Apart from being used to describe a stupid and awkward person, the term "Chucklehead" may also be used as a term of endearment. Usually used for friends with poor communication skills, that arrive late to your social gatherings, that are ignorant and oblivious, that have trouble forming sentences with correct subject/verb agreement, and that are just plain stupid.
Bob just called,he's lost in your neighborhood and is going to be late...what.a.chucklehead
by The King of the Chuckleheads May 14, 2011
Someone who laughs at own jokes in order to get others to laugh along with them. Usually these are clownish characters many find unfunny.
"Boy that Jay Leno sure is a chucklehead! That last bit was not even funny and he's chuckling, bouncing his head around like a moron"
by chuck l. head October 26, 2008