a definate start....
as jinchu said, below: this could turn into something nice with some more work put into it!
add more paintings in the same genre to make a longer walk way, add a sad, slow tune to it (make sure it's a good tune, because the music will carry most of this film), let him go slower, so we can actually have a good look at him and realize how sad it is. Change his coat color to match the brown hues all around him, right now he's too... blue... Take the 'happy bill wray day' and also turn it into a more brownish color, you have a great background to work with, play with those browns!