Country Dictionary

Short for "would have".

I woulda played fo good.

i would have done it like an animal

eg, i woulda eaten all of audrey’s food, cuz i’m hungry

Short for "would of"

If I didn't get laid I woulda died.

Meaning: would have, could have, should have
A reply you give to a whinging person who is expressing regret for not having taken a particular course of action when the opportunity originally presented itself. They've suffered the consequences and they are possibly fishing for sympathy or simply beating themselves up about it.

It essentially means, "Too late for regrets, you can't change the past, get on with your life, learn from the experience, make better choices in future, stop doing a post mortem on your life."

Brian: If only I'd listened to my folks and hadn't dropped out of school, I could've been someone by now.
Cecil: Woulda coulda shoulda, Brian.

Meaning that it is of no use to dwell on what should have (shoulda), could have (coulda) or would have (woulda) happened/been done.
Said as an attempt to shorten a discussion that focusses on the past, thus providing no solution to an actual problem.

"Man, if only I didn't cum straight in the air, I wouldnt have jizz on my mullet now."
"Shoulda coulda woulda. There are more important things than that. There is more to life than the jizz on your mullet. You're still young, someday you will wash your hair and the jizz will be gone, but your mullet will last forever."

having an opportunity and not taking it, thus regretting it later; usually used when someone is saying to the person who missed the opportunity.

Tom," man, I should have bought that car!"
Jerry," shoulda woulda coulda, but didn't."

Dismissing a something you could've done, instead of dwelling on it

"If I did _____, I would've gotten it."
"Eh, shoulda coulda woulda"