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I have run into two examples of hilarious annotations of games over the years.

One is the "annotation" of the fake "Immortal Overprotection Game" Nimzowitsch-Systemsson, written by Hans Kmoch as a parody of Nimzowitsch's rather arrogant mannerisms.

The other is the "pipe game" Marshall-Burn. Burn always smoked at the board, and Marshall explains in great depth Burn's difficulties in lighting his pipe. At the end, Marshall writes "Poor Burn. I think I swindled him out of that one. If he could only have got his pipe going, it might have been a different story."

I find these both quite amusing. Does anyone know of any others?

Glorfindel
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David Spencer
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    Would this count as amusing annotation of a game? http://www.youtube.com/watch?v=MbX123XtlUs – ETD Jul 18 '12 at 23:34
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    @EdDean, I remember this ad fondly. Quite funny, and I'm always glad to see a chess board on my TV screen. It definitely counts :) – David Spencer Jul 20 '12 at 00:27

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Staunton: It seems utterly impossible for either player to save his game.

Philip Roe
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Best by test - Fischer, waxing poetic on 1. e4

...making Kotov's face quite red. Reschevsky, on burning Kotov with a tactic which exposed a back-rank weakness. I wish I could find the game!

Tony Ennis
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Two examples from Vladimir Kramnik, taken from Kramnik, Vladimir; Damsky, Igor: My Life and Games, Everyman Chess, 2000.

1) A smile in the endgame

Position after 48.Ne5:


    [Title "Kramnik, Vladimir - Ivanchuk, Vasily, Las Palmas 1996"]
    [FEN "8/6K1/7P/4N3/8/k7/8/1b6 b - - 0 0"]

1...Kb4 {The black king is hurrying towards g5.} 2. Ng6 Bxg6 3. Kxg6 {And in view of the variation 50...Kc5 51.h7 Kd6 52.h8=Q my opponent finally resigned.}

Game 151, p. 194

Link to the game

2) In the mystification genre

Kramnik annotates Kramnik, Vladimir - Timman, Jan, Wijk aan Zee 1999 (game 173) on pp. 250-254 in an unusual manner. Her parodies commenters:

I have often begun noticing that the commentaries of certain well-known (and not so well-known) players would be correctly characterised as "frankly hack-work", by no means aimed at searching for the truth.

He then goes on to give 4 reasons, that I paraphrase

  1. Winner wants to make it seem like their opponent "was doomed [...] even before the first move".
  2. Doesn't want to recognize own mistakes.
  3. Doesn't want to waste their time and effort on commentary.
  4. "Anything else."

But he believes that the 3rd reason occurs more often than all the others.

Then comes Part 1 of the commentary (move 1 to 41), followed by Part 2 (moves 26 to 36). Part 2 concentrates on specific moves and is much more thorough. It turns out that annotations from Part 1 from move 26 onwards are parodies of the above mentioned commenters. They are short, but authoritatively sounding, and are refuted in Part 2 which is much more critical of both, Kramnik's and Timman's moves.

After all that has been said, it becomes clear that the play of both players in the game was far from ideal. [...]

Link to the game

Sac Exchange
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This might not be to everyone's taste, but the following annotated game (like the novel it's taken from) is hilarious in it's own way:

Murphy vs. Mr. Endon

Dag Oskar Madsen
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There was a humorous analysis of the old line of the Berlin Defense (where Black plays .. bxc6 and then after e5 retreats with Nd6-b7) by the writer Assiac. It may have been in "The Fireside Book of Chess." The tone of the piece was mocking, putting down how ugly "modern" chess theory was...

Larry Smith
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    Do you have the analysis to share? Otherwise, this isn't much of an answer. – Herb Sep 24 '17 at 05:37
  • I believe you're thinking of Solomon Hecht's article "Telling Off the World Champion", which appears on pp. 56–66 of The Fireside Book of Chess. According to the acknowledgments, it originally appeared in The Gambit in 1930 under the title "How Emanuel Lasker Refutes his own Chess Principles by Wholesale Violations". The opening variation (translated from the descriptive notation) is 1.e4 e5 2.Nf3 Nc6 3.Bb5 Nf6 4.O-O Nxe4 5.d4 Be7 6.Qe2 Nd6 7.Bxc6 bxc6 8.dxe5 Nb7 9.Nd4 O-O 10.Rd1 Qe8 11.Re1 Bc5 12.Nb3 Bb6 13.Nc3. I didn't think it was all that funny. – bof Sep 24 '17 at 08:35
  • I think Assiac is more recent. Note that this is a pseudonyme (Caissa spelled backwards) and was used as "author" for a humorous book about chess. I think it was French and published in the early 2000's, but I wouldn't bet on that. – Evargalo Jul 02 '19 at 07:38
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    @Evargalo Assiac was the pseudonym of Heinrich Fraenkel (1897-1986). He wrote Adventure in Chess, a funny chess book published in 1951 under that pseudonym. – Rosie F Feb 10 '22 at 09:50
  • @RosieF Well, I was off by half a century ! – Evargalo Feb 10 '22 at 10:10