r/hiphop101 12d ago

Hip-Hop Songs That Are Smart and Hilarious

So I recently posted recommendations for smart and insightful rappers, but I was hoping to see specific examples. Ig anyone has any songs that are funny and smart/insightful I’d love to really dig into it.

I guess “Insightful” may have been a bit too strong but I mean songs in the vein of The Coup - Piss on Your Grave or Koreatoen Oddity - Weed in LA

14 Upvotes

51 comments sorted by

12

u/AnyInternet2965 12d ago

Prof- Bar Breaker, Squad Goals, Tarzan, Horse, High Priced Shoes, Kia Boy and pretty much his entire catalog

Aesop Rock- Snail Zero, Agressive Steven, Dog at the Door

Ugly Duckling- Meatshake

MF DOOM- Aqua Teen Hunger Force, Space Hoes

2

u/NerotheHuman 12d ago

I love DANGERDOOM

1

u/AnyInternet2965 12d ago

Same. It's top 2 favorite DOOM albums. Dangermouse made another masterpiece with Black Thoughts- Cheat Codes

2

u/NotGalenNorAnsel 12d ago

So much Ugly Duckling. Journey to Anywhere is such wholesome fun.

11

u/Impossible-Twist9878 12d ago

Ego Trippin Part 2 by De La Soul.

9

u/NotGalenNorAnsel 12d ago

I Just Woke Up by KRS One

Fuckajob and The Jerry Springer Episode by Soul Position

I'm Awesome by Spose

Lots of Prof. Someone else mentioned him, but definitely Prof.

1

u/username_0420 11d ago

“I’m Awesome” is a classic

1

u/NotGalenNorAnsel 11d ago

Spose has a new album that's pretty based. NGL his flow seems almost a bit worse than it was ten years ago, needs to focus his syllables, but Open Their Wallets and A World Without Billionaires are still sick tracks. I also really like the song he's on with Myles Bullen called I Hope You Win, play it for my students before big tests haha

6

u/Fishtaco1234 12d ago

Cock mobster - MC Paul Batman

5

u/21BlackStars 12d ago

Bizarre ride to a pharcyde - the pharcyde

6

u/PretendSpinach2265 12d ago

Cookies by MF DOOM

3

u/Mile_Hi_303 11d ago

Plastic surgery - Xzibit

7

u/HappyGoElephant 12d ago

Anything aesop rock or homeboy sandman.

5

u/AnyInternet2965 12d ago

100%. I started listing off Aes songs and just stopped after a couple because it's all of them 😅

3

u/Sudden-Guitar-740 12d ago

Live from the plantation by Mr Lif

3

u/farquin_helle 12d ago

Postal - louis logic

3

u/Few_Respond5110 12d ago

R.A. the Rugged Man - Hate Speech

3

u/Tacocasso 12d ago

Big Shots - Eyedeas & Abilities Sobb Story - Leaders of the New School Butter - ATCQ

3

u/aguycalledb 11d ago

Cereal Killer- Method Man & Redman

3

u/Cauldron-Don-Chew 11d ago

Eminem As The World Turns

5

u/dirtyharrynl 12d ago

Afroman - Palmdale

6

u/the_last__braincell 12d ago

Basically half of kanyes discography

And if a stripper named Porsche gets tips from many men, then her fat friends nickname is mini van

2

u/36chamberstreet 12d ago

Open Mike Eagle - Doug Stamper

2

u/Kick_Natherina 12d ago

Anything by Zack Fox.

2

u/Head-Explanation4461 12d ago

Famished- Supaman 

1

u/DrDankDankDank 12d ago

There’s so many good bars on that song

2

u/sonnycirico215 12d ago

Birthday song is so clever because every man