Anytime someone talks about Christopher in a less than pleasant manner, you will laugh until your sides hurt (and it's not like this is a comedy series, y'know). Christopher has been referred to as a "constipated owl" and "the only man who can smoke a cigarette in the rain".
The episode "A hit is a hit"
Paulie, when Tony finds out Don Zi Vittorio, the man he wanted make a deal with in Italy is senile:
Paulie: "Ton, you give this guy a golf club, he'll probably try to fuck it."
Pretty much everything involving Paulie Walnuts.
Junior also got funnier as the series and his dementia worsened.
And Janice's religious boyfriend: "Have you heard the good news? He is risen." *falls asleep*
Christopher's drug-fueled eulogy at Livia's wake. Also, his intervention.
Tony's response to Meadow's boyfriend Noah Tannenbaum, AKA Jamal Ginsberg the Hassidic Homeboy, AKA the Oreo Cookie.
Christopher: For all we know he could be out there stalking us.
Paulie: With what? His cock?
Vito is stuck in a boring handyman job, constantly trying to resist the temptation to look at his watch to see when his lunch break is. Finally he convinces himself it's almost noon with the sun's position, but then sees on his watch that it's still more than an hour away and screams "FUCK ME!"
Bobby helping a rapper get some street cred by shooting him, in the ass.
"Hey, you're Annette Benning!".
Silvio flipsout when Matthew Bevilacqua tries to sweep up the crumbs beneath his seat in "The Happy Wanderer". It's pretty epic.
When Paulie first meets Finn, he asks him to clean dog feces off his tires and threatens to knock his teeth out. His facial expression when he finds out he's Meadow's boyfriend is priceless.
