For each successful songwriter, there are key songs that mark turning points in his or her career. For Jackson Browne, it's possible to cite three early songs as having a major impact on the way his career went. "These Days," written in 1966 when the composer was only 17 years old, is the first song that can be pointed to as being in the familiar Jackson Browne style: introspective, thoughtful, eloquent. "Doctor My Eyes," which appeared on Browne's debut album, Jackson Browne, in January 1972, was his first hit single, the song that most people heard as their first Jackson Browne composition and performance. But "Jamaica Say You Will" can lay claim to being the most significant song in Browne's career development. Browne wrote the song in 1969. It was a subtle depiction of a relationship in which a man finds comfort with a woman, Jamaica, but then is forced to follow her if he wants them to stay together. Though Jamaica was a woman, not an island, the song was full of images of nature by the sea and sailing, and it explored a key dichotomy that Browne would return to -- that between dry and wet. At the end, the singer pledges he will sail with Jamaica "until our waters have run dry." Browne's music had a style complementary to the lyric; it was becalmed, but melodic, not unlike "the rolling seas" mentioned in the words. The result was a highly original love song. Browne had "Jamaica Say You Will" published as part of a co-publishing agreement he signed with Criterion Music in the fall of 1969. More important, he cut a demo of the song that he sent to artist manager David Geffen in early 1970. Geffen threw the package away, but his secretary, finding it in his garbage, was taken with the photograph of the artist that had been included and played the tape. She then got Geffen to listen to the demo and he signed Browne. Geffen began looking for a record deal for Browne, eventually settling on the idea of founding his own label, Asylum, just to record him. Before that happened, however, the Byrds recorded "Jamaica Say You Will" for their Byrdmaniax album, using it as the final cut on the LP released in June 1971. Though people had been recording Browne's songs since 1966, this was easily his most prominent placing yet. The version, sung by Clarence White, was lovely, if somewhat over-produced (strings had been overdubbed on the record without the Byrds' permission), and the album reached the Top 50.
With Clarence White contributing acoustic guitar, "Jamaica Say You Will" was used as the opening song on the Jackson Browne album, gaining extensive recognition when the LP became a hit in the spring of 1972 in the wake of the singles success of "Doctor My Eyes." The Nitty Gritty Dirt Band, of which Browne had briefly been a member, and which had recorded many of his songs, put "Jamaica Say You Will" on their All the Good Times LP, released around the same time as Jackson Browne, and shortly after that it turned up on Tom Rush's Merrimack County. Before the end of 1972 it had also appeared on the self-titled albums by Bonnie Koloc and Sugarblue. In the summer of 1975, Joe Cocker used the song as the title tune on an album and turned in a typically soulful, gospel-tinged rendition in an arrangement that featured a prominent saxophone part and female backup singers.