Review: After Endgame is a Comedy Show About Chess and Learning From Your Losses

Author’s note: I had the chance to see a sold-out performance of Kevin James Doyle’s show After Endgame on February 14 at the SoHo Playhouse in Manhattan. I happened to be in town a few days early before the U.S. Amateur Team North championship (our team, Davis and his Spellcheckers did well!), and Doyle’s director Cory Cavin had reached out about opportunities to promote a one-man comedy show about Doyle’s own journey as a chess teacher.

You can learn more about Doyle and the show in his One Move at a Time interview with Bryan Tillis:

Only in New York can you walk down a flight of stairs into a basement bar only to find the tables littered with chess boards, the walls dripping with chess-themed art and three-dimensional display boards, and even a little chess library with classics in descriptive notation. The bartender will even set you up with a good deal on a beer-and-a-shot combo if you ask for the “Pawn to f4.”

This slice of chess-lovers’ heaven is not some gimmicky new pop-up, but rather, we are told, the “masterpiece” of “famed museum curator and designer” Charles “Chuck” Matte. At least, that’s if you believe the playbill for Kevin James Doyle’s immersive, chess-themed comedy show, After Endgame. The 65-minute special runs through March 8 at SoHo Playhouse, and it comes strongly recommended for any wood-pushers in the area.

Doyle is an actor, comedian, and chess teacher who, by his own estimation, has taught over 6,500 chess lessons. As is immediately clear from the second Doyle jumps on stage to a Wu-Tang Clan sample, his approach to teaching chess is steeped in the art of storytelling. Pawns don’t just protect each other, but instead band together to fight off monsters in the forest. He makes it more gripping than this, I promise.

This immersive, engaging approach to chess both serves to reel in the chess novices in the audience and to serve as a taste of what made Doyle’s style of teaching so appealing to one particular investor who serves as the narrative’s antagonist. Without spoiling the show, Doyle finds himself meeting with investors for months in Singapore as a lucrative contract for his chess-teaching company dangles just out of reach.

It’s a comedy, not a tragedy, so Doyle is fine. But it’s a comedy, so something went wrong along the way, too. And this is what the show was really about: what went wrong.

Chess players are always told to review their own games and, especially, to annotate their losses. By talking to your opponent, you can learn how they thought differently than you. By doing this in public, you can get the input of those who might have an outside perspective. By writing these thoughts down, you have an opportunity to challenge your thinking and grow as a chess player.

In the digital age, the art of the post-mortem is not quite extinct, but it is increasingly common to see players finish their games, shake hands, and go off to plug their moves directly into their phone. No conversation with their opponent, no reflection on what they think went wrong, no opportunity for reflection or growth. Just a numerical grade of their accuracy to keep their ego in check or, on rare occasions, to post on social media with glee.

Photo by Josh Goleman

Kevin James Doyle’s comedy show After Endgame is many things: a wild story about overseas investors in a chess education company, a chess lesson for the audience, a self-referential masterclass in storytelling. But, above all else, the 65-minute set is an ode to the post-mortem.

Like most actors-turned-comedians-turned-chess-teachers, his life did not exactly follow his original plan, and he uses this show as a chance to ask what went wrong. The way he answers this question is as entertaining as it is familiar to chess players: here’s a moment where he didn’t follow a principle that he teaches to three-year-olds, here’s a moment where the thought of a big win clouded his judgment, and so on.

The beauty of this show, and what makes it work, is that this reflective, honest, and at times humbling process is presented as an end-in-itself, rather than a mere steppingstone on the way to some other, material success. Unlike so many instances of chess in popular media, this is not a story about a chess prodigy defined by their victories. Rather, it’s an ode to the game of chess as a process with its own ups and downs. The chance to reflect and (maybe) do better next time is not just a steppingstone to the GM title, but its own reward. After all, as Doyle himself notes in his performance, playing chess can enrich anyone's life, but playing chess well is a sign of a wasted life.

Photo by Josh Goleman

Chess is for everyone, and the way Doyle unfolds his own experiences as a teacher serve as a nice example of how skills from chess can make us think differently about our own crafts and careers. So, it’s only fitting that Doyle is also using this show as a sort of fundraiser for The Gift of Chess, which is a self-described “global movement committed to transforming lives through the universal language of chess.” Doyle’s stated aim is to raise $10,000 for the New York-based organization.

After this run of shows at the Playhouse ends on March 8, Doyle has two scheduled performances at the end of the month in Los Angeles. But those unable to make it to either coast need not fear. Several of Doyle’s previous specials are available on Prime Video, and hopefully After Endgame will join them in the future. While you’ll miss out on Chuck Matte’s chess museum/bar, I have to suspect most readers have a similar set-up of display boards and old chess books in their home, so the experience should translate nicely to streaming.