Since his sad passing on November 25, 1974, Nick Drake’s stature as a musician and songwriter has taken on legendary proportions. Several generations of serious young men have followed in Drake’s melancholy footsteps: quiet, pensive songwriters, intent on delving deep into the gloomy corners of the heart. Today, Drake shows up on almost every list of influential artists of the 20th century. His music still sounds fresh and seems to exist outside of time and space. In late 2007, Universal Records put out a limited edition of Fruit Tree, the long out-of-print boxed set that contains all three of Drake’s albums—Five Leaves Left, Bryter Layter, and Pink Moon—along with a DVD of the biopic, A Skin Too Few. This edition of the box includes a hefty booklet with a loving song-by-song analysis by his producer and friend Joe Boyd; his engineer John Wood; his great friend, Robert Kirby, who arranged his music; and songwriter, journalist, and friend Robin Fredrick. The songs are not remastered or remixed, but they can still break your heart and lift your soul. Sadder still, when Drake died, probably of an accidental overdose of antidepressants, he considered himself a failure.

“Nick was more than a tortured soul,” says Gabrielle Drake, Nick’s older sister and executor of his musical estate. “He was hard to pin down. He was wickedly funny and amusing, serious about his music, and very enthusiastic about all music: classical, jazz, pop, Eastern, folk. He was always searching for new musical experiences. He was a leader and people gravitated to him, but he was reserved and quiet, with an awareness of the absurdity of life; and he had the most infectious laugh I’d ever heard. We heard it less and less as he plunged into his depression. He was a reserved boy and teenager, but to me, he seemed to be quite happy. It was only in the last couple of years that you could describe him [as the moody poet] he’d become.”

Gabrielle went on to become a successful actor, and recalls a normal, happy family life. “We were a close family. I loved my brother very much, but our interests differed. We came at things from a different point of view and didn’t have any particular special rapport the way children in troubled families do. We were both close to our parents. My father was an engineer, and long before any other family had recording equipment, he would record the whole family, particularly my mom, who also wrote songs all her life. We had a huge reel-to-reel tape recorder; where other people might turn on the TV, he’d turn on the tape recorder.” Many of the posthumous recordings of Drake’s early songs are from these homemade family hootenannies.

“The first time Nick came back from France [in the late ’60s] and played his songs for us, we were all amazed and thrilled. My parents and I loved his music. We could never understand why other people did not. We thought maybe it was family prejudice. But he didn’t like touring and didn’t join the publicity machine.”

Gabrielle and Nick shared a flat in London when he was producing Five Leaves Left. “I knew he was recording an album, but didn’t know how far he’d got. He was a very private person. One evening he came into my room and threw a finished copy of the album down on my bed and said, ‘There you are.’ It was an amazing sensation. We were all very proud.”

Five Leaves Left fared poorly on its initial release. Bryter Layter and Pink Moon did no better. Drake became despondent, then depressed. He moved back home with his parents until he died. “We were not told the pills could be fatal,” Gabrielle says. “The pills were supposed to help him, and I think that night he was so low he may have thought, ‘They may kill me or make me better, but it can’t be worse than what I’m feeling right now.’”

Despite their commercial failure, Drake’s albums usually received good reviews. In 1972, British critic Connor McKnight wrote of Pink Moon: “Drake never fakes. The album makes no concession to the theory that music should be escapist. It’s simply one musician’s view of life at the time, and you can’t ask for more than that.”

Kirby arranged Drake’s first effort, Five Leaves Left, giving the melancholy tunes a deep, soulful resonance with dark string charts that anchored Drake’s jazzy guitar work. The album’s opener, “Time has Told Me”, sounds chillingly prophetic as Drake sings, “You’re a rare find / A troubled cure for a troubled mind.” His vocals, hardly more than a whisper, are free of affectation and sound as disheartening as the songs themselves. Even when the playing is sprightly, as on “Three Hours” and “‘Cello Song”, the lyrics are full of images of loss, loneliness, and death. Rarely has a singer made unhappiness sound so appealing. At the time, critics compared Drake’s Celtic-tinged tunes with Van Morrison’s work, but even at his bluest, Morrison’s music is buoyant, where Drake always seems to be on the verge of sinking beneath his anguish. (The title of Five Leaves Left refers to the message commonly included in a package of rolling papers in the ’60s, signifying that there were only five more pieces of paper in the package. Coincidentally, Drake died five years after the release of the album.)

Considering the commercial failure of Five Leaves Left, not to mention Drake’s fragile state of mind, the title of his second album, Bryter Layter, seems morbidly ironic. The title track is a beautiful instrumental blend of pop, baroque folk, and jazz, with Lyn Dobson’s flute adding hopeless, lyrical accents to Drake’s simple melodic line. Kirby’s arrangements here are more up-tempo, with many characteristics of early ’70s British folk-rock, including Gospel-tinged backing vocals on “Poor Boy”, but again Drake’s grim lyrics and his aching delivery imbue the tunes with a distressing emotional resonance. The last song on the album is “Northern Sky”, one of Drake’s most optimistic love songs, with Dave Mattacks playing a gentle bossa nova beat on drums and John Cale adding some classically-influenced keyboard. But Drake still asks, “Would you love me through the winter? / Would you love me ‘til I’m dead?”

Pink Moon is sparse, only Drake’s voice and guitar, with a few piano overdubs here and there. It’s his last and bleakest album. “Know” could be his suicide note, if indeed he did knowingly end his life. A simple repeated guitar line, moaning wordless verses, and a brief chorus, “Know that I love you / Know I don’t care / Know that I see you / Know I’m not there.” The original cover art featured a negative image of Drake’s face that made him look like a smiling ghost. “Parasite” is a wrenching song of self-loathing, the title tune is an ominous song of the coming apocalypse, and “Harvest Breed” is another gentle ode to approaching winter and limitation. The album ends with “From the Morning”, a song of resurrection that’s painfully poignant, knowing, as we do, what comes next.