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how much wood would a woodchuck chuck if a woodchuck looked like you? 

JJ’s insult to Ethan. Basically ridiculing his obesity. Wood chucking is done with the mouth of a woodchuck, hence has a connection to eating
How much wood would a woodchuck chuck if a woodchuck looked like you? Quite a lot, apparently

How much wood can a woodchuck chuck if the woodchuck looked like you 

Ok you must have listened to KSI ft. Ricegum's new song before looking this one up. Fair enough !

So this one was directed at 'Ethan', one of the Sidemen members known as "Behzinga" and it's basically KSI asking Ethan how much wood can a woodchuck, CHUCK, if the woodchuck looked like him, which means if the woodchuck was FAT like Ethan.

So basically he's calling Ethan fat... From the start KSI seems to sum up the whole song !

I have a feeling that the 'Yo Mama' channel would like these fat jokes.
JJ : How much wood can a woodchuck chuck if the woodchuck looked like you ?
Ethan : Idk, if you're calling me fat are we counting the fat in your tits ?
Supa Hot Fire and his crew : OOOOOOOOOOOOOOOOOOOOOOH

Checkalook 

Ill have to checkalook at that later
Checkalook by Whogivsafux October 4, 2013

checkalook 

Yo man, checkalook at that booty!
checkalook by Jimmy Pierce November 9, 2005