Drake has come to be credited as an influence on numerous artists, including Robert Smith of the Cure, Peter Buck of R.E.M., Kate Bush, Paul Weller, Aimee Mann, Beck, Robyn Hitchcock and the Black Crowes.

With Drake on piano and occasional alto sax and vocals, the group performed Pye International R&B covers and jazz standards, as well as Yardbirds and Manfred Mann songs.

[24] One of his biographers, Trevor Dann, notes that he had difficulty connecting with staff and fellow students, and that matriculation photographs from this time portray a sullen young man.

[25] Cambridge placed emphasis on its rugby and cricket teams, but Drake had lost interest in sport, preferring to stay in his college room smoking cannabis and playing music.

[27] He began performing in local clubs and coffee houses around London, and in December 1967, while playing at a five-day event at the Roundhouse in Camden Town, made an impression on Ashley Hutchings, bass player with Fairport Convention.

[15] Boyd, who had discovered Fairport Convention and introduced John Martyn and the Incredible String Band to a mainstream audience, was a respected figure in the UK folk scene.

[32] Initial recordings did not go well: the sessions were irregular and rushed, taking place during studio downtime borrowed from Fairport Convention's production of their Unhalfbricking album.

Tension arose as to the direction of the album: Boyd was an advocate of George Martin's approach of using the studio as an instrument, while Drake preferred a more organic sound.

Dann observed that Drake appears "tight and anxious" on bootleg recordings from the sessions, and notes a number of Boyd's unsuccessful attempts at instrumentation.

[15] While Kirby provided most arrangements for the album, its centrepiece, "River Man", which echoed the tone of Frederick Delius, was orchestrated by the veteran composer Harry Robertson.

[42] Eventually, in an attempt to bring some stability and a telephone into Drake's life, Boyd organised and paid for a ground floor bedsit in Belsize Park, Camden.

A month after the initial BBC recordings, on 24 September, he opened for Fairport Convention at the Royal Festival Hall in London, followed by appearances at folk clubs in Birmingham and Hull.

[3][46] Disappointed by his debut's poor sales, Drake sought to move away from his pastoral sound and agreed to Boyd's suggestions to include bass and drum tracks.

Trevor Dann noted that while sections of "Northern Sky" sound more characteristic of Cale, the song was the closest Drake came to a release with chart potential.

[44] Soon after its release, Boyd sold Witchseason to Island Records and moved to Los Angeles to work with Warner Brothers to develop film soundtracks.

"[53] Drake delivered the tapes of Pink Moon to Chris Blackwell at Island Records, contrary to a popular legend which claims that he dropped them off at the receptionist's desk without saying a word.

[50] According to photographer Keith Morris, by 1971 Drake was a "hunched, dishevelled figure, staring vacantly...ignoring the overtures of a friendly labrador or gazing blankly over Hampstead Heath.

Robert Kirby described a typical visit: "He would arrive and not talk, sit down, listen to music, have a smoke, have a drink, sleep there the night, and two or three days later he wasn't there, he'd be gone.

"[71] Nick's supervision partner at Cambridge, John Venning, saw him on an underground train in London and felt he was seriously depressed: "There was something about him which suggested that he would have looked straight through me and not registered me at all.

"[72] Drake was a close personal friend of fellow folk musicians John and Beverley Martyn, and visited them regularly when they lived in London and subsequently Hastings.

[84] Drake had been accustomed to keeping his own hours; he frequently had difficulty sleeping and often stayed up through the night playing and listening to music, then slept late into the following morning.

"[89] Boyd wrote that "the roots of Nick’s harmonies" were in his mother's piano playing,[91] which drew from West End acts such as Noël Coward, Sandy Wilson, and Julian Slade.

[91][12] Boyd additionally listed Django Reinhardt, Miles Davis, Bert Jansch, and Donovan as influences and speculated that he was familiar with bossa nova, specifically with the Brazilian guitarist João Gilberto.

Images related to summer figure centrally in his early work; from Bryter Layter on, his language is more autumnal, evoking a season commonly used to convey senses of loss and sorrow.

The release compiled Drake's three studio albums, the four tracks he recorded with Wood in 1974 and an extensive biography written by the American journalist Arthur Lubow.

According to The Atlantic, "The chronic shyness and mental illness that made it hard for Drake to compete with 1970s showmen like Elton John and David Bowie didn't matter when his songs were being pulled one by one out of the ether and played late at night in a dorm room.

[113] Other contemporary artists influenced by Drake include José González,[114] Bon Iver,[114] Iron & Wine,[114] Alexi Murdoch[114] and Philip Selway of Radiohead.

[115] In 2023, Chrysalis Records released The Endless Coloured Ways – The Songs of Nick Drake, a tribute album featuring artists including Selway, Liz Phair and Feist.

[116] In 1994, the Rolling Stone journalist Paul Evans said Drake's music "throbs with [an] aching beauty" similar to the 1968 Van Morrison album Astral Weeks.

[117] According to the AllMusic critic Richie Unterberger, Drake was a "singular talent" who "produced several albums of chilling, somber beauty", now "recognized as peak achievements of both the British folk-rock scene and the entire rock singer/songwriter genre".