Like Richard Thompson’s “1952 Vincent Black Lightning,” it’s the kind of song that makes lesser guitarists want to tear their hair out in frustration and remains one of the best Elliott Smith songs. While Smith’s reputation as a brilliant lyricist is well documented, it also bears repeating that he was a phenomenal guitarist, and “Tomorrow Tomorrow” features arguably his most arresting, intricate performance. It’s one of Smith’s most unsettling songs and certainly, among his most ambitious, making you wonder what From A Basement On The Hill would have sounded like had Smith been alive to finish it. That turmoil is reflected in the music, which folds in ghostly backing vocals, hypnotic pianos and queasy guitars. Smith’s lyrics take us inside his tortured mind, where he wrestles with his worsening heroin addiction and paranoia about the music industry. “King’s Crossing” sounds like a nervous breakdown. But, oh how heart-wrenchingly beautiful this song is – as light as a balloon on a breeze.

You don’t have to listen too closely to lyrics such as “So I bought mine off the street” and “All I need is a safe place to bleed” to get the sense that Smith isn’t really singing about love, but a very different kind of drug. This long-unreleased song, which finally saw the light of day on the Heaven Adores You soundtrack, isn’t as breezy as the title would have you think. Listen to the best of Elliott Smith on Apple Music and Spotify. Have we missed one of your best Elliott Smith songs? Let us know in the comments below. In fact, we wouldn’t be surprised at all if your selection of the best Elliott Smith songs was different from our own. It’s easy to form a personal relationship with Smith’s songs, and that’s precisely why it’s so hard to rank them. But the beating heart of his work, from the first song he recorded to the last, was his ability to wring musical beauty out of such ugly subject matter as addiction and depression – things Smith, born on August 6, 1969, wrestled with until his tragic death, at the age of 34, on October 21, 2003. By the time he recorded his final, posthumously released album, From A Basement On The Hill, he was in a studio on a major label’s dollar, rendering his songs in Technicolor with keyboards and strings.

Elliott Smith’s solo career began in a basement on a hill, with little more than an acoustic guitar and a four-track recorder.

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