Can't sleep so I'll join in:
I can't sleep so I'll chime in.
Murs - Love. Why? Well, one track doesn't do this justice. The entire album of Yumiko: Curse of the Merch Girl is one story. Creating an entire album dedicated to one story is pretty ambitious if you ask me even though he got a lot to already go off of seeing as it's the soundtrack to a Comic Book.
Akala - Comedy Tragedy History Why?
''Akala was on a British radio show called BBC1 Extra, and the host challenged him to create a freestyle incorporating the titles of 27 Shakespeare plays. Akala had about 10 minutes to write the rap, and the first two verses of this song is what he came up with!
When he recorded the track in the studio, he added the next two verses which are composed of famous quotations from Shakespeare plays.''
Tonedeff - Crispy (192 BPM) Why? Idk man, rapping at 192 bpm... You tell me.
Ill Bill - My Uncle. Why? Trying to save someone from heavy addiction with a song as a last resort makes it to this list easily.
Mac Dre - Back N Da Hood Why? Haven't really looked into it but as far as I know the Back N Da Hood EP got several tracks recorded from jail and might be first(?) to do it in rap, and I think just that alone qualifies for this thread.