Learn English – Etymology of ‘wipe the floor with’

The phrase originates in Ireland. Donkeys (or "asses" or "jackasses" as they are called in other parts of the world) do not naturally sit down on their rear ends. In fact, it is an extraordinary achievement to get one to do it. "Talking the hind legs off a donkey" is a literal translation of the Gaelic, which actually means "making a donkey sit down on its rear end". Thus, when a person can talk the hind legs off a donkey, they can talk so much that they could even bore a donkey into sitting down.

Matt's idea that the phrase might have a different meaning in each saying seems probable to me.

I've been slightly more successful searching for see a pudding crawl on its own (without the laughing part). And it is a lot more frequent with creep than crawl.

There's a peak in the early 19th century for see a pudding creep because it was used in an essay by Jonathan Swift :

it would vex a dog to see a pudding creep

where it could be understood as "see a pudding go to waste".

The oldest quote I have found is in a 1617 nonsense anonymous verse :

I grant that Rainbowes being lull'd asleep,
Snort like a woodknife in a Lady's eyes;
Which makes her grieve to see a pudding creep,
For Creeping puddings only please the wise.

Here again it's the idea of waste. So how did it become associated with laughter? (A hint of sadism maybe?)

The phrase seems to be British (rather than US), here's an excerpt to what seems to me to be a pastiche from the TV series Star Treck:

"You would laugh to see a pudding crawl..." Spock read aloud, an eyebrow almost rocketing off his face. "...a fascinating image."

Kirk gave him a weird look. "I never thought I'd say this, but that's one of the only phrases I haven't heard Bones say."

"That is hardly surprising, Jim, as it originates in Britain."

It can found in a cockney dictionary and a 2005 excerpt from a web blog:

But then, us Londoners, as my dad used to say, would laugh to see a pudding crawl.