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The spider climb spell seems to imply that, normally, you have to use your hands to climb:

A creature gains a climbing speed equal to its walking speed and can move freely along vertical surfaces and ceilings without using its hands.

However, is only one hand needed to climb (allowing one to grapple an opponent with a hand and climbing with the other, kind of like King Kong climbing the Empire State Building with one hand and his feet, and with Ann in his other hand... Also allowing one with only a single arm to climb), or must both hands be used?

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Going by the RAW, there does not seem to be a rule stating that you need both hands free.

According to the PHB climbing rules:

While climbing or swimming, each foot of movement costs 1 extra foot (2 extra feet in difficult terrain), unless a creature has a climbing or swimming speed. At the GM’s option, climbing a slippery vertical surface or one with few handholds requires a successful Strength (Athletics) check. Similarly, gaining any distance in rough water might require a successful Strength (Athletics) check.

However, a DM may decide that holding a struggling creature makes a climb impossible or at least more difficult.

If I was DM, I would probably impose disadvantage on any climb checks made with only one hand available, and maybe give the grappled creature advantage on checks to escape the grapple while the grappler was occupied by a climb.

Keep in mind also that the grappling rules state:

Moving a Grappled Creature: When you move, you can drag or carry the Grappled creature with you, but your speed is halved, unless the creature is two or more sizes smaller than you.

If you have a standard movement speed of 30 feet, no climb speed, and are Medium sized, your movement will be halved to 15 feet while you're grappling anything Small or larger. Then each foot of movement costs an extra foot (or 2 in difficult terrain) while climbing. So, even if your DM rules that you can climb while grappling, you're only going to be able to climb 7.5 feet (or 5 in difficult terrain) while grappling anything but a Tiny creature.

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    \$\begingroup\$ Much in the same way it doesn't say you require two feet for ambulatin'. \$\endgroup\$
    – NotArch
    Sep 24, 2018 at 20:32
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    \$\begingroup\$ It kind of does, actually, if you refer to the Lingering injury rules in the DMG (pg 272-273). "Lose a Foot or Leg. Your speed on foot is halved, and you must use a cane or crutch to move unless you have a peg leg or other prosthesis. You fall prone after using the Dash action. You have disadvantage on Dexterity checks made to balance. Magic such as the regenerate spell can restore the lost appendage." There is no mention of a climbing penalty if you lose a hand, though. \$\endgroup\$
    – user48255
    Sep 24, 2018 at 20:55
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    \$\begingroup\$ I was just being silly, but an optional rule that addresses a more common movement issue doesn't mean that not having an optional rule means something more. \$\endgroup\$
    – NotArch
    Sep 24, 2018 at 21:01
  • \$\begingroup\$ I mean, the quoted text doesn't say you even need any hands... \$\endgroup\$
    – Chris
    Sep 25, 2018 at 15:14
  • \$\begingroup\$ It mentions a check for "few handholds". If you have no hands, there will be no usable handholds; if you have only one hand, there may be fewer usable handholds. (And if you're grappling, rather than just having one hand disabled, personally I would impose further checks or disadvantage.) \$\endgroup\$
    – armb
    Sep 25, 2018 at 16:23
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The fine details on Athletics checks can involve many different considerations and is left to the DM, who might use text from other editions to assist in those considerations.

... for example, 3.5e stated:

You need both hands free to climb, but you may cling to a wall with one hand while you cast a spell or take some other action that requires only one hand.

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Make a Strength check to climb (with disadvantage) looks to be RAI.

There is a character in the published adventure Waterdeep: Dragon Heist (from WoTC) who has had a hand replaced with something (sort of like Captain Hook has a hand replaced by something).

That character has an entry that is explicit: makes Strength checks to climb with disadvantage.

Page 213, Waterdeep: Dragon Heist.

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