The Monkees — “Shades of Gray”: Brace for the Obscure (60s rock)! — September 14, 2025

THE GREATEST SONGS OF THE 1960s THAT NO ONE HAS EVER HEARD

1,718) The Monkees — “Shades of Gray”

This is “one of [the Monkees’] finest album tracks, ever” (Matthew Greenwald, https://www.allmusic.com/song/shades-of-gray-mt0008175824), written by Cynthia Weil and Barry Mann, with “a singalong chorus that’s as poignant as it is contagious”. (Ed Masley, https://www.azcentral.com/story/entertainment/music/2024/01/07/the-monkees-greatest-hits-of-all-time/72079810007/) Off of Headquarters, the Monkees’ declaration of artistic independence, it “is possibly the most important song the Monkees ever did . . . . timeless”. (thomastimlin1724, https://www.youtube.com/watch?v=D9ZxRjItD1o) It has great emotional resonance — “I just listened to it again (55 years later) and burst into tears. My 14-year-old self thought it was just a nice song and had no frickin idea.” (Gumboz1953, https://www.youtube.com/watch?v=D9ZxRjItD1o) It “was supposed to be the single from Headquarters, but RCA nixed it, saying the Monkees don’t do protest songs.” (rjmcallister1888, https://www.youtube.com/watch?v=D9ZxRjItD1o).

Matthew Greenwald writes:

Despite the fact that the Monkees gained creative control of their recordings from Don Kirshner at the beginning of 1967, they very smartly were not opposed to utilizing the Brill Building writers who had been under Kirshner’s rule earlier. “Shades of Grey,” a fabulous Barry Mann/Cynthia Weil ballad, was perfect for both the group and the time. A poignant and beautiful pop statement about the loss of innocence, the song makes references to both the civil rights struggle as well as the Vietnam War . . . . Tastefully arranged with a fine vocal duet between Davy Jones and Peter Tork . . . .

https://www.allmusic.com/song/shades-of-gray-mt0008175824

Ed Masley adds:

This is as pretty a song as the Monkees would ever record, a richly orchestrated ballad with stately piano by Tork (who shares the vocal spotlight with Jones) and session players fleshing out the understated chamber-pop arrangement on French horn and cello. The song was written by one of the Brill Building’s more inspired duos, Mann and Weil, as a bittersweet reflection on the changing times that finds them pining for simpler days when “it was easy then to tell right from wrong.” There are no easy answers here . . . .

https://www.azcentral.com/story/entertainment/music/2024/01/07/the-monkees-greatest-hits-of-all-time/72079810007/

Andrew Sandoval tells us that:

Headquarter’s finest showcase of the group’s newfound arrangement expertise. “We created that stuff from scratch,” says [Peter] Tork. “Mike wrote the horn and cello parts, sang them to me, and I notated them. I was also really pleased with that little piano introduction I wrote. We were just thrilled to death with that song.”

liner notes to the CD reissue of Headquarters

As to Headquarters, Tim Sendra writes:

After the release of More of the Monkees, on which the band had little involvement beyond providing vocals and a couple Mike Nesmith-composed songs, the pre-fab four decided to take control of their recording destiny. After a well-timed fist through the wall of a hotel suite and many fevered negotiations, music supervisor Don Kirschner was out and the band hit the studio by themselves. With the help of producer Chip Douglas, the band spent some time learning how to be a band . . . and set about recording what turned out to be a dynamic, exciting, and impressive album.

https://www.allmusic.com/album/headquarters-mw0000653823

Here are the Will-O-Bees:

Here is Sandy Posey (see #1,154):

Here are the Sons of Champlin:

Here is P.K. Limited:

Here are the Newcomers:

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