Robert Boss is a peaceful painter and citizen of Land's End, Kourend. He can be located to the east of the bank, near a tree.
Robert Boss: Talk to the tree, make friends with it.
Player: But I can't reach it...
Robert Boss: You can do anything you want to do. This is your world.
Player: That tree looks lonely...
Robert Boss: I'll give him a friend! Like I always say, everyone needs a friend!
Player: Will you be my friend?
Robert Boss: Well of course! Right after I finish this painting.
Robert Boss: I don't make mistakes, just happy accidents.
Player: How very positive!
His name and appearance is a reference to the soft-spoken Master Sergeant Robert Norman Ross, an American painter, art instructor, and television host most famous for his unique wet-on-wet style of painting showcased in his public broadcast show, The Joy of Painting.
As such, the dialogue interactions with him are common phrases he would use to encourage the viewers throughout each broadcast.