My favorite level 5 was a bug in clang that caused it to occasionally emit incorrect code when calling a vararg function. However, the bug was harmless when combined with clang's vararg function prologue. When calling a vararg function compiled with gcc, the clang bug would cause gcc's prologue to jump to a quasi-random address vaguely nearby and continue execution in the middle of some other function. That was great fun. I wrote it up here:

https://www.mikeash.com/pyblog/friday-qa-2013-06-28-anatomy-...