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(Inspired by this question about adamantine armor)

The item description for adamantine armor states:

While you're wearing it, any critical hit against you becomes a normal hit.

The item description for a vorpal sword states:

When you attack a creature that has at least one head with this weapon and roll a 20 on the attack roll, you cut off one of the creature's heads. The creature dies if it can't survive without the lost head.

A roll of a natural 20 is also a critical hit, which adamantine armor reduces into a regular hit. So, if a creature wearing adamantine armor is hit by such an attack from a vorpal sword, does the adamantine armor also prevent the beheading property of that sword?

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    \$\begingroup\$ Are you attacking a manxome foe? Did it come whiffling through the tulgey wood? \$\endgroup\$ – Robert Columbia Oct 20 '18 at 15:42
  • \$\begingroup\$ Oh, geez, this question gives me flashbacks to 3.0, where Vorpal activated on a crit and there were all these keen-vorpal-scimitar-prestige class builds to try to expand the crit range until you could lop heads on a 15+. Ever since 3.5 it's been "on a natural 20" instead! \$\endgroup\$ – Darth Pseudonym Oct 22 '18 at 1:46
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No, the creature still loses its head

The effect of the vorpal sword is explicit:

...and roll a 20 on the attack roll, you cut off one of the creature's heads.

This wording in the item description implies that the beheading effect is completely distinct from the effect of a critical hit. Reducing the result of the attack from a critical hit to a regular hit doesn't change the fact that the attack rolled a natural 20. So, adamantine armor won't stop the sword from beheading you.

Other weapons with similar wording behave the same

Items like the sword of sharpness and mace of smiting have similar wording. As such, they work identically. If you roll a natural 20 on your attack roll, then you apply the extra effects from the item, regardless of whether or not the result is a critical hit.

However, effects that apply "when you score a critical hit" are negated

For example: The nine lives stealer description states:

If you score a critical hit against a creature that has fewer than 100 hit points, it must succeed on a DC 15 Constitution saving throw...

In this case, when the attack scores a critical hit against you, the critical hit becomes a mundane hit. So, the extra effect from this kind of weapon doesn't apply since the attack didn't score a critical hit.

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    \$\begingroup\$ I think the Vorpal has such a wording to avoid balance problems with Champions, and the Adamantine armor is meant to protect against it, but only a tweet could prove me right. \$\endgroup\$ – András Oct 20 '18 at 14:23
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    \$\begingroup\$ Crawford confirms this interpretation about the vorpal sword's "natural 20" requirement here and here. \$\endgroup\$ – V2Blast Oct 20 '18 at 17:26
  • \$\begingroup\$ @V2Blast I am talking about a confirmation of Adamantine. I think Adamantine is meant to protect against Vorpals, but Champions are more common, so they chose the lesser evil. \$\endgroup\$ – András Oct 20 '18 at 19:46
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    \$\begingroup\$ @András, a Vorpal Sword is a legendary item, while adamantine armour is an uncommon item, so I would assume the opposite: the vorpal sword would still work, by the disparity in power level. If they had intended the vorpal sword to be blocked by adamantine armour, they probably would have written a clause saying something along the lines of 'creatures immune to critical hits are unaffected by this effect'. The negation of critical hits in general, not counting the niche case of vorpal swords, is sufficient for an uncommon item. But this is now delving into opinion. \$\endgroup\$ – BBeast Oct 20 '18 at 20:48
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    \$\begingroup\$ @András: I was "confirming" the answer, not your comment. I don't think adamantine armor is meant to protect against vorpal weapons. \$\endgroup\$ – V2Blast Oct 20 '18 at 21:40

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