What are some of the most ambitious rap songs of all time?

[Schadenfreude]

J. Cole - "Wet Dreamz"

Lupe Fiasco - "Gotta Eat"

That song Aesop Rock made about a dog drowning, I forget the name.

[timeless]

Originally Posted by Schadenfreude

J. Cole - "Wet Dreamz"

Lupe Fiasco - "Gotta Eat"

That song Aesop Rock made about a dog drowning, I forget the name.

Ruby '81. Was gonna list that.

Eyedea - birth of a fish
Mr. Lif - what about us?
Nas ft. AZ - the essence
Nas if I ruled the world
Krs one - somebody

[Schadenfreude]

Originally Posted by timeless

Ruby '81. Was gonna list that.

Word.

Even tho this thread's about SONGS, Lupe's "The Cool" & "Tetsuo & Youth" were brilliantly ambitious. Shit just listen to T&Y in reverse order.

Also Kendrick's last project "To Pimp A Butterfly" was respectfully ambitious, for offering a conscious, commercial album during the 'Ratchet Era' of pop rap.