Kvatch of The Hoax Hotel is masterful at playing rubes who fall for online scams. In this gem, he keeps an "FBI agent" named "Josh" on the line for nearly 22 minutes, riling him up until he's "the angriest scammer I've ever called."
The fact that "Josh" keeps working him for so long makes it seem that "Josh" is used to getting a lot of dumb questions. What's remarkable is how Kvatch teases just enough forward momentum each time to keep "Josh" on the hook.
Bonus video: another instant classic from last summer: