According to Buzz Cason, who partnered Bobby Russell in the Nashville-based Rising Sons music publishing firm, Russell wrote both the songs "Honey" and "Little Green Apples" as "an experiment in composing", anticipating a potential market for true-to-life story songs...with more 'meat' in the lyrics [than was] standard" for current hits. Russell wrote "Little Green Apples" for Roger Miller to record and Miller made the first recording of the song on January 24, 1968 in a session at Columbia Recording Studio Nashville produced by Jerry Kennedy. Released as the lead single from the album A Tender Look at Love, "Little Green Apples" afforded Miller his final Top Ten C&W hit at #6 and also his final Top 40 crossover reaching #39 on the Hot 100 in Billboard. In the UK Miller's "Little Green Apples" reached #19 in the spring of 1968 – when it also reached #46 in Australia – and in the spring of 1969 the track returned to the UK chart reaching #39.
Patti Page recorded "Little Green Apples" for her C&W-oriented album Gentle on My Mind whose title cut shared the Easy Listening Top Ten with Roger Miller's "Little Green Apples". Page's version of the latter was released as a single in June 1968 reaching #11 Easy Listening and affording Page the final Hot 100 appearance of her career at #96.
O. C. Smith had recorded "Little Green Apples" at Columbia Studios LA for Hickory Holler Revisited, the parent album of his Top 40 hit "Son of Hickory Holler's Tramp". The track "Main Street Mission" was issued as the follow-up single, but as Buzz Cason recalls "a disc jockey in Detroit played the album cut [by O. C. Smith] of 'Little Green Apples' one morning". That single spin triggered "such a reaction and rash of phone requests [as to] prompt [the deejay] to call Steve Popovich, head of promotion for Columbia in New York [City]", and "Little Green Apples" replaced "Main Street Mission" as Smith's current single. Smith's version was a #2 hit on the Hot 100, behind "Hey Jude" by the Beatles. And likewise peaked at #2 on the R&B chart in Billboard and was certified Gold for domestic sales of one million units. The song won its composer Bobby Russell the 1969 Grammy Award for Song of the Year and the Grammy Award for Best Country Song.