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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1 thought on “The WORST Puzzle Solvers in Pop Culture

  1. Elaine on Seinfeld is doing a crossword in Jerrys apartment. She hasn’t been on a date with a man in quite some time so her memory is lacking due to this distraction. The clue was Winnie the —. She can’t come up with the answer and Jerry tells her Pooh, she just sits and giggles saying poo poo over and over again. They decide she has to start dating again FAST.

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