Going out on the town and spending money on fun, drinks, women, clubs, cars ect. and holding nothing back.
Male 1: What are you doing this weekend?
Male 2: I am going to Chicago?
Male 1: Are you going to "hoop it up" while you are there?
Male 2: Yes, I am.
Hoop it up means to have maximum fun in an urban environment for one or two days. In other words, spending cash, drinking bottles, pushing hot women and cars and then going back to being a "real" person.
How can "hoop it up" be used?
Person 1: What are you doing this weekend?
Person 2: I am going to Chicago on Friday and Saturday.
Person 1: Are you going to "hoop it up" when you are there?
Person 2: Yes, I emptied my checking account.
Means to go and play basketball on a court, usually in the late afternoon to early evening. Mostly played by middle class men.
Obama: Hey Am I going to see you hoop it up later man?
Emanuel: Yeah yeah, fuck off.