Looks like something from sesame street, Fosters Home for Imaginary Friends, or some obscure kids show...
It's from 'Simon and the Land of Chalk Drawings (hopefully the one's narrated by Mr Dress-up)
I can remember watching those about 7 or 8 years ago with my then 'lttle man' on one of the kid's only TV channels.
I believe it is a Canadian version of a British created cartoon series.