I don’t know about a particular song, but DMX pushed out his first two albums, both high selling and well regarded, in the span of about 6 months! That’s pretty impressive.

Edit: 1998 was a massive year for rap!

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?! 😮

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

Notorious BIG regularly switches the style of rhyming and cadence in an organized manner while freestyling. See the banrious YouTube videos that explain it.

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

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

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.

“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.

I like far too many kinds of hiphop to ever have a favorite, but here’s one that really struck me when i first heard it. The Lovely Thing Suite by Watsky. Technically multiple songs but here it is all together. I think it tells a story very powerfully.

https://youtu.be/SvlpvcqM9kQ

Here’s another artist who doesn’t get enough mentions, Spose. He’s mostly known for a song called I’m Awesome, but he never stopped making music and he has tons of great tracks. I wouldn’t say he’s the most technical rapper, but he has some of the cleverest bars out there and is really entertaining. Here 's one my favs called Greatest Shit Ever.

https://youtu.be/HSyiOMg_110

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.

3 wildly different perspectives on life lived and living life. For me its mostly the feel of the music, the lyrics.

Lacrae - Welcome to America (Before Mr glover recorded his hit)

https://m.youtube.com/watch?v=zVyEPNIR-yk

Nocando - El Camino (The big lie of the American dream)

https://m.youtube.com/watch?v=94Bxhhmm0FA

Classified - All About U (An underground Canadian hip hop wonder from the maritimes with a positive message for everyone )

https://m.youtube.com/watch?v=wuG3ZDAxLhs

Mobb Deep - Cradle to the Grave

Eminem - Role Model

Anything from Redman. Case closed

“Recently”: OG Keemo - Vorwort

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.

Story 2 - clipping.

The time signature changes create a surreal effect. In the first half of the track, it creates a feeling of being lost in thought. And then in the end it becomes a sense of panic.

If you like that, I also recommend live for no audience during a global pandemic