Old drama anime about a dog and a kid
Nobody's Boy Remi fits quite well. It's a drama anime from 1977 and is indeed very sad.



At around the midway point in the series, his guardian dies along with several of his animals, leaving him to fend for himself. He is always accompanied by his loyal dog Capi and has a monkey named Joli-Cœur. Hulu Plus has the complete series if you're a subscriber.

The anime was remade in 1996 as Nobody's Girl Remi (switching the gender of the main character), but it isn't as highly regarded.