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The Monkees‘ “Last Train to Clarksville” appeared on the first album a certain jazz singer ever bought. Subsequently, she covered the track on one of her albums. One of the Prefab Four’s regular songwriters reacted to the jazz cover of the song.

Mike Nesmith, Davy Jones, Micky Dolenz, and Peter Tork wearing blue during The Monkees' "Last Train to Clarksville" era
The Monkees’ Mike Nesmith, Davy Jones, Micky Dolenz, and Peter Tork | Michael Ochs Archives/Getty Image

A jazz singer discussed her history with The Monkees’ ‘Last Train to Clarksville’

Cassandra Wilson is a jazz singer. During a 1999 interview with Bomb, she said the first album she ever bought was The Monkees’ self-titled debut album, which contains “Last Train to Clarksville.” Wilson was asked if she had bought the album because she’d seen the group on television.

“Yeah,” she recalled. “I used to watch The Monkees out of the corner of my eye when I had my piano lessons. Saturdays about three or four o’clock every week, that’s when it would come on, at the tail end of my lesson.”

“My brothers were watching it in the other room, and I’d be really distracted,” she added. “I’d be trying to do my lesson and watch The Monkees.” Wilson said her piano teacher didn’t mind her watching The Monkees because he had such a relaxed approach to teaching. She later included a cover of “Last Train to Clarksville” on her album New Moon Daughter.

Bobby Hart discussed how he felt about some covers of The Monkees’ songs

Bobby Hart co-wrote many of the Prefab Four’s songs, including “Last Train to Clarksville.” In his 2015 book Psychedelic Bubble Gum: Boyce & Hart, The Monkees, and Turning Mayhem Into Miracles, Hart discussed some covers of his songs. “I appreciate hearing my songs in commercials and I’m aware that my lyrics are sometimes used as teaching examples on college campuses,” he wrote. “I get a kick out of coming across stuffed animals programmed to play one of my compositions. 

“I enjoy hearing unlikely song interpretations, including popular bluegrass group The Grascals’ as well as jazz artist Cassandra Wilson’s versions of ‘Last Train to Clarksville,’ the Sex Pistols ‘(I’m Not Your) Steppin’ Stone,’ and J-Love’s and Alicia Keys’ takes on ‘Hurt So Bad,'” he continued.

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How ‘Last Train to Clarksville’ performed on the pop charts in the United States

The Monkees’ “Last Train to Clarksville” was the group’s debut single and first No. 1 single in the United States. According to The Billboard Book of Number 1 Hits, it hit No. 1 on the Billboard Hot 100 for a week.

According to Billboard, the tune was the Prefab Four’s third most successful song. The only two Monkees songs that were more popular in the United States were “Daydream Believer” and “I’m a Believer.” Both of those tracks were No. 1 singles that lasted longer at the top of the chart.

“Last Train to Clarksville” was a hit — and Hart appreciated Wilson’s interpretation of it.