Song: "Suicidal Thoughts" (1994)
Album: Ready to Die

Of course "Suicidal Thoughts" is about suicidal guilt. You can get that from the title. But the realization that's key here—the one that pulls you into the dark, seemingly endless vortex at the center of this song from its first moments—is the one that takes place when all the rationalizations for suicide are stripped away, and naked self-hatred ("I'm a piece of shit") takes hold. It's as bleak as rap music gets, and also, as perfect as that bleakness gets, too.