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A response to something that happened that in no way could be avoided.
Police officer: The victim was hit by an oncoming car. It was going too fast for him to avoid it.

Police officer 2: ....shoulda rolled.

Or

"Today we will discuss the ways Freddy Murcury could have avoided HIV. Number 1..... shoulda rolled"
by Pandeer Glepstein July 10, 2018
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