SF Sketchfest Review: The Crossword Show at the Gateway Theatre, 2/3/23

If you’re reading this, there’s a chance you may already know that those of us who contribute to Spinning Platters are known around here as “music nerds.” While I absolutely identify as such, there’s another term that describes me even better: word nerd. I delight not just in clever wordplay but languages in general, etymology… you name it. So when I heard about Zach Sherwin‘s Crossword Show, which promised a night full of crossword puzzles, trivia, comedy, and fun, I knew I couldn’t miss it!

Last Friday night, I found myself at the Gateway Theatre, waiting for the show to begin. To kill the time, I did what many do these days: I pulled out my phone and played a game. Realizing how “meta” it was to be playing “Crosswords with Friends” while waiting for this particular event, I chuckled to myself, finished my puzzles, and put my phone away. Not long after, host Sherwin was introduced and the night began.

The night’s panelists were Kevin Allison and Kenice Mobley, both of whom said they weren’t exactly cruciverbalists. (Allison explained that he had been more of a “Jeopardy! kid,” while Mobley admitted she had never finished a crossword – but hoped to do so that night.)

As Sherwin began explaining how the show works to the crowd, I scribbled down copious notes. Unfortunately, now that the show is over, I must say that I couldn’t possibly keep up with all of the intricate connections and coincidences Sherwin compiled for “Puzzle No. 5,” which was created by Paolo Pasco. As is the case with most crosswords, the puzzle had a title: “Showdown!” Sherwin explained that he had started this puzzle work on February 4, 2020. Since that was just before the beginning of the COVID pandemic, “Showdown!” was ultimately “two years and three hundred and sixty-four days” in the making.

After showing the blank puzzle grid to the crowd, Sherwin rapped the grid’s clues, starting with the across clues and finishing with the down clues. He also sternly admonished the audience not to shout out any answers – when they want audience participation, they’ll ask for it, thankyouverymuch. (Sherwin even mentioned a possible “stern talking-to” for anyone who dared to break this rule.)

While the panelists began to solve the clues (with help from the audience when they might not know the answer), I began to understand how the show works. Sometimes, panelists simply answer and move on to the next clue. At some point in the show, however, Sherwin would talk about the clue, the answer, or both. Eventually, as the night wore on, he would draw incredible connections between whatever he might be talking about at any given moment to something already discussed earlier. It was a thing of beauty and great detail.

There were several recurring themes of the night, including yams, bengal cats, The Phantom of the Opera, and a minotaur, to name a few. When the panelists came to the clue that said “what many a lessee does less easily since April 2020,” (answer: pays rent), Sherwin paused to plug an important organization, the Los Angeles Community Action Network, encouraging anyone who was able to consider making a small donation to an organization who “organizes people to fight back against oppression.” Nice!

When the panelists had completed the puzzle, the next topic was the theme of the crossword. The longest answers within a puzzle typically have something in common, and if you look at those answers, you may be able to figure out the theme. (Also, interestingly, the themed answers often run across, but Pasco had managed to work them into down clues instead.) The answers were “matted hair,” “pays rent,” and “bengal cats.” What the heck could those things have in common? Well… if you ignore the first word of each of these clues, you’re left with Hair, Rent, and Cats, so suddenly it becomes clearer – they’re Broadway musicals! Even better, Sherwin tied it all back to the beginning of the show by revealing that the title of the puzzle grid (“Showdown!”) referred not just to these Broadway shows but to the fact that the clues to them ran down, rather than across. So fun!

At this point in the show, there was an unplanned interruption over the loudspeaker: a mysterious voice announced that it would be air-dropping a Broadway trivia quiz to Sherwin’s phone. Sherwin insisted that he had no idea what was happening or who the speaker was, but began to peruse the list of the longest-running Broadway shows of all time. Interestingly, the list included Spider-Man: Turn Off the Dark, which I must admit I don’t think I knew existed (but now kind of want to see)…

The mystery list contains 122 Broadway productions, each with at least 1000 performances. At #70 was the show with the longest title (How to Succeed in Business Without Really Trying), while Sherwin brilliantly tied #51 (Crazy for You) to a story he’d told earlier about meeting NFL legend Dick Butkus (#51). In the #28 spot was the current leader in Tony-nominated productions (Hamilton, with an unbelievable sixteen nominations), and finally, the top five of all time were listed as follows: #5: Wicked, #4: Cats, #3: the highest-grossing musical of all time, The Lion King, #2: Chicago, and in the number one spot, we finally learned the identity of the mystery voice who’d taken over the show: The Phantom of the Opera!

The panelists were identified as “dead weight” at this point but were given a last chance to plug any of their projects and say goodbye to the crowd. After they departed, Sherwin asked the Phantom why he was interfering with the show this way. No mention of Phantom in a Broadway musical-themed crossword, of course! This was followed by a brief plot summary of the aforementioned show, which included a few dazzling pangrams like “enjoy box five, squawks crazy, ugly phantom” and “janky chap of sewer maze quite vexed by girl.” Additionally, one of Sherwin’s beloved coincidences turned out to be that Box 5 in the night’s grid was, in fact, empty, as the phantom demands in his own musical. Even better, this was true for box #5 across and box #5 down. Still, the phantom wasn’t happy. He had one of the evening’s bengal cats held “hostage,” threatening to hang him like he hung a stagehand (“strangle and dangle this bengal”).

Sherwin then launched into a series of connections and coincidences that were delightful, connecting Argentine short story writer Jorge Luis Borges, an intricate labyrinth, and a minotaur in ways you have to see (hear) to believe. Sherwin was prepared with visuals, despite his insistence that the phantom’s takeover was completely unexpected and unplanned: a giant labyrinth appearing on the screen displayed the path we’d taken over the course of the evening. Sherwin explained how the labyrinth was hand-drawn (by a woman named Michelle Boggess-Nunley, who currently holds the Guiness World Record for the world’s longest hand-drawn maze). Brilliantly, Sherwin was able to tie the uncommon surname Boggess to another familiar face from earlier in the evening: that of Sierra Boggess, who’s known for playing the role of Christine Daaé in The Phantom of the Opera on Broadway.

After linking the story back to a short but sweet video of a personalized-for-Sherwin pep talk from Dick Butkus, Sherwin was determined to help the crowd find our way out of the labyrinth and back to safety. A video on the screen animated the whole thing, showing a ball of red thread used at the start of the labyrinth, unrolling it as he went so that he could find his way back out easily later. Sadly, when we reached the part of the evening featuring Borges, Sherwin discovered that the evil phantom had cut our thread, potentially leaving us lost in the labyrinth forever. Not to worry, Sherwin would save the day with one last amazing rap that recapped all the unbelievable connections between the topics of the evening, which of course eventually allowed us to find our way back to the start of the labyrinth and into the fresh air of freedom.

I’ve never seen anything quite like Zach Sherwin’s Crossword Show, and so I was a bit unprepared. I thought it would be a fun night of crossword puzzles, trivia, and comedy, but I wasn’t expecting all the phenomenal raps, not to mention how much work Sherwin clearly puts into the puzzle and all the little details he’s able to connect for your enjoyment. It truly was something to behold… and maybe even a little mind-blowing, but I encourage you to see a Crossword Show for yourself to decide!

My souvenir for the evening: a mini take-home version of the night’s crossword puzzle

Stacy Scales

California native. Therapist. Word nerd. Music lover. Linguaphile. Amateur foodie. Basketball junkie. Travel enthusiast.

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Author: Stacy Scales

California native. Therapist. Word nerd. Music lover. Linguaphile. Amateur foodie. Basketball junkie. Travel enthusiast.