An old saying in the stand-up comedy world, typically used as a way to brag about how well one did in their stand-up set. Can also be used as a way of casually bragging about how well one does something more generic. Frequently shortened to "stackin'" or "stacking" or "stacked."
Used as a compliment or observation for a funny person that causes many breaks in between telling jokes, because people keep laughing and cheering. When you are telling jokes and you get an Applause Break after Applause Break, you start Stakin' those Breaks.
I went to a stand up show and the guy was so funny. People kept laughing and clapping. I think he had an applause break that lasted over half a minute. He was Really Stackin Breaks in there.
Someone who is addicted to obtaining money and building wealth. A money addict and fanatic. Breadheads often work more than one full-time job, and some even participate in illicit activities to "obtain the bread".