Not a “song” per se, but Black Thought freestyling effortlessly for like 10 minutes straight is impressive AF: https://youtu.be/prmQgSpV3fA

For context, that show asks everybody to freestyle and some refuse, some do a few bars, but nobody goes for 10 minutes, lol.

For an actual song, and you wanna talk art, Blackalicious - Attica Black. Really love the sampling and the musicality of it, there are so many layers and it’s fun to listen to. https://youtu.be/qHRxorG8ABs

NAS- One Love (Illmatic, 1994)

The song is about a street criminal writing his friend in prison. It’s actually a literary form called “Epistolary”, where the narrative is in the form of documents, usually letters.

So anyway the song is full of the street lingo, misogyny, drug use, and violence you’ve come to expect from “gangster rap”. But just underneath, it’s also sweet and affectionate. The song is vulnerable and positive about masculine and platonic affection despite the most toxic context imaginable.

A Day at the Races by Jurassic 5

It’s just got awesome rhythm, it manages to evoke the feeling of racing (awesome song for driving; awful if you’re stuck in a traffic jam). The rhymes are excellent, poetic induction at the level of Shel Silverstein’s poem Magic.

They manage to somehow capture the smooth satisfaction of dry roads and eventual traction, the pacing of the action with zero distraction just perfect samadhi doing naughty shit with haughty wit and they got me with them in the pack even though I’m stuck back in the stack of whack traffic jams that make me slam on my brakes I love the way it gets my brain going. It’s hard to drive slow to this track especially if I listen to it back to back like crack for a sober mind this is my kind of jam man fuck:

https://youtu.be/YietowKD0vo?si=a2W4Y2lEIRbunzye

Anything from Dr. Octagonecologyst by Dr Octagon (Kool Keith)

The dense intricate rhyming structure mixed with the sci-fi jazz beats and the off the wall, juvenile lyrics are really unique and creative.

Edit: NSFW obviously

Lately, I’ve had two. One in English and the other Spanish.

English - Eminem ft Joyner Lucas - Lucky You

• The speed and rhythm are unbelievable. The musicality matches the emotion so well too. It’s insane that someone can create and perform that.

Spanish - Residente - La Catedra

• Awesome rhythm that varies throughout and a ridiculously long diss track at 12 mins lol. And just to show off, the dude raps a whole lyrical set rhyming with each of the vowels starting at 6:07. Who does that?! 😮

Edit: Just for fun, here’s a song that is impressive for being so bad by someone so important to hip-hop. The backstory is that Melle Mel was one of the original founders of hip-hop and part of the first rap group inducted to the Rock and Roll Hall of Fame. A few years ago, Melle Mel started publicly attacking Eminem for being White in hip hop. Eminem mostly ignored it, even thanking Melle Mel in this Rock and Rock Hall of Fame induction speech. However, after being attacked enough time by Melle Mel, Eminem dissed him in the song Realest by making fun of Mel’s obsession with his muscular physique. Melle Mel responded by seriously producing and disseminating this song to the public. It’s hilariously bad. Melle Mel - Kickback

I’m going to go with House of Pain, Jump Around. My reason for choosing this song is probably different than what most other people choose their songs for. This one doesn’t particularly demonstrate musical talent, but the emotional response it elicits is phenomenal, or at least this was so in its time. Back in the 90’s and early 00’s the whole house party, or bar scene would lose their minds when this song came on. Everyone would stop what they were doing, and start yelling and jumping up and down to the music. It got everyone pumped up, and ready to go. I think that itself is a talent, writing songs that motivate people to move, to act, to dance, to fight, whatever, and this song did all of those things. Plus, it’s just a fun and energetic song to listen to.

Changes from 2Pac.

It’s the Black “imagine” by Lennon, philosophically, but also approaches the cognitive dissonance of what is wrong in the world from raw, honest and depressingly still accurate lyrics 30 years on. For me, this is a far braver and more interesting song than Imagine–and Imagine is a classic. It doesn’t let listeners off the hook and even calls them out as part of the problems.

Great rhythm, beautiful melody contrast and creatively selected issues addressed.

BIGGIE

• Unbelievable - wordplay
• My Downfall - the flow
• N----z Bleed - storytelling

I heard Lyrics Born - Do That There in a mix and was impressed with the flow in the verses, especially how it plays with the backing track.

I also love Chali 2na’s flow, like Chali 2na - Comin’ Thru

Akala - Fire in the Booth 1 The flow, message, content. An artist with top skills, showcasing what he can do.

Supreme NTM - Le Pouvior Just always dug this track. Resonates with me.

Tech N9ne “Speedom (WWC2)” ft. Eminem & Krizz Kaliko

Mainly because of the insane levels of cadence and speed with which they deliver the lyrics

Eyedea & Abilities always came with some of the best and most creative hip-hop. Their entire album E & A is next level with all the aspects you referenced. I love track #2, Now: https://www.youtube.com/watch?v=uZVkW-HtSgA&t=9

“3rd Reel Judy Garland” by Restiform Bodies. The whole thing is very dense, menacing, and centered around a bunch of extras waiting in casting, unusually. Very unique writing.

Immortal Technique - One

and some others from him

I’m not a huge hip hop fan but I really like Aesop Rock’s lyricism and I like the style that astronautilus has.

The first two songs that come to mind is Aesop Rock’s citronella

https://youtu.be/dQmvt9WHfqE?si=7wbb65LTg5aPUuqk

and astronautilus the river the woods.

https://youtu.be/6jg19GyxV2Y?si=BlrJpknydCca7TrR

Both worth at least a listen in my opinion