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

[Certain]

"B.I.B.L.E." was a Killah Priest song that was placed as a bonus track on Liquid Swords. It's a good track that does not fit sonically or lyrically with the rest of the album. Here are a few that come to mind off the top of my head:

"6 in the Morning" by Ice-T was the first openly violent gangster rap ever and clocks in at more than 7 minutes long despite telling a mostly continuous story.



"Celly" by Extended F@mm has all four members of the group telling a story via cell phone, except the reception keeps dropping.



"One Mic" by Nas features a level of dynamism rare in rap, with clear cut crescendo and decrescendo.



"One for the Griot" by J-Live tells a story with three alternate endings. And the story is told with precision and humor.



"Jackin' for Beats" by Ice Cube gave us the first example of a rapper taking popular beats and rapping over them and switching up every so often.



"The C-Quel" by Canibus is probably the only track that overlaps two different rapping vocals — and it mostly pulls it off.



And I'll nominate two full albums, both produced by Prince Paul: De La Soul's De La Soul Is Dead and Prince Paul's A Prince Among Thieves.