All technically illegal under copyright laws unless it’s been cleared with the rights holder, usually the publisher. Almost everyone used to be able to slide under the radar because it wasn’t easy to get caught, or worth the legal cost if you did, unless it became a radio hit. If the tune was exceptionally popular it would just get released on a white label aka blank record like 2 years later.
These days with software able to scan everything uploaded everywhere in a matter of minutes it’s easy to get caught. There’s an emerging industry based on doing exactly that, and not just for sampling but mainly for piracy. Automatic DMCA threats and takedown notices get sent.
Things used to fall into the public domain more often (still took decades), but these days most people choose to extend their copyrights even well after their deaths so I doubt your grandkids will be able to use those Kanye samples.
Fair use for commentary and criticism is a real thing indeed and I have used it to my advantage, but only with video work. With music unless it’s an obvious goofy parody I don’t think there’s much chance at passing it off as a fair use case.