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1.
"Chip on his shoulder" commonly refers to someone who has a self-righteous feeling of inferiority or a grudge. An example would be someone always bringing up how they are or were disadvantaged in some way.
Person 1:"I was raised in a working class family with no luxuries"

Person 2:"But now you're a millionaire..."

Person 3:"Don't worry about him mate, he's just got a chip on his shoulder."
by ElectricFishy August 12, 2008
219 81
 
2.
Comes from when people spent more time around animals specifically horses. It refers to when someone refuses to do what they are told because the person in charge is incompetent.
A horse was refusing to do what it was told so a veterinarian was called in. The veterinarian examined the horse and noticed a chip of flesh was removed from the front shoulder of the animals leg (chip on his shoulder). As it turned out when the owner was drunk he walked the horse into the side of the barn door. Now the horse refuses to obey.
by fudmitri November 24, 2011
25 68