That is sound criteria.

That's fair. I definitely don't think it was his most ambitious song on its own, but I'd say releasing it as a single was ambitious - or at the very least a bit of a gamble. Seems less so in hindsight since it was such a massive success.

Most ambitious rap songs.... probably any diss track aimed at Eminem! ;)

"Among the Sleep" by Cage

Insane storytelling. A series of dreams.

Blackalicous - Alphabet Aerobics

Prince Paul - A Prince Among Thieves album

Very ambitious concept album

I binge listened to this for about a month when i first heard it.

Immortal technique "dance with the devil"