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 as 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 puzzle 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 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 to 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.

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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.



Default: 363190
Default with Spaces: 147085

NOTES: I’m still doing very little word list work due to other projects but the recent additions to the Oxford English Dictionary reported in the news this week game me the impetus to add the small number of entries on my Notepad. Of the OED additions mentioned in articles the one most favorable to crossword puzzles is rando (60), a term for an unknown, odd, or suspicious person. I was unfamiliar with the term but maybe I’ll start hearing it more now that it has dictionary cachet. I remember seeing the portmanteau term hangry (65) on neologism sites a while back. I suspect that the term, meaning irritable due to hunger, was short-listed by the OED so it could deflate the old “gry” puzzle. I’m only sorry that igry didn’t make it into the dictionary first. Other Notepad additions not related to the OED articles include shade balls (70) (several times I watched that video of the drought-mitigating spheres being dumped into a California reservoir) and Okilly Dokilly (75), a metal band in which all the musicians dress like Ned Flanders.


Puzzle Boat 3 / Pre-Shortzian Puzzle Project


Foggy Brume, publisher of Panda Magazine, has announced October 10, 2015 as the launch date of Puzzle Boat 3. The puzzle adventure will feature “over 100 puzzles, multiple metas, and an overall metameta.” Foggy is currently accepting solving teams with an $80 team registration fee. Recommended team size is 6-8 people. The first two Puzzle Boat adventures were a blast and featured a rich variety of puzzle types. Put together a crew and check this out

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David Steinberg has announced that his Pre-Shortzian Puzzle Project is done! All New York Times crossword puzzles from the inaugural 1942 puzzle through the editorial tenure of Will Shortz have been digitally re-created, edited, and deposited on the XWord Info website maintained by Jim Horne. Congratulations to David for envisioning the project and shepherding it for four years. I will always have a special memory of “litzing” (transcribing puzzles from PDF printouts to CCWIN files) during plane trips, often wedged in an economy section seat with the passenger ahead of me reclining into my laptop screen.

PUZZLE: Unthemely #81



Members of the crossword community have been posting reminiscences, tributes, and expressions of condolence following the untimely death of puzzle legend Merl Reagle on Saturday. I, like many others, regard Merl as an early influence and appreciate his philosophy of crossword puzzles being entertainment first and foremost. I never established a close personal friendship with Merl and only interacted with him a handful of times at tournaments, but he was always warm and and good humored and he offered support of my work. I want to extend my deepest sympathies to his life-partner Marie and the others who were close to him.

Brian Cimmet and Ryan Hecht interviewed Merl at the American Crossword Puzzle Tournament in 2009 and used the interview as an episode of their Fill Me In podcast. I have a copy of that episode in my iTunes library and, listening to it again, am reminded of how articulate and engaging Merl was when speaking about crossword puzzles as a business, as an art form, and as a social community. Here is a link to that episode (thanks to Alex Boisvert who posted in the comments).

REVIEW: Lollapuzzocho Puzzles (Spoilers)


Now that ACPT has moved back to Stamford, Connecticut, Lollapuzzoola is the preeminent crossword tournament held in the metropolitan New York area. The eighth iteration of this annual event organized by Patrick Blindauer and Brian Cimmet was held a few weeks ago and it maintained many of the traditions that go back to original 2008 tournament — it took place in a church on a Saturday in August, it featured a puzzle by Doug Peterson, and so on. The popularity of the tournament is growing as demonstrated by the nearly 200 entrants who competed on-site. With this popularity, the tournament is losing a bit of the deconstructionism and theatrical zaniness of its origins, but the organizers continue to commission puzzles with an anti-establishment bent and wit that counter the more traditional styling of ACPT fare. I ordered the tournament puzzle set to solve at home. I went through them at a leisurely pace rather than with a timer and accuracy check, which was an option for at-home solvers who wanted to post their solving skills and be compared with others. I found the set well-constructed and clever overall. My individual reviews of the puzzles follow. Note: I did not solve Brian Cimmet’s tiebreaker crossword, and while I did solve the Blindauer-constructed puzzle extravaganza that was presented at the tournament I am not including those puzzles in this review.

