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1.
The Michigan-based pizza chain Little Caesars has a promotion going where you can get a large pepperoni and cheese pizza for $5.00 without having to call ahead and order it. This pizza is officially called a "Hot-and-Ready," but this is Detroit, so it is commonly known as a "five dollar holler," optionally pronounced "five dolla holla," but you probably shouldn't call it that if you're white (unless you are trying to be ironic).

Five dolla hollas are not very good, as far as pizza goes, but they are still a favorite of poor high school and college students because they are a cheap way to feed people at a party.
Person A: Hey, can I bring a few extra friends tonight?

Person B: Sure, if you grab a five dolla holla on the way.
by Tripzy May 29, 2006
 
2.
A small bag of marijuana sold for $5. The five dolla holla is usually just enough to be rolled up in a cigarello.
Ron: Hey you got that wrap?
Randall: You got that holla?

Pat went next door to pick up a five dolla holla.
by J Merc March 19, 2007