Had he died at 27, he would have been in the club

Many of his best songs relate to death

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If there was ever a likely candidate for membership in the forever 27 club, it was Nick Drake. He was a critic's darling, a pioneer in the wispy alternative folk genre, and was the classic melancholy, moody English singer-songwriter. He wanted so badly to be appreciated and to be successful, but it was not his fate - in his lifetime. He died a few months shy of his 27th birthday at the home of his parents in England, victim of what has been described as an accidental overdose of an antidepressant medication. There are, of course, other theories about the cause of his death.
Drake only recorded and released 3 albums while he was alive - Five Leaves Left, Bryter Layter, and Pink Moon. Other unreleased recordings were made available posthumously, and Drake's influence and reputation have evolved and developed to almost mythic proportions based on this small recorded output. Contrary to what you might think, not every song he recorded was a classic - although the quality of his work overall is very high. There are a number of songs that are actual masterpieces, and many have been covered by other artists. These are my choices for Nick Drake's  greatest songs.

Time Has Told Me
A slow, flowing tune with a waltzing country feel, this song has been one of Drake's most famous and well-loved songs. Robert Smith took his band's name from the lyric (The Cure) and it has been redone by many, most notably Kelly Willis. It's a love song, but not a simple one - complexity is inherent in the poetry of the words.

River Man
A fiendishly difficult song to play (it's in 5/4 time and standard tuning), Drake's delicate yet insistent finger-picking and the soaring string arrangement are beyond exquisite. And then there are the lyrics - poetry with grace and subtlety. Drake's producer Joe Boyd has stated that he believes Drake knew the masterpiece level of the song, and thought of it as the high point of his first album.

Way to Blue
Another melancholy masterwork, this rhythm-less song features Drake's voice and accompaniment by a classical string quartet - nothing else. Yet it feels like a world is created within the short piece, and it is one of his most incandescent, psychedelic (meaning mind-expanding) songs. The image of "a light among the trees" among others makes the song awe-inspiring.
Northern Sky
A plaintive love song, and inspiration for The Dream Academy's hit song Life in a Northern Town, it's another example of how a few well-chosen images that seem abstract on their own come together in an emotionally compelling whole. Many of his songs seemed to have premonitions or hints of his death - this one asks bluntly, will you love 'til I'm dead?

Pink Moon
The title tune from his third and last album, this one has unfortunate connections to a Volkswagen after being used in a commercial. The album was recorded in a solo minimalist fashion, with Drake's voice and guitar the only sounds - except for a brief piano on this song. It's really a chilling work, if you accept that the pink moon is death personified, coming to get us all.

Which Will
A seemingly slight song, with bare accompaniment and simple lyrics, it still repays study.  And of course, many repeated listening sessions will burn it into your synapses - which will be a good thing. The best cover is by Lucinda Williams.

Time of No Reply
A demo recorded for his first album and unused, this is  a heartbreaking song full of images from nature and humanity. It describes a person who is behind a barrier of some kind, or who has been placed in exile. He says that the time of no reply was calling him to stay - another clear premonition of death. This also the title song of an album of demos and outtakes included on the Fruit Tree box set.

Black-Eyed Dog
One of the last 4 recordings Drake completed before his death in November, done in February of 1974. Full of the ultimate sorrow and yet a longing for an end to suffering, this song is hard to listen to knowing his ultimate fate. As with many of lyrics, the apparent death wish or at least seeing death as a remedy has led some to believe that his death was not an accident. He was a depressed, unhappy man who couldn't find his way in the world, and he probably wanted to leave it. In the end, whether he meant to do what he did or not doesn't matter - the world lost a great artist. And in spirit if not in fact, he belongs in that elite group, the forever 27 club.