Is "roll deep" an idiom?
"To roll deep" is an idiomatic expression meaning to be wealthy or have a lot of cash. Conan is actually being sarcastic here, as he is counting out one-dollar bills, which are the smallest bills of the American currency. Ex: She's rollin' deep, she even bought a Lamborghini last week. This same expression is also a slang expression meaning to be with a large group of people. Ex: We roll deep at the club. (We went to the club with a large group of people.) Ex: No matter where we go, we roll deep. (No matter where we go, we are always with a large group of people.)