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Jaw-Dropping Puzzles


Patrick Berry’s “Middle of the Road” was presented as one of the pair competition cryptic crosswords at the National Puzzlers’ League convention in July. Patrick later posted the puzzle to his website, allowing access to people who didn’t attend the convention. To say that the cryptic received universal praise is an understatement. The completion of the puzzle tended to inspire not smiles or ovations but stunned silence, a struggle to comprehend the mechanics involved in producing such an elaborate endgame. The typical solver review, expressed during the convention and on social media afterwards, has been some variation of “my jaw dropped.”

Middle of the Road debuted on the heels of a couple of variety cryptics that produced similar reactions, notably Mark Halpin’s “A Deadly Game” and Cox and Rathvon’s “Minor Adjustments.” The conversation surrounding these works started me thinking about the “jaw-dropping threshold” of puzzle creation. What makes a puzzle not simply enjoyable but astounding? The three aforementioned cryptics have some recognizable qualities making them exceptional and I decided to look through my files to find other puzzles exhibiting these qualities and thus attempt to enumerate the mandible-descending stimuli of puzzlecraft.

Note: I will talk about the three aforementioned cryptics and their solutions freely. I will also talk about these puzzles:
Bluebeard’s Castle by Todd Rew (Bartok)
The Cider House Rules by Jeffrey Harris (Jangler)
Color Ado by Mark Gottlieb (Wombat)
Composition by Mark Halpin (Zebraboy)
In a Century of Letters by Kevin Wald (Ucaoimhu) 
Mafia! by Roger Barkan (Anomaly)
Providence Pentominoes Puzzle by Andrew Bradburn (Jigsaw)
Teleportland by Patrick Berry (Trick)
Tourist Spots by Trip Payne (Qaqaq) 
Wordikabe by ?????

Links to all puzzles are provided; in some cases the linked puzzles are scans of my personal copies which may be fuzzy or have the odd erasure mark. You can use the links to familiarize yourself with the puzzles before reading on. 

I decided to look at variety cryptic crosswords exclusively for this article. The variety cryptic is a puzzle type with especially good jaw-dropping potential because constructors may exercise a wide latitude of creative freedom while still upholding basic formal rules. The grid specifications and clue grammar in standard crosswords are constrained and largely demystified among many solvers, such that well-constructed themes and metas are often regarded as merely clever. On the other hand, free-form puzzles as seen in puzzle hunts and extravaganzas can be created with very elaborate structures, but solvers often recognize the liberties of the constructor and have higher expectations. Variety cryptics fall in the sweet spot in which shining examples can elicit amazement for being both ambitious and true to form.

The ten chosen puzzles are not necessarily what I would consider the ten greatest variety cryptics ever, nor are they ten puzzles that would necessarily cause ones’ jaw to drop. Since this topic was inspired by Patrick’s “Middle of the Road” my search for comparable puzzles favored the ones presented at NPL conventions. I’m sure that I would have found fine examples if I had spent more time culling the Cox and Rathvon oeuvre, Tough Cryptics, All-Star Cryptics, and other collections in my files. My choices comprise puzzles that share the following qualities with Middle of the Road.

1. An architectural conception that effects an extremely intricate or nonintutive mechanism
2. A simple, unassuming appearance that nevertheless yields elaborate or exhaustive output
3. A highly elegant re-creation of a cultural artifact or observation within a puzzle context

The Mad Magazine Fold-In had been featured in crossword puzzles before. Eric Berlin included the gimmick in his crossword suite “A Crossword Lover’s Salute to Magazine.” But in “Middle of the Road,” Patrick applied the fold-in mechanism to every element of the puzzle: grid, clues, instructions, and even the title. This thorough approach required some subtle design choices. For example, Patrick needed to choose words carefully for the clues in the third column so that the requisite letters would follow the right side of the fold with minimal horizontal adjustment. Likewise he needed to choose a title font in which a capital letter “M” matched the lowercase bigram “ad” in width. When I talked with Patrick about this puzzle most of our conversation concerned the layout challenge. Patrick used his graphic design skills thoughtfully to create a page both functional and aesthetically pleasing.

Andrew Bradburn’s “Providence Pentominoes Puzzle” demonstrates a similar architectural prowess. I understand that pentomino sets can be combined to form various rectangular forms, but using that process to create multiple, interchangeable word grids, each with readable output, is a daunting prospect. Andrew pulled of the feat with ease and even used a possible obstacle to thematic advantage, i.e. creating an “A” out of a cent sign oriented sideways. Mark Halpin is also a talented artist and graphic designer. His “Composition” doesn’t exploit his layout skills but the Sondheim Review variety cryptic shows his sophisticated touch with grid design. The puzzle ties together the musical and wordplay senses of composition, as a series of letter changes creates a dense column of hat types that bridge horizontally juxtaposed entries. And the changed letters, spelling LOOK I MADE A HAT, quote an admired Sondheim lyric on the casual brilliance of artistic creation. The structure of “Composition” recalls the string of colors in Travis McGee novel titles that winds through Merl Reagle’s “Shades of John D. MacDonald” — a non-cryptic crossword that is certainly a jaw-dropping candidate. “Teleportland” is a variety cryptic that, like “Composition,” is based on a grid design challenge: can a grid be constructed so that every across entry can be divided into two parts and every opening segment matched to a different closing segment to form new words? The answer is yes, if the constructor is Patrick Berry.

