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They did, eventually. The first PlayStation was relatively easy to pirate for (with a mod chip), but it took a while for that stuff to become available. Someone had to go and manufacture the chips, or reverse engineer the check.
By the time that scene matured, Sega released the Dreamcast right into a more sophisticated piracy scene that could apply lessons learned to the Dreamcast right away.
On paper, Sega had more sophisticated copy protection than the first PlayStation did. But it also released 4 years later.
Self deprecation comes off wrong when it seems like the thing you’re criticizing is actually important, and that you actually believe it.
So it’s funny when the audience knows you don’t believe it’s important, either because everyone agrees it’s not important (“I can’t sing on tune to save my life”) or if it’s a particular example that doesn’t matter (“I’m such a bad mom because [something inconsequential]),” or if it’s a topic that people can see isn’t important to you (jokes about being socially awkward, bad at your job, etc.).
If you’re in one of those lanes, you can go pretty hard on yourself before it seems to go too far.