Headcanon time! Since I don’t talk about my headcanons all that often.
As he got older, Kenny would do whatever it took to help his family when money was especially tight, even if he had to sing out on the street. Craig continuously offered him a few dollars here and there, but Kenny would refuse, wanting to earn the money. Whenever Craig caught sight of him singing for a few quarters on a street corner, he’d be sure to pour whatever extra cash he had into Kenny’s hands.