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"Tear Drop City" is a single by the Monkees released on February 8, 1969 on Colgems #5000 recorded on October 26, 1966. The song reached number 56 on the Billboard chart, and number 37 on Cash Box. The lyrics are about a man who feels low because his girlfriend has left him. Written by Tommy Boyce and Bobby Hart, it was the first single The Monkees released as a trio (Micky Dolenz, Michael Nesmith, and Davy Jones; Peter Tork departed December 1968). Micky Dolenz performed the lead vocal. Boyce and Hart produced and arranged the song.
The flip-side was "A Man Without a Dream", with Davy Jones doing the lead vocal, and it hit no.127 on the Cash Box chart.
Both single sides were from the album Instant Replay.

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