The WORST Puzzle Solvers in Pop Culture

We celebrate puzzles here at PuzzleNation, and for the most part, we really try to keep the mood light and the overall tone a positive one. Because puzzles are great, and the people who make them are creative, brilliant, innovative, funny wordsmiths who labor for hours just to bring us some delightful challenges in black-and-white grid form.

As part of the general spirit of PuzzleNation Blog, we’ve been doing a series of posts where we shout-out the best puzzle solvers from the realms of fiction, be it horror movies, classic literature, television, YA novels, and children’s books.

But in all fairness, for some reason, a lot of not-so-great puzzle solvers have also been featured in pop culture. Sometimes, a crossword puzzle is the perfect prop for a bit of comic relief. Other times, the crossword serves as a lens for the character, providing valuable insight into their personality.

And if it’s true that you can’t truly enjoy the sunshine without having experienced a little bit of rain now and then, well, let’s rain on a few characters for the sake of fun, shall we?

Here’s a quick look at some of the worst puzzlers in pop culture.


President Jed Bartlet, The West Wing

Bartlet is an incredibly intelligent and well-read individual, which makes it all the more entertaining to watch him struggle with a crossword during the third-season episode “Dead Irish Writers.” He overthinks one entry, is outwitted by another — coming up with TEA for the clue “It may be bitter” instead of END — and even coloring in a square when an answer doesn’t fit the grid.

That’s not the point of the scene, of course. It’s a showcase of Bartlet’s relationship with his wife and how they’re both confronting a crisis in different ways.

But still… Jed, you’re bad at crosswords.

Bertram Cooper (Robert Morse) – Mad Men _ Season 7, Gallery – Photo Credit: Frank Ockenfels 3/AMC

Bert Cooper, Mad Men

I haven’t seen all of Mad Men, so I can’t be certain, but I only recall one character with a deft hand when it comes to crosswords: Don Draper’s secretary Miss Blankenship. And she serves as the perfect foil for Mad Men‘s worst puzzle solver, Bert Cooper.

One of the top brass at advertising agency Sterling Cooper, Bert is solving a crossword and asks for “a three-letter word for a flightless bird.” Anyone with crossword experience will answer as Miss Blankenship does, with “emu.” Cooper replies, “Nope, it starts with an L,” to which Miss Blankenship responds, “The hell it does.” Clearly Mr. Cooper has already gone astray with this solve.

It’s a funny juxtaposition to have someone in a lower position speak so bluntly to a higher-up, and it also fits perfectly with Miss Blankenship’s abrupt style.

[Image courtesy of SyFy Wire.]

Marjory the Trash Heap, Fraggle Rock

Also known as Madame Trash Heap, this sentient compost heap claims to have all wisdom, and serves as a strange oracle for the nearby Fraggles. Although she possesses some magical powers and her advice usually turns out okay, this doesn’t prevent her from making some pretty silly mistakes. And that includes working on crosswords.

In one episode, Marjory needed an 11-letter word for “life of the party.” Proving both her faulty reasoning and her egocentric view of the world, she confidently claims the answer is her uncle, MAXIMILIAN. (It’s spelled with a silent Q, of course.)

Yes, this is a kids show, and yes, it’s not meant to be taken seriously, but it does make you question her view of the world, no matter how good her intentions are.

[Image courtesy of Screenrant.]

Eugene H. Krabs, Spongebob Squarepants

Mr. Krabs, owner of the Krusty Krab restaurant, is obsessed with money and views pretty much everyone and everything around him in terms of monetary value. This even extends to his recreational activities, as we see in one episode of the show where he is solving a crossword puzzle — well, a crisscross, but this happens in TV all the time — and puts the word “money” as the answer to every single five-letter space in the grid.

Unfortunately for Mr. Krabs, there’s one place in the grid where it wouldn’t work, spoiling the solve. (It is convenient for him that MONEY fits in so many of the five-letter spaces in the grid, though.)

I’m fairly certain Mr. Krabs doesn’t care, but hey, if you’re solving a crossword or a crisscross, you should care. A little. (At least he doesn’t color in grid squares like Jed Bartlet.)

[Image courtesy of Bill Watterson.]

Calvin, Calvin and Hobbes

There’s no denying that Calvin is a very clever boy. He creates games like Calvinball, builds some hilariously morbid snowmen, examines the world with a unique perspective that flummoxes and surprises in equal measure. But one Calvin and Hobbes comic strip reveals that he’s not necessarily a good crossword solver.

In response to the incredibly vague clue “bird,” Calvin says, “I’ve got it! ‘Yellow-bellied sapsucker!'” When Hobbes points out that there are only five boxes, Calvin brushes him off with a casual, “I know. These idiots make you write real small.”

On the one hand, Calvin would have no problem with rebus-style crosswords that put more than one letter into the grid. But on the other hand, no sane constructor would jam twenty letters into five boxes. (Hopefully.)

Walt Tenor, Stuck on You

A pair of conjoined twins in this comedy film from 2003, Bob is the quiet shy brother and Walt is the outgoing one driven to seek success in Hollywood. To further illustrate the differences between the two brothers and the central personality conflict between them, crosswords are mentioned twice in the film.

In both cases, the obvious correct answer — provided by the more timid and thoughtful Bob — comes as a surprise to Walt, who has come up with more inappropriate potential answers. I can’t share either of them with you, fellow puzzler, because we try to keep it family-friendly here on PN Blog, but sufficed to say, the answers tell you what’s on Walt’s mind most of the time, to the detriment of both his relationship with his brother and his ability to actually complete a crossword.

By ignoring the common sense answers and always twisting the clues to suit what he’s thinking about, Walt shares several of the bad qualities seen in other people on this list. He might just be the worst puzzle solver in pop culture.

Can you think of any bad solvers in popular culture that we missed? Let us know in the comments section below. We’d love to hear from you!


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The Best Puzzle Solvers in Fiction

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Last year, we assembled super-teams of the best puzzle solvers in horror films and television respectively. The goal was to highlight characters who stood out, the ones you’d want on your side, because they’re clever, decisive, and immensely capable.

In the third installment in this illustrious series, we turn our attention to literature, seeking out the quickest minds and the deftest problem solvers from the printed page.

Yes, this list will be a bit detective-heavy, since they’re the protagonists most frequently put into situations where puzzly problem-solving becomes synonymous with the character. But we still think it’s a fair representation of the best puzzlers in the medium.


Oh, two quick notes before we get on with the post.

1.) Since both Batman and Sherlock Holmes were listed amongst the best puzzle solvers on television, we’ve opted to exclude them from this entry in order to make room for other individuals. Obviously they still make the cut, but it never hurts to share the spotlight.

2.) Fans of children’s books and young adult novels may be disappointed that the likes of Nancy Drew and Winston Breen didn’t make the list. But that’s for good reason. They’ll be getting their own list in the near future.


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Inspector Morse (Colin Dexter)

[Image courtesy of eBay.]

Detective Chief Inspector Endeavour Morse is the protagonist of 13 novels and dozens of hours of television. This opera-loving detective is famous for enjoying cryptic crosswords, and several of his novels challenge the reader with a crossword clue early on, revealing the answer in a later chapter.

Possessing a keen intellect, Morse solves cases through diligence, intuition, and a near-photographic memory. When you factor in his puzzle skills, you end up with someone who can, for instance, effortlessly realize that the spelling mistakes in a piece of evidence are a hidden threatening message, not mere errors.

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Lord Peter Wimsey (Dorothy L. Sayers)

[Image courtesy of LibraryCat.]

Although investigation is a hobby for Lord Peter Wimsey rather than a profession, that doesn’t make his efforts any less impressive or diligent. He offhandedly solves a cryptic clue for his valet during breakfast, something that will prove helpful later when he has to solve “The Fascinating Problem of Uncle Meleager’s Will.”

