Really, that's the only way to ensure that people want to watch and that he'll participate. He's at his most entertaining when he's on an ego trip and we get a look at his thought processes, opinions, and the like. What's tricky is finding a way to accomplish both.
If we want an ego trip, I still say Postal 2. It's ten bucks on GOG right now, and that's including the expansion packs. Plus, you can mod it to hell and back.
http://www.gog.com/game/postal_2_complete
Jay would go bananas for it, and it'd be interesting to see how long it takes before he starts mowing down helpless civilians. My bet is two minutes or less.