Season 3: Episode 54: Mr. Big Shot
When Greg and Kim plan a family trip to Lake Tahoe with the Hughes, Greg remembers a classy restaurant in the area called The Pinnacle Room that his well-to-do uncle always used to tell him about. As he considers eating there a status symbol, it's a big disappointment when Kim tells him they can't book two rooms in the restaurant's lodge, as it's out of Jimmy's and Christine's price range. On the trip, Jimmy is equally irritated when he realizes Greg took a bigger room for himself. After Jimmy puts him on the spot, Greg admits that he took it on purpose because he's always felt held back on account of Jimmy's lack of money. But after a disastrous meal with Kim at the stuffy, snooty Pinnacle Room where everything that can go wrong does go wrong, Greg sees firsthand that the humble life Jimmy lives ain't so bad.