> "What if I made the worlds worst DRM and then sued everyone who bypassed it?"

Sklyarov was taken to court, and ~I believe is still in jail~, for bypassing Adobe's use of the amazingly secure ROT13 cypher.

EDIT: Charges were dropped a year later, because of the insanity of charging someone for using such an insecure mechanism. But only after both the EFF and Adobe came out in support of Sklyarov.

[0] https://www.zdnet.com/article/dimitry-sklyarov-enemy-or-frie...

Don't plaintiffs usually also sue to recover attorney/court fees from the defendant if they win? And that usually is granted?

Almost none of the plaintiffs would ever pay. Like this case, Nintendo is supposed to get ~5 times the amount of money they claim he made. How would he ever pay that, more so while in prison?