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.
When your broke as fuck and cant afford to buy a bag a coke, you ask your dealer/and or friend for a Five dollar hollar. Equivalent to a hefty key bump or half a line.
While drunk as fuck at the bar...."Yo whats up man? Lemme get a five dollar hollar real quick"