[1][2] In February 1970 he recorded a demo of the song, with Glenn Frey, Ned Doheny and JD Souther backing him.
[2] Allmusic critic William Ruhlmann described the song as "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.
He continues: "When I created the fable of this girl who lived by the sea and whose father is a captain, and eventually she would be taken away and go sailing off, I wanted to hide in the relationship.
Browne plays his voice off the piano's restrained tone, soaring up from his own basically understated vocal in mid-verse and chorus.
This underplaying of mood lights Jackson's simple but evocative images with a muted radiance that aurally captures the look of McCabe and Mrs. Miller.
Naturally, Browne's single-minded delivery drives the tension to even greater heights, and the song soars.
[8] Glide critic Lee Zimmerman rated it as one of 10 Jackson Browne songs that should have been a hit, saying that it "provided a universal connection, dwelling on memories of times well-spent, when trouble and turmoil were displaced by idyllic innocence" and that "few [songs from Browne's debut album] equalled it as far as those longing sentiments were concerned.
[8] According to Byrds' bassist Skip Battin:We had done one dynamite cut of "Jamaica Say You Will", which Jackson Browne had played piano on, and it was not even used.
He had come in and taught us the song and Gene [Parsons], Clarence [White], Jackson and I laid down this beautiful track, which was really hot and very tasty, but for some reason it was considered the demo.
"[11] Greenwald praised the vocal arrangement and production, and said that "although the band wasn't happy with producer Terry Melcher's decision to add strings and horns to the track, it has aged quite well.
"[11] Uncut critic Jason Anderson felt it was one of the strongest cuts on Byrdmaniax, particularly noting the "familiar vocal harmonies.