Last Train to Clarksville was written by the songwriting team of Tommy Boyce and Bobby Hart, who also had hits with Chubby Checker and Jay And The Americans; Lazy Elsie Molly for Chubby Checker in 1964, followed by Jay and the Americans' Come A Little Bit Closer, a top ten record later in the same year.
Boyce and Hart produced the songs for The Monkees television pilot in 1966, including doing the singing. Boyce and Hart also recorded vocals and backing tracks for the Monkees debut album (on which Last Train to Clarksville appeared), with the actual Monkees adding lead vocals later.
Recorded at RCA Victor Studio A, Hollywood, on July 25, 1966, Last Train to Clarksville went to #1 on the Billboard Hot 100 chart in the United States, coincidentally knocking another Theme Time play 96 Tears by ? and the Mysterians to the #2 slot.
As Dylan notes on the Trains (#1) episode of Theme Time, Last Train to Clarksville was a disguised protest against the Vietnam War. According to Bobby Hart, "We couldn't be too direct with The Monkees. We couldn't really make a protest song out of it - we kind of snuck it in."