It's pretty easy to jump in anywhere, my first episode was thirty-something, although I remember laughing particularly hard at episode 59, Candy Apocalypse. It's very not safe for work, mind.
The only time I've seen him do that is on Cats Does Countdown, so... kinda? One of them will read out an advert, then they all try to unpack the situation that might lead to someone wanting to sell that particular thing, or request that particular service, or so on. It's funnier than I'm making it sound.