Chris Rock joked that Bill Gates would jump out the window if he woke up with Oprah’s money. Like most comedy, it’s funny because it contains a nugget of truth.
There is no objective level of wealth -- everything is just relative to something, or someone, else. That means a billionaire can feel poorer than someone with infinitely less money.
This episode tries to create a spectrum of wealth based on the quality of your life, feelings, and social circles, versus measuring it on money alone.