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

[uh-oh]

best hip hop song of all time?

ambitiously created a way to stunt on everyone without rhyming half the time because of the whoa adlib. "finger near a nigga asshole like whoa", possibly the greatest line ever? buckwild the most underappreciated with his biggest banger with the cleanest dopest drums. hypnotic strings.

[Vulgar]

Posting some great examples. Nice.



"Umi Says" by Mos Def

Genre bending. Not many rappers have the guts to pull something like this off!



"1-800-Suicide" by Gravediggaz

Absolute fucking legendary track. Very risky (almost offensively) concept with fun results. You can rock to this even if you've lost someone you know to a suicide (which I have)



"Addicted" by Living Legends

A song about masturbation. Very well done. Cracks me up.



"I Phantom" by Mr. Lif

He might have more ambitious thoughts than this, but the sound itself is very different. Excellent, cutting edge, and unique.



"Na Na Na" by Jae Millz

Pretty slick track.

[Eŋg]

good shit, half a dozen in the OP i thought of before reading, then read. i'll peep the ones i don't know.

liberation, da art of storytellin' pt.2, spottieottiedopalicious - outkast... most that album actually

pharoahe monch - trilogy

pos - the brave and the snake

aceyalone - the guidelines

monolith - jedi mind tricks

profits of man - killah priest (heavy mental was a dope call)

cunninlynguists - the gates

funkdoobiest - rock on

mural - lupe fiasco

the boy who cried wolf - ian kamua

four women - reflection eternal (technically nina simone)

wordsmith - chino xl

wasteland; vol.1 - CYNE

eternal sunshine/the pledge - jay elec

--that's off the top. basically just atypical shit i fuck with conceptually as much as in execution. roughly.

[Vulgar]

Exactly. thanks

[timeless]

Originally Posted by uh-oh

best hip hop song of all time?

ambitiously created a way to stunt on everyone without rhyming half the time because of the whoa adlib. "finger near a nigga asshole like whoa", possibly the greatest line ever? buckwild the most underappreciated with his biggest banger with the cleanest dopest drums. hypnotic strings.

Fuck yeah. Gta 3

[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

[Certain]

"Essaywhuman?!!!??!" by The Roots.

[Ghost1]

Speaker box/love below entire project

Surprised 3 stacks hasn't been mentioned yet tbc.

[Certain]

Every album by OutKast and Kanye West could be mentioned.

If we're including bad things, Common's Electric Circus album qualifies.

[Objective]

Love the different perspectives from characters in Apathy's tracks. School is one of them with a serious message, delivery and great use of sound effects of the like to paint a vivid image:



Eyedea - Bottle dreams, a pretty sick story about a girl that gets abused by her father. I think it's ambitious to go for a theme like that and writing a story as strong as that one because YOU CAN NOT COME WEAK on topics like that, it'd just make it creepy and weird if it did.



Cage - Agent Orange for going off a classic movie theme and pulling it off in excellent fashion.



M9, Cyrus Malachi, Chemo, Masikah - Paintbrush, added for using painting/art as a metaphor/theme for writing lyrics.



Sage Francis - Escape Artist for using magic as a metaphor for rap. From Rap Genius: ''An extended metaphor on how being an emcee is like being a magician. Sage pulled the ultimate vanishing act when he got out of the game.''

[dead man]

[oats]

ambitious is a trippy word though. I'm most impressed with unique MCing angles or lyrical acrobatics. shit like 10 Crack Commandments and Ebonics are dope and innovative, though I wouldn't call them "ambitious."

I always thought Organized Konfusion was way ahead of their time, which is ambitious

[Wise Wiggles]

Stan, Kim, my darling- em

Mos- world world water

Lab Rats - devil's train

Aesop rock - the harbor is yours

Necro - I need drugs

Mac mall - cold sweat

[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.

[Fart]

I fully endorse what @Objective said.

Plus pretty much everything on Atmos' When Life Gives You Lemons You Paint That Shit Gold. Brilliant story telling on every track

[Frank]

Nas Hip Hop is dead

[Certain]

"Stan" is a very good pick. "Guilty Conscience" also was exceedingly ambitious, particularly considering both were singles.

[oats]

even The Way I Am was pretty ambitious as a single, especially given the bling zeitgeist of radio rap at the time

[Certain]

Originally Posted by quaker oats

even The Way I Am was pretty ambitious as a single, especially given the bling zeitgeist of radio rap at the time

"The Way I Am" was so directly within the comfort zone of Eminem fans that I disagree. There were four songs on The Marshall Mathers LP that were very similar. He was not stepping out of his comfort zone at all, even if he was stepping out of the mainstream sound.