The Guardian pays homage to Springfield's Finest
You might not expect to see The Guardian talking about The Simpsons very often, and certainly not in the context of "Top 10 crosswords in fiction." But right there in the #1 spot, ahead of crosswords found in Inspector Morse, Martin Amis, and PG Wodehouse, The Simpsons tops them all.
The episode in question is the Season 20 episode "Homer and Lisa Exchange Cross Words," and when I initially watched it four years ago, I had no idea how intricate or deep this episode was. It was inspired by, and riffs off of, the fantastic documentary "Wordplay" which is about competitive Scrabble players. I had just watched "Wordplay" earlier that week, so I was able to appreciate it on that level.
But from a technical standpoint, this may be one of the most elaborate Simpsons episodes ever constructed. It features as guest stars Merl Reagle and Will Shortz, who are true rock stars in the world of crossword puzzles. But more than that; Reagle and Shortz also consulted on the puzzles in the episode itself.
When Lisa becomes obsessed with crossword puzzles (a natural hobby for our brainiac and smartier-pants-than-thou little Lisa), she enters the rabbit hole of crossword puzzlery. She begins to see crosswords everywhere, and we get a glimpse of life from her perspective, with words and tiles superimposed over Springfield, nested within her hopscotch grids, and so forth.
But the episode's crowning achievement may be the finished crossword puzzle that provides a secret clue, a message from Homer to Lisa. Oh and by the way, the crossword puzzle which appears in the episode was a real world crossword puzzle which appeared in the New York Times the day before, secret message and all.
For those Simpsons fans who were also crossword puzzle fanatics, this was no doubt a truly brain-melting experience. One fan said that seeing the crossword puzzle they had completed that very morning was "a little bit scary, actually. Like "did I eat mushrooms and forget about it" scary."
The experience was a dream come true for Will Shortz, who had been a passionate fan of Matt Groening's work ever since Life In Hell, and had been a Simpsons fan since its earliest days. No doubt Shortz's fandom helped inspire him to truly knock this one out of the park, pulling out all the stops to lay the groundwork for a truly outstanding episode.