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Playlists: songs about puzzles

June 17, 2026 Peter Kimpton

Pick up the pieces: mixtapes 1000-piece jigsaw …


By Marco den Ouden


I’m a huge fan of puzzles. Every day I do about a dozen of them online including Wordle and its variants, Connections, and The Atlantic’s Bracket City. What I discovered while listening to the nominations for this topic, not surprisingly, is that puzzles in their various forms are a metaphor for life. But we’re going to start off with a song that is a pure expression of puzzle genius. It was the first song that blew me away when I heard it. 

Tom Rosenthal’s Drift Along Small World on the surface seems to be a mellow,  contemplative, wistful tune. And it is that. But watch the video that goes along with it and you will see genius. The video shows a fellow on a train pulling out his cellphone and starting to play a game. The lyrics are all five-letter words and float by in the background, each as a Wordle clue. One is struck by the brilliance of what the writer has done here, but one is also deeply moved by the song itself. These are not random words. They fit into a coherent whole, a song about loneliness. 

Another song that incorporates a puzzle into the song is Anagram (for Mongo) by Rush. Each line includes an anagram. For example:

There is no safe seat at the feast
Take your best stab at the beast
The night is turning thin
The saint is turning to sin

Spanish songbird Juanita Burbano tells us her life is like a crossword puzzle in El Crucigrama. “My life is a crossword puzzle that I can't solve,” she sings. “I love someone who doesn't love me.”

Jethro Tull tells us that: “Your life is a clue in the crossword” in Crossword Puzzle.

There were a number of songs nominated that used jigsaw puzzles as a metaphor. The Katydids sing about a Girl in a Jigsaw Puzzle. She is meek and submissive, never asserting her own desires, yet she and her lover fight again and again. She laments that she’s “just a Girl in a Jigsaw Puzzle and it's hard to finish, when there's something missing.”

One of the most popular yet most frustrating puzzles of the last fifty years was invented by Hungarian Ernő Rubik in 1974 and popularised worldwide in 1980. Athlete use the Rubik’s Cube as a metaphor for life. He is searching for answers in a world that is “too heavy, too big for my shoulders”. But he doesn’t give up. “I'm like a kid who just won't let it go, twisting and turning the colours in rows. I'm so intent to find out what it is. This is my Rubik's cube. I know I can figure it out.” 

Mazes are another popular puzzle, usually done on a large scale, and in North America, corn mazes are common. In Britain they’re sometimes called maize mazes. But mazes made of hedges can be found in larger gardens around the world. The biggest, in China, has almost six miles of pathway. The Coral sing about a maze in Music at Night. “Change in the season comes like a thorn in my side. Lost in a maze, lost in a maze.” 

Riddles turned out to be another popular themes in our exploration of puzzles in song. And even with the seemingly unanswerable riddle known in Buddhist mythology as the koan, we have two songs to consider. 

Aussie troubadour Paul Kelly asks some seemingly unanswerable questions. “How many angels on a pin? How many tears in a bottle of gin?” But the questions that he should have answered were ones he neglected. “How many times did you call my name? Knock at the door but you couldn't get in?” He was Careless and is paying the price. He lost his tenderness, his ability to relate to people. 

But from a song of lament, let’s visit three sisters, one of whom knows the answers to some riddles that seem unanswerable. Anais Mitchell & Jefferson Hamer tell the story in Riddles Wisely Expounded. A stranger comes knocking at the door. The eldest sister let’s him in. The middle sister prepares a bed for him. But “the youngest sister, fair and bright, she lay beside him all through the night”.

In the morning she asks: “Young man, will you marry me?” He says he will if she can answer a series of riddles.

What is greener than the grass?
And what is smoother than the glass?
What is louder than a horn?
And what is sharper than a thorn?
What is deeper than the sea?
And what is longer than the way?

Her clever answers win the young man’s heart and her sisters prepare her for her wedding. How did she answer these riddles? You’ll have to listen to the song! Another song that dazzled me with its cleverness. 

The subject of detectives came up and I initially rejected the idea. I had hosted Detectives as a topic in December 2024. I resisted opening that door. But the more I thought about it, the more it made sense. Detectives solve real life puzzles. They follow the clues to find an answer. And so I have two detective songs in this puzzling list. 

First up is Tavares with Whodunit. Someone has stolen his girl away and he wants to find out who. So he calls on the world’s most famous detectives to find the answer. Next up is Lou Reed with a Dime Store Mystery. The song is contemplative and philosophical and alludes to the last temptation of Christ. But mostly he thinks about his own loss of faith.

I wish I hadn't thrown away my time
On so much human and so much less divine
The end of the last temptation
The end of a dime store mystery.

What really hooked me though was the music. It starts with a haunting slow rhythm played on the bass. Guitar sifts in and then a couple of power chords starts the song rolling with great power. The video is a live performance and worth watching. 

An interesting take on puzzles was a reflection on Alan Turing and the breaking of the Enigma code. Dub maestro Mad Professor tells all about Cracking the Code. 