Now Patrick will freely admit that the construction of “Teleportland” was a bear and involved a lot of backtracking to complete. But the end product makes the feat look effortless. Likewise “Middle of the Road” does not suffer in the felicity of its grid entries or clues despite the demands of the fold-in gimmick. During the recent NPL convention many solvers compared “Middle of the Road” to a favorite from the 2008 convention “Color Ado.” Mark Gottlieb’s cryptic tribute to the Denver omelet is another masterful representative of the second jaw-dropping quality. The omelet ingredients hidden in the grid are revealed by a set of grid-cell coloring instructions. The instruction to follow for each cell is based on a matching letter in an extraneous clue word. So each extraneous word must have a letter pattern that works with multiple coloring instructions while maintaining a smooth surface sense in the clue. It’s a demanding task but Mark handled it seamlessly. NPL member Ucaoimhu (Kevin Wald) is the master of maximizing variety cryptic answer output. He often comments that if a puzzle is in any way unconstrained then he needs to add another layer of extraction. Trip Payne’s “Tourist Spots” is an Uc-style cryptic presented at the 2010 convention in Seattle. While the puzzle ostensibly celebrates the Space Needle, Discovery Center, and monorail with thematic clue alterations, the real Seattle “spots” hinted by the puzzle’s title are raindrops, and the words in the final punch line INTO EACH LIFE SOME RAIN MUST FALL deftly wind around the X’s (marking the spots) in the filled grid. Every clue performs triple duty to produce a rich tribute to the Emerald City.

The re-creation of cultural artifacts within the context of a variety cryptic is a very common theme approach. Variety cryptic grids have an extremely malleable geometry and can fashioned to suggest any number of artistic works, sporting events, political symbols, and household objects. In some cases the degree of re-creation can cause or contribute to a jaw-dropping response, as in the omelet produced in “Color Ado.” Roger Barkan’s “Mafia!” plays off the classic organized-crime-themed parlor game; a game that, interestingly enough, was the setting of my first encounter with Roger eighteen years ago. Sentimentality aside, the cryptic is an astoundingly elegant re-creation of the game that includes a round table-shaped grid and the isogrammatic POLICEMAN as a key central entry. The re-creation is at times a little too good, with the mafia members given the spot-on names of Don and Tony, but their associated six-letter entries (ENOUGH EARTHY GANDER EFFUSE) that form a Godfather-reference punch line make the puzzle a classic. Dan Katz’s “Wordikabe” also uses a cryptic context to present a different puzzle/game activity: a nurikabe puzzle. The cryptic portion of the puzzle is admittedly ordinary but Katz’s melding of the two puzzle structures is a remarkable inspiration. Todd Rew is both a talented variety cryptic constructor and classical pianist — his “nom” in the National Puzzlers’ League is Bartok. His cryptic inspired by Bela Bartok’s Bluebeard’s Castle is opera in itself, with a “plot” of clue answers winding through a grid representing the floor plan of the title edifice. The richly-detailed cryptic includes mini-puzzles based on the castle’s seven doors and a meta summarizing the opera, archly, as an OLD WIVE’S TALE.

Along with cultural artifacts, jaw-dropping variety cryptics can re-create or present peculiar observations related to wordplay. A superior puzzle exploits the wordplay property for maximum solver appreciation. In “Tourist Spots” Trip Payne noted that INTO EACH LIFE SOME RAIN MUST FALL consists of four-letter words and devised an extraction mechanism to emphasize this revelation. Jeffrey Harris’s “The Cider House Rules” is based on a similar wordplay observation: that the name of the film’s star MICHAEL CAINE consists of the word MAINE, the film’s setting, containing the letters in the word CHALICE, a vessel that could contain cider. Jeffrey could have made a Weekend Edition Sunday challenge out of that observation but instead crafted an amazing cryptic that illuminates the observation by way of an anagram matrix and adds a punch line that references other films. The most jaw-dropping example of a wordplay observation illuminated by a variety cryptic is Ucaiomhu’s “In a Century of Letters…” The puzzle premiered around the time of the crossword puzzle centenary and the grid includes a facsimile of Arthur Wynne 1912 “Word-Cross” puzzle. This grid-design gimmick had been used in several earlier celebrations of the first crossword puzzle, but Uc takes it beyond the realm of possibility by showing that the exterior letters of “Word-Cross” are “Dear Mr. Wald” and that other extractions from Wynne’s puzzle form an apparent correspondence between Arthur and Kevin. The puzzle is literally jaw-dropping and establishes that either Ucaiomhu has the most talented eye for detail in the puzzle industry or that he has access to a time machine.

* * *

As I mentioned earlier, the ten linked puzzles in this article are not necessarily the ones I would consider the ten best variety cryptics. They are simply ten memorable puzzles that exemplify a trio of qualities that tend to produce strong, positive solver reactions. If you want to cite other jaw-dropping puzzles or add to or refine the qualities I mentioned please do so in the comments.


6 thoughts on “Jaw-Dropping Puzzles

    • I don’t have a top ten. It’s too difficult to narrow down and rank all the choices. I just remember enjoyable puzzles and group them in no particular order. Some other variety cryptics in my enjoyment list but not included in this blog post are Cox & Rathvon’s “Celestial Navigation”, Todd Rew’s “Concerto for Orchestra”, Mike Selinker’s “Subway Station”, Roger Barkan’s “From Jersey to Montana”, Uc’s “Every Letter Counts”, and Mark Halpin’s “Missing Pieces”. If I may include my own work I was pleased with how “Hit the Deck!” turned out.

  1. Cant figure out how to fold Middle of the Road puzzle. I have A and B. One drawback is you come so far then blow it at the end.

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