It actually makes me slightly ill every time he chows down in his videos; I've seen people paralyzed from the neck down that don't slobber and drool as much while eating. I don't think I've ever seen anyone eat in such a way (except Tammy).
You gotta keep in mind that Jack has (probably) never actually had a 'job' - at most, he was radio DJ (and not a very good one). Jack has the mentality of a spoiled preppy bitch and he has never worked for anything substantial, so he can't relate to the staff and can only see them as automatons. His countless Jack on the Go vids provide insight on how poorly he really relates with the staff and how he cannot fathom any mistake that can occur with his order.
Speaking of Jack on the Go, I was looking through his older uploads and found one where he goes to a spa:
Reminder that this vid is 10 years old and takes place in California. It was odd to me because, while Jack still acts like a dumbass (such as spilling his coffee all over the floor), everyone seems a lot happier and easy-going? IDK maybe it's just me but it makes me wonder about what Jack would be like if he hadn't moved to Tennessee.