Boy With Two Dogs is a painting by Norman Rockwell. It appeared on the cover of the Saturday Evening Post on September 28, 1929.
It depicts a young Mark Twain-esque boy and his dog stopping to pet Raleigh Rockwell. While the young boy’s demeanor is delightful, and seemingly full of the sweet innocence of youth, Rockwell has provided other visual clues that suggest a more challenging existence.
The young boy’s hat and pants are torn and he is without shoes. His hands are dirty and even his dog appears mangy. He is kneeling beside his trunk and small traveling bag, indicating that he is on the move and all alone, apart from his dog.
This simple interaction with the well-groomed Collie appears to have lifted his spirits and allowed him to momentarily forget his journey and his troubles.