Remembered a D&D story I heard in the 80s. One of the player characters had stupidly and overtly committed a serious crime – had he attacked the King during a formal audience? – and been sentenced to beheading. Letting this happen is never a fun way to end a character’s career, but I believe both the players and the Dungeon Master were quite young.
The day of the execution dawns, the prisoner is taken out to the chopping block in the town square, the executioner steps up with his sword… And the only way this DM knows to handle situations involving swords is the combat rules. Which don’t really offer any details on combatants lying trussed up and face down on the block. Also, the execution victim is quite a high-level character, while the executioner is a basic man-at-arms.
The executioner could barely hit the victim, and when he occasionally did, he took only a small proportion of the victim’s hit points. It took an hour in the game world and endless dice rolling in our world to behead him.
Aardvarchaeology - by Dr. Martin Rundkvist 
Not entirely unrealistic.
https://fof.se/tidning/2010/1/artikel/galgbackens-kvarlevor-berattar
http://www.kbec.se/omtalade-och-minnesvarda-avrattningar
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Was the executioner’s name by any chance Jack Ketch? The execution of Lord Russell in 1683 sounds very much like what this player character went through.
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Ah. I guess the DM missed the rules about ‘Coup de Grace’. They apply to a helpless target. Automatic hit, automatic critical hit.
Or maybe these rules were not present in this D&D’s edition. And to be fait, that would only have solved the ‘hitting’ part, not the ‘has 300 hit points’ part.
And to add to Eric Lund’s post, there have been some real life executions in France as well, which were in essence a one-hour beheading.
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