Following his rise to fame as one of the most successful popular songwriters of the late 1960s, Webb's early singer-songwriter albums seemed almost "deliberately uncommercial". Both of his initial Reprise albums, Words and Music (1970) and And So: On (1971), offered songs that were less pop-oriented and more personal and idiosyncratic. Still, his more conventional ballads put him well within the 1970s singer-songwriter genre. Although these early albums may have been too eclectic for commercial radio—both failed to chart—each received some good reviews. Webb's reputation within the industry was still high, and he had developed a strong fan base by the early 1970s. Although these recordings failed to make it onto radio playlists, he was able to tour with a band and perform to receptive audiences in various cities, especially New York, Philadelphia, and Detroit. In April 1972, Webb performed in London, recording several shows initially considered for a live album, though his poor vocal performances eventually shelved the project. Some of these live recordings were issued in 2004 as part of a limited edition box set.
In his review for Allmusic, Bruce Eder called Letters the "most surprising, diverse, and possibly the most satisfying of all of Jimmy Webb's early solo LPs" and "arguably the best of Webb's solo albums."