Donovan was born in Maryhill, Glasgow, the son of Winifred (née Phillips), a factory worker, and Donald Leitch, a Rolls Royce factory employee. He contracted polio as a child and the disease, and subsequent treatment, left him with a limp. In 1956, his family moved to Little Berkhamsted near Hertford, England.
Influenced by his family's love for Scottish and English folk music, he began playing guitar at 14. He enrolled in art school but dropped out soon afterwards, determined to live out his beatnik aspirations by going out on the road. In 1963, he took a trip to St Ives with Gypsy Dave and other friends from Hertfordshire.
Returning to Hatfield, he spent several months playing in local clubs, absorbing the music of the British folk scene around his home in St Albans, learning the crosspicking guitar technique from such local players as Mac MacLeod and Mick Softley and writing his first songs.
In 1964, he travelled to Manchester with Gypsy Dave, then spent the summer in Torquay, Devon. In Torquay he stayed with his old friend and guitar mentor from St Albans, Mac MacLeod, and took up busking (street performing), studying guitar, and learning traditional folk and blues songs.
In late 1964, he was offered a management and publishing contract by Peter Eden and Geoff Stephens of Pye Records in London, where he recorded a 10-track demo tape (recently rediscovered and released on iTunes), which included the original recording of "Catch the Wind", his first single, and "Josie". The first song revealed the influence of Woody Guthrie and Ramblin' Jack Elliott, who had also influenced Bob Dylan. Dylan comparisons followed him for some time. In an interview with KFOK radio in the US on June, 14th 2005, MacLeod stated: "The press were fond of calling Donovan a 'Dylan Clone' as they had both been influenced by the same sources: Ramblin' Jack, Jesse Fuller, Woody Guthrie, and many more."
While recording the demo, Donovan befriended Brian Jones of The Rolling Stones, who was recording in a nearby studio. Coincidentally, he had also recently met Jones's ex-girlfriend Linda Lawrence. The on-off romantic relationship that developed over the next five years was a pivotal force in Donovan's career. Linda exerted a huge influence on Donovan's music but she initially refused to marry him and moved to the US for several years in the late 1960s. She eventually relented however and they married on 2 October 1970 at Windsor Registry Office. Although Donovan had other relationships—one of which resulted in the birth of his first two children, Donovan Leitch, Jr., and Ione Skye Leitch—he remained strongly drawn to Linda, and she became his muse. His confused feelings about her inspired dozens of songs, including "Legend Of A Girl Child Linda", "Sunshine Superman" and many others.
In the first week of May 1965, Donovan met Bob Dylan, then touring the UK, in Dylan's suite at the Savoy Hotel in London. The music press had made much of the supposed rivalry between the two, and of Donovan's alleged aping of Dylan (similarities also noted by Brian Jones of the Rolling Stones), but the meeting went well and Dylan later told Melody Maker: "He played some songs to me ... I like him ... He's a nice guy." The Melody Maker report also noted that Dylan had mentioned Donovan in his song "Talking World War Three Blues" but that the crowd had jeered when Donovan's name was mentioned, to which Dylan had responded backstage: "I didn't mean to put the guy down in my songs. I just did it for a joke, that's all."
The meeting was captured in a documentary by D.A. Pennebaker, who was filming Dylan's Spring 1965 tour, and part of the event was included in the documentary Don't Look Back, although Donovan's management reportedly refused to allow journalists to be present, stating that they did not want "any stunt on the lines of the disciple meeting the messiah".The director later recalled an embarrassing encounter:“
Of course, when Donovan met him he was very excited and decided to play something for him. Dylan said he liked Catch The Wind, but Donovan said, I've written a new song I wanna play for you. So he played a song called My Darling Tangerine Eyes. And it was to the tune of Mr Tambourine Man! And Dylan was sitting there with this funny look on his face, listening to Mr Tambourine Man with these really weird words, trying to keep a straight face. Then Dylan says, Well, you know, that tune ... I have to admit that I haven't written all the tunes I'm credited with but that happens to be one that I did write! I'm sure Donovan never played the song again! ”
In an interview for the BBC in 2001 to mark Bob Dylan's 60th birthday, Donovan acknowledged Dylan as an important influence early in his career while distancing himself from the "Dylan clone" allegations:“ The one who really taught us to play and learn all the traditional songs was Martin Carthy—who incidentally was contacted by Dylan when Bob first came to the UK. Bob was influenced, as all American folk artists are, by the Celtic music of Ireland, Scotland and England. But in 1962 we folk Brits were also being influenced by some folk Blues and the American folk-exponents of our Celtic Heritage...Dylan appeared after Woodie [Guthrie], Pete [Seeger] and Joanie [Baez] had conquered our hearts, and he sounded like a cowboy at first but I knew where he got his stuff—it was Woodie at first, then it was Jack Kerouac and the stream-of-consciousness poetry which moved him along. But when I heard Blowing In The Wind it was the clarion call to the new generation – and we artists were encouraged to be as brave in writing our thoughts in music...We were not captured by his influence, we were encouraged to mimic him—and remember every British band from the Stones to the Beatles were copying note for note, lick for lick, all the American pop and blues artists—this is the way young artists learn. There's no shame in mimicking a hero or two—it flexes the creative muscles and tones the quality of our composition and technique. It was not only Dylan who influenced us—for me he was a spearhead into protest, and we all had a go at his style. I sounded like him for five minutes—others made a career of his sound. Like troubadours, Bob and I can write about any facet of the human condition. To be compared was natural, but I am not a copyist.