I started a thread like this around 6 months ago, but since then I've seen season 3 and it's worth revisiting.

My favorite scene is still from season 1 when Tony is visiting Jackie Aprile in the hospital, and that "nurse" comes in to check his "vital signs." Then her breasts pop out of her shirt while they're pressed against his face and then Jackie realizes that she's no ordinary health care provider.

Another favorite is when Tony is running the executive card game and Matt Bevilaqua is trying to sweep up the mess underneath Silvio's chair. Then an annoyed Silvio tells Matt to leave the cheese there. He says something about how he stuffs cheese in his socks so it smells like his sister's crotch or something along those lines.