drums, bass and keyboards kick in, underpinning the descending top line melody with a lilting groove. A previous version of the track was recorded in early 1997 and appears on the 2007 posthumous collection New Moon. It’s a gorgeous version, and held up by many as one of his finest.

5. Waltz #2  – XO  (1998)

Another waltz time track yet one with a lyrical ferocity not usually associated with that jaunty toe-tapping time signature. It’s a heartbreaking song about his mother and his stepfather, the latter with whom Smith had a deeply troubled relationship, prompting him aged fourteen to leave Texas to live with his father in Portland, Oregon. 

There’s a chirpy, country feel to the intro, with its simple boom-chick-chick kick and snare. Here, Smith plays a 1968 Gibson ES-330, the instrument he had used since his days in the band Heatmiser.

Like many great songs, it’s the contrast between upbeat instrumentation and dark lyrical intent that is so compelling. Smith’s vocal phrasing, like all aspects of his music, is never predictable, yet inventive and assured. 

“She appears composed so she is I suppose,” he begins on the second verse, “Who can really tell / She shows no emotion at all / Stares into space like a dead china doll”. 

It’s a stunningly realised composition – raw, heartfelt and true, right down to the last fading cello at its close. 

Neil Crossley

Neil Crossley is a freelance writer and editor whose work has appeared in publications such as The Guardian, The Times, The Independent and the FT. Neil is also a singer-songwriter, fronts the band Furlined and was a member of International Blue, a ‘pop croon collaboration’ produced by Tony Visconti.