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Tear Jerker: Lil Bush
In "Pooty Poot" when Lil' Rummy impersonates his father. It's actually kind of hard to watch.
Lil' Rummy: What are you looking at? You think you're better then me!? Keep it up mister, I'm getting the iron. No, it's too late!. You should have thought about that before you opened your stupid mouth!"
Hell pretty much any time Rummy talks about his dad. Even though it's Played for Laughs it really makes you feel terrible for him.
The only place his dad can't reach him is the crawlspace behind the water heater.
The ending of "Three Dates". The last shot is Rummy and Cheney cowering in the corner after escaping there dates who had attempted to take advantage of them.