According to Know Your Meme, "Ah Shit, Here We Go Again refers to a memorable scene from 2004 action-adventure video game Grand Theft Auto: San Andreas. Starting in April 2019, the scene gained significant popularity as an exploitable, often used in reference to repeating confrontations, although other meanings can also be derived depending on the context."
Here is the original video from Grand Theft Auto: San Andreas:
The meme can be used in a wide variety of situations. Here are 16 examples: