Homeless Harold is an orange headed stick first seen in Stick RPG Complete, outside of Sticky's Liquor. later returning in Stick RPG 2. In the first game, you have the option to give him $10, doing so will give you more charm. You can also give him bottles of booze if you have any. He returns in Stick RPG 2, but you can't interact with him. He will still talk to you if you click on him, however. You can find him sitting behind Donut Land and in front of the 11-Seven.
In the seven year gap between Stick RPG Complete and Stick RPG 2, Homeless Harold apparently developed some grade of mental instability, as proven by his speech lines.