What is Elliott Smith's Saddest Song?

Elliott Smith is a hugely iconic and influential musician, known for his intimate and personal music. An indie rock legend, with album after album filled with raw emotion. Elliott kicked off his solo career in 1994 while still in his band Heatmiser, quickly building a name for himself in his city of Portland, Oregon. His debut, "Roman Candle", was released that year, followed by his self-titled effort the next year in 1995.

Elliott's band Heatmiser dissolved in 1996, which gave him a lot more time to devote to his solo material. 1997's "Either/Or" was a clear evolution of Elliott's sound, incorporating more instrumentation. A noticeable shift away from the barebones nature of his first two albums. 1998's "XO" gave Elliott his big break, being his first on a major label. Largely due to the success of his track "Miss Misery" being used in the film Good Will Hunting. The track was nominated for an Oscar, for which Elliott gave a haunting performance.

2000's "Figure 8" saw Elliott continue in the direction of "XO," featuring a more pop-friendly sound, yet still retaining his best qualities. Elliott's career was blossoming, yet trouble was on the horizon. In the early 2000s, he got hooked on drugs, which led to a massive downward spiral. While in the throes of addiction, he began writing songs for his next album. But before he could finish the album, he passed away on October 21st, 2003, at the age of 34. This album saw a release the next year, titled "From a Basement On the Hill", which contained a familiar sound, while also being very experimental in places.

Elliott Smith has become the poster boy for "sad indie music" for better or for worse. While I don't think most of his music is sad, he certainly had a number of songs that are. In this video, I discuss a song that I find to be Elliott's saddest.

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