We close our set with a song about playing cards. Now card games are not puzzles. They take strategy and aim at a definite outcome—winning. But the outcome falls to chance and some skill. But as used by Sting in Shape of My Heart, the cards are a reflection on the riddles and puzzles of life. 

As I noted in a comment on the nomination, award-winning magician Shawn Farquhar used the song as a basis for an astounding card trick. At the end of the playlist I’ve added the video of the trick after the Sting song because how he does this trick is really a puzzle of its own.  

Anagrammatic 13 Across, Down and Beyond A-List:

  1. Drift Along Small World - Tom Rosenthal (severin)

  2. Anagram (for Mongo) - Rush (Uncleben)

  3. El Crucigrama - Juanita Burbano (Maki)

  4. Crossword Puzzle (Steven Wilson Remix) - Jethro Tull (BanazirGalbasi)

  5. Girl in a Jigsaw Puzzle - The Katydids (Fred Erickson)

  6. Rubik's Cube - Athlete (happyclapper)

  7. Music at Night - The Coral (ShivSidecar)

  8. Careless - Paul Kelly (Nicko) 

  9. Riddles Wisely Expounded - Anais Mitchell & Jefferson Hamer (Nicko)

  10. Whodunit - Tavares (pejepeine)

  11. Dime Store Mystery - Lou Reed (tincanman)

  12. Cracking the Code - Mad Professor (Nicko)

  13. Shape of My Heart - Sting (Noodsy)

Baffling Brainteasers B-List:

  1. Jigsaw Puzzle - The Rolling Stones (TarquinSpodd)

  2. Jigsaw Falling Into Place - Radiohead (happyclapper)

  3. Crossword Puzzle - Lynsey de Paul (magicman)

  4. When When When - The Divine Comedy (happyclapper)

  5. Crossword Mamma You Puzzle Me - Frank Crumit (BanazirGalbasi)

  6. County Fair - Joe Walsh (magicman)

  7. Puzzle - NewDad (vanwolf2)

  8. Puzzle With a Piece Missing - Gotye (Nicko)

  9. Riddle I This - Dennis Alcalpone (Nicko)

  10. I Gave My Love A Cherry (The Riddle Song) - Josh White (Nicko)

  11. The Cube - Bo Jenkins (and 3 Year Old Daughter Mandy) (SweetHomeAlabama)

  12. Jigsaw Puzzle of Life - Kate & Anna McGarrigle (TatankaYotanka)

  13. Jigsaw Puzzle - Of Montreal (Uncleben)

  14. Jigsaw - Rufus with Chaka Khan (Fred Erickson)

  15. Four Down and Twelve Across - George Strait (SongBarLandlord)

Instrumental C-List:

  1. Jigsaw Puzzle Blues - Fleetwood Mac (magicman)

  2. King Solomon's Marbles - The Grateful Dead (Chris7572)

  3. Is Not All One? - Tony Scott, Sinichi Yuize & Hozan Yamamoto (Nicko)

  4. One Hand Clapping - Paul McCartney & Wings (Nicko)

  5. Jigsaw Puzzle Blues - Joe Venuti/Eddie Lang Blue Five (Nicko)

  6. Nimrod (Enigma Variations) - Edward Elgar (Uncleben)

  7. Pick Up the Pieces One by One - Above Average Black Band (Nicko)

  8. Puzzle - Passport (BanazirGalbasi)

  9. New Blues Old Bruise - John McLaughlin (BanazirGalbasi)

Ye Olde Guru Pick:

Bracket City Anthem - Bracket City is popular game appearing on The Atlantic magazine website. It was created by Ben Gross. The song references the enigmatic nature of the game and the “Puppetmaster” who controls Bracket City. 

These playlists were inspired by readers' song nominations in response to last week's topic: Solve this one: songs about puzzles. The next topic will launch on Thursday after 1pm UK time.

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In African, avant-garde, blues, comedy, country, dance, disco, drone, dub, easy listening, electronica, experimental, folk, funk, gospel, hip hop, indie, instrumentals, jazz, krautrock, lounge, music, playlists, pop, postpunk, prog, psychedelia, punk, reggae, rhythm and blues, RnB, rock, samba, rocksteady, showtime, ska, songs, soul, soundtracks, traditional Tags songs, playlists, puzzles, Tom Rosenthal, Rush, Juanita Burbano, Jethro Tull, The Katydids, Athlete, The Coral, Paul Kelly, Anais Mitchell, Jefferson Hamer, Tavares, Lou Reed, Mad Professor, Sting, crosswords, The Rolling Stones, Radiohead, Lynsey de Paul, The Divine Comedy, Frank Crumit, Joe Walsh, NewDad, Gotye, Dennis Alcalpone, Josh White, Bo Jenkins, Kate McGarrigle, Kate and Anna McGarrigle, Of Montreal, Rufus, Chaka Khan, George Strait, Fleetwood Mac, The Grateful Dead, Tony Scott, Sinichi Yuize, Hozan Yamamoto, Paul McCartney, Wings, Joe Venuti, Eddie Lang Blue Five, Edward Elgar, Above Average Black Band, The JBs, Passport, John McLaughlin, Marco den Ouden, Marconius
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