1 – Stop! by Patrick Blindauer
At least one puzzle in each Lollapuzzoola tournament has a multimedia gimmick — visual or auditory information presented that is presented during the solving session and is clueful to the puzzle in some way. Blindauer’s opening puzzle filled this role at Lollapuzzocho and required solvers to play a game of Red Light, Green Light while completing a puzzle. An audio track was played during the session. When a klaxon sounded all solvers were forced to stop writing (though they could continue to read clues). When a bicycle bell sounded, solvers could resume. Failure to adhere to these traffic signals would result in a scoring penalty. At-home solvers were provided with the audio track to simulate the tournament experience, but I confess that I solved the puzzle without playing it. I’m not opposed to the gimmick as a tournament feature but I also recognize that it basically introduced a memory challenge to the puzzle and going through the motions would only confirm what I already know about my poor memory. The puzzle itself is a good easy fill that is well themed to the stop-and-go gimmick. The octagonal grid suggests stop sign and the long across entries represent different interpretations of the clue {STOP}, INTERRUPT, TRAFFICSIGNWORD, and SAYNOMORE. The long down entry, TOREONESHAIROUT, sure described some of the tournament solvers idling between sound effects. Also of note is this lengthy, explicit clue for the repeater NAIR: {Product whose FAQ asks, “Why can’t I use this on my head, face, nose, ears, nipples, perianal area, or genital areas?”}

2 – The ___ Does Not ___ by Anna Schectman
The 15×15 bar-style grid contains shaded entries in the central row and column that divide the grid into four quadrants. Circled cells in the upper right and lower left mimic the graph plotting of a y = 1/x function. Letters in the circles form the words LIMIT and EXIST, which apparently fill the blanks in the puzzle’s title. Entries that intersect the shaded cells create the words CONTROL, CONFINE, CONTAIN, and CURTAIL. The “origin” cell is empty. I checked the answer key to see if something is supposed to be placed in the cell and discovered that all of the shaded cells were blacked out. So, I guess, the four words that are synonyms of “limit” do not exist in the puzzle for purposes of tournament scoring (?) The mathematical theme (if I am indeed understanding it correctly) is interesting but as a timed tournament puzzle there is a bit too much going on for my taste.

3 – Double Up by Mike Nothnagel
Mike 19×17 puzzle features theme entries that contain a set of double letters shifted backwards one space in the alphabet. So LETTERJACKETS becomes LESSERJACKETS {Inferior outerwear?} and HORSEANDBUGGY becomes HORSEANDBUFFY {Costars of “Mister Ed the Vampire Slayer?”}. The theme is traditional but well executed and the grid contains some good trivia facts that Nothnagel is known for, such as {Where the longest professional baseball game (8 hours and 25 minutes) was played in 1981} for RHODEISLAND.

4 – Going Off the Grid by joon pahk
This puzzle by joon was the hardest of the first-round puzzle but also my favorite. The 16×15 grid is positioned about a row of 16 squares and the puzzle instructions indicate that these extra squares, when filled properly, will reveal the puzzle’s theme. The puzzle contains some moderately difficult clues as well and some clue/entry combinations that make no sense. How does {Block relative} clue AGER? The aha comes when one discovers that the clue/entry pair should have been {Bock relative} and LAGER, but the L was moved from the entry to the clue. This transformation occurs once per column, and the letters involved in the move, when duplicated in the square below the grid, form the phrase LETTERSOFTRANSIT. As with the AGER/LAGER, the letter deletions all result in legitimate crossword entries and the letter additions are cleverly placed in the clues. I especially like {They’re found in latkes} for SURGEONS. Excellent puzzle!

5 – Clone Club by Doug Peterson
The theme entries Doug’s 21×21 are all phrase that suggest a pairing or duplication and the corresponding clues consist of a duplicated word. So, {SPAN SPAN} clues DUPLICATEBRIDGE and {EXPONENT EXPONENT} clues POWERCOUPLE. It’s another traditional theme but the breezy puzzle was an enjoyable way to finish off the first-round set. My only challenge came from the fact that the title reminded me of the 1970s animated series Clue Club, and the theme song earwomed me as I tried to finish the puzzle. Nice non-theme clues include {Flying Solo} for HAN and {Film with the line “A boy’s best friend is his mother”} for PSYCHO.

6 –  Express Finals: Pieces of Eight ???? by Kevin G. Der
I’m a fan of Kevin’s themeless puzzles and can usually get on his clue wavelength. With the difficult Express Division clues in this 15×15 championship puzzle I wasn’t able to finish in the 15 minute time limit allotted to the tournament finalists, but I think I finished it in under 30 minutes based on my personal estimate. The grid is laid out in “pinwheel” fashion creating four isolated mini-puzzles in the puzzle’s corners. Also, the puzzle contains a rebus theme: eight squares contain two letters instead of one, and these letter pairs can be combined into four words that can follow EIGHT to form phrases: MILE, PACK, BALL, and IRON. And the puzzle contains a lot of devilishly hard clues. I was lucky in a few areas, knowing the {“Leave It To Beaver” actor} TONYDOW and immediately seeing through the {Pain application?} as calling for the French word for butter (BEURRE) but I needed some time to suss out {Go from 1st to 3rd, say} as SKIPAGRADE and {Fertility aid since 1951} for MIRACLEGRO. I’m not won over on the idea of using a rebus gimmick in a tournament final, but I relished my slow but sure progression through Kevin’s challenging puzzle.

Please share your thoughts on these puzzles, and insights on the tournament itself if you attended Lollapuzzocho in person.

PUZZLE: Unthemely #80



Over the last few weeks I’ve been leading corporate team-building workshops for Puzzah!, a puzzle room business in downtown Denver. The participants often ask me questions related to my work as a crossword constructor, most commonly, “Do you know Will Shortz?” No one has yet asked me the stereotypical “which comes first, grid or clues?” question. Yesterday a participant asked me about my favorite entry in a crossword I constructed and I mentioned the German word GEMUTLICHKEIT that I used as a seed in an Unthemely puzzle. It’s not my absolute favorite but it illustrated how an unusual word with an interesting meaning is a popular starting point for a crossword constructor. I’ve started thinking about other possible crossword questions that workshop groups might ask and what my answers would be. Of course, it would probably be a better use of time to put together a stock answer about Will Shortz.

Lollapuzzocho / The Horseshoe Letter


Congratulations to Francis Heaney who triumphed in last weekend’s Lollapuzzoola 8 tournament in Manhattan. Congratulations as well to Trip Payne and Erik Agard, who finished in second and third place respectively, and to Simon Porzak, Alex Jeffrey, Seth Kleinerman who took the top spots in the Local Division. I received my solve-at-home copies and solved them on Sunday morning. I wasn’t interest in submitting my times for the leader board. I just strolled through them while providing my own color commentary on my performance. I’ll review the puzzles in a few weeks, but I was pleased with the set and can understand the difficulty that the finalists had with the Express Division clues.

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Christopher King’s latest blog post includes a link to his latest USC Puzzle Hunt titled The Horseshoe Letter. Chris’s previous hunt have required site-specific knowledge to complete some of the puzzles, but this hunt’s puzzles are all general knowledge (or Internet researchable) so he has made the hunt available as a contest for readers. It’s a enjoyable hunt that is well-suited for novice extravaganza solvers: the puzzles are breezy and the meta, while tricky, is gettable. Chris is accepting submissions from readers through August 29.