"Last Train to Clarksville" was the debut single by The Monkees. It was released August 16, 1966 and later included on the group's 1966 self-titled album, which was released on October 10, 1966. The song, written by Tommy Boyce and Bobby Hart was recorded at RCA Victor Studio B in Hollywood on July 25, 1966 and was already on the Boss Hit Bounds on 17 August 1966. The song topped the Billboard Hot 100 on November 5, 1966. Lead vocals were performed by The Monkees' drummer Micky Dolenz. "Last Train to Clarksville" was featured in seven episodes of the Monkees TV show; the most for any Monkees song.

The song, written by the songwriting duo Tommy Boyce and Bobby Hart, has been compared to The Beatles' "Paperback Writer", particularly the "jangly" guitar sound, the chord structure, and the vocal harmonies. The Beatles song had been number one in the US charts three months earlier.

The lyrics tell of a man phoning the woman he loves, urging her to meet him at a train station in Clarksville before he must leave, possibly forever. The Vietnam War was then going on, and what was not made explicit was that the song was about a soldier leaving for the war zone.

It is often said that the song refers to Clarksville, Tennessee, which is near Fort Campbell, Kentucky, the home of the 101st Airborne Division, which was then serving in Vietnam. However, according to songwriter Bobby Hart, it was not specifically written with that town in mind.

Hart said: "We were just looking for a name that sounded good. There's a little town in northern Arizona I used to go through in the summer on the way to Oak Creek Canyon called Clarksdale. We were throwing out names, and when we got to Clarksdale, we thought Clarksville sounded even better. We didn't know it at the time, [but] there is an Army base near the town of Clarksville, Tennessee — which would have fit the bill fine for the story line. 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."

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