20. 'The Gang Gets Whacked' (Season 3, Episode 12/13)
When Frank decides to teach his younger cohorts a lesson in self-reliance by refusing to keep paying their bills, the gang scatters to find the only kinds of work they're qualified to do — then discovers that even those gigs are too demanding for them. Charlie and Dee become drug dealers, but can't stop getting high on their own supply. Mac volunteers to be a mob enforcer, but ends up cleaning the mafia's toilets. And Dennis agrees to let Frank pimp him out to the ladies at his country club, then finds himself agreeing to degradations he'd promised to avoid. ("No ass-play!" quickly becomes "Do you like ass-play? He'll do anything with the ass.") This is Sunny in a nutshell: a group of luckless, short-sighted slackers who get in over their heads, all because they can't scrounge up enough money between them to keep the lights on.