user396: 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?

user14390: 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...

user1485: 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

user19441: 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

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

user70: 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! 

user13012: Staunton: It seems utterly impossible for either player to save his game.

396: <p>I have run into two examples of hilarious annotations of games over the years.</p>

<p>One is the <a href="http://www.chessgames.com/perl/chessgame?gid=1334664" rel="noreferrer">"annotation" of the fake "Immortal Overprotection Game" Nimzowitsch-Systemsson</a>, written by Hans Kmoch as a parody of Nimzowitsch's rather arrogant mannerisms.</p>

<p>The other is the <a href="http://www.chessgames.com/perl/chessgame?gid=1000105" rel="noreferrer">"pipe game" Marshall-Burn</a>. 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."</p>

<p>I find these both quite amusing. Does anyone know of any others?</p>
 14390: <p>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...</p>
 1485: <p>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:</p>

<p><a href="http://www.chess.com/blog/thompunton/chess-in-literature-murphy-vs-mr-endon-in-murphy-by-samuel-beckett" rel="nofollow">Murphy vs. Mr. Endon</a></p>
 19441: <p>Two examples from <strong>Vladimir Kramnik</strong>, taken from Kramnik, Vladimir; Damsky, Igor: <em>My Life and Games</em>, Everyman Chess, 2000.</p>

<p>1) <em>A smile in the endgame</em></p>

<p>Position after 48.Ne5:</p>

<pre><code>
    [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.}
</code></pre>

<p>Game 151, p. 194</p>

<p><a href="http://www.chessgames.com/perl/chessgame?gid=1060715" rel="nofollow noreferrer">Link to the game</a></p>

<p>2) <em>In the mystification genre</em></p>

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

<blockquote>
  <p>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.</p>
</blockquote>

<p>He then goes on to give 4 reasons, that I paraphrase</p>

<ol>
<li>Winner wants to make it seem like their opponent "was doomed [...] even before the first move".</li>
<li>Doesn't want to recognize own mistakes.</li>
<li>Doesn't want to waste their time and effort on commentary.</li>
<li>"Anything else."</li>
</ol>

<p>But he believes that the 3rd reason occurs more often than all the others.</p>

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

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

<p><a href="http://www.chessgames.com/perl/chessgame?gid=1011520" rel="nofollow noreferrer">Link to the game</a></p>
 70: <p><code>Best by test</code> - Fischer, waxing poetic on <code>1. e4</code></p>

<p><code>...making Kotov's face quite red.</code> Reschevsky, on burning Kotov with a tactic which exposed a back-rank weakness.  I wish I could find the game! </p>
 13012: <p>Staunton: It seems utterly impossible for either player to save his game.</p>