Resourceful in the extreme, Wimsey always manages to gather the necessary info to crack the case, whether that requires faking his own death or unraveling an entire cryptic puzzle in order to settle an acrimonious family gathering.

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C. Auguste Dupin (Edgar Allan Poe)

[Image courtesy of Learnodo-Newtonic.]

Perhaps the first literary detective, this creation of Edgar Allan Poe combined a keen eye for observation with an impressive knack for abductive reasoning (inference or making good guesses, as Sherlock Holmes does). Equally at home solving mysteries or chasing forgotten manuscripts, Dupin is the template from which so many crime solving characters sprung.

A master at demystifying enigmas, conundrums, and hieroglyphics, Poe’s creation employed “ratiocination” to place himself in the shoes of criminals and work out not only what they’d done, but where they went after the crime. Surely no criminal mastermind or logic puzzle could withstand the skills of C. Auguste Dupin.

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Mary Russell (Laurie R. King)

[Image courtesy of Goodreads.]

Fans of Sherlock Holmes know that he retired from crime solving and spent his twilight years beekeeping. But worry not, England, because Mary Russell ably fits the role Holmes left behind. As observant and strong-willed as her mentor, Mary is brilliant, proving herself a worthy student for Holmes while still a teenager.

A student of many languages, a theology scholar, and an avid reader, Mary is a fierce and intriguing character who embodies many of the puzzliest attributes of Holmes, but with her own idiosyncratic touches, even managing to resolve lingering threads from some of Holmes’s most famous cases.

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George Smiley (John le Carré)

[Image courtesy of Amazon.]

There are many characters in literature that think ten steps ahead and manage to succeed, but George Smiley is one of the few who does so in believable fashion. The fictional spymaster and intelligence agent may not have Bond’s rakish good looks, but he has the puzzly chops to crack even the most diabolical schemes.

With an encyclopedic knowledge of spycraft and a perceptive mind capable of subtly getting information out of people, George Smiley is a master of looking at the chessboard of international gamesmanship and figuring out the best moves to make, which pieces to sacrifice, and how to read your opponent and outmaneuver him.

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William of Baskerville (Umberto Eco)

[Image courtesy of Amazon.]

Given how many cryptic crossword constructors in England name themselves after Inquisitors, it’s appropriate to find a strong puzzle solver during the time of the Inquisition. Franciscan friar William of Baskerville, often regarded as insightful and humble, refused to condemn a translator as a heretic, deducing that he was innocent. Later, after leaving the ranks of the Inquisition, William is asked to help explain a series of strange deaths at a Benedictine monastery.

William manages to solve the case AND disprove the presence of a demonic force in the abbey, but not in time to prevent tragedy. Nonetheless, his impressive deductions and masterful efforts to unravel the mysteries at the heart of the case — braving labyrinths both real and invented — are key to the novel’s success.

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Sirius Black (J.K. Rowling)

[Image courtesy of Boxlunch.]

Yes, he was a devotee of the Daily Prophet crossword, but it takes more than that to land you on this list. Although reckless at times after a long incarceration in Azkaban, Sirius proved on more than one occasion to have a quick, clever, and strategic mind, a trait shared by many great puzzlers.

He managed to sneak into Hogwarts twice, escaped the infamous Azkaban prison, and deduced where he could find the traitorous Peter Pettigrew. Not bad, especially when you consider the damage Dementors can do to someone’s psyche.

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The Black Widowers (Isaac Asimov)

[Image courtesy of Amazon.]

A fictional dining club (men only, sadly), the Black Widowers often solve problems without ever leaving the dinner table. While many mystery novels walk you through the detective’s deductions and theories at the very end as the crime is solved, each Black Widowers case is solved in front of you, as they ask questions and pose solutions, before the final deduction (and correct solution) emerges.

Combining skills in chemistry, cryptography, law, art, and math, the Black Widowers are equipped to handle every puzzle, even if common-sense solutions occasionally elude them.


Did I miss any world-class puzzlers from famous (or obscure) works of literature? Let me know in the comments section below! I’d love to hear from you!

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