I'm going to go with one of the very easy ones to recognize, but hard to pinpoint..
4.
Spoiler: is Sam and Max, season 1. I think it is episode 3, the mole, the Mob and the meatball, but it could also be ep. 2. Situation: Comedy. It's a bit difficult deciphering if there's one or two previous jobs on the sign.
Actually, it's Culture Shock, ep. 1. If I'm allowed to edit my guess. Started it up to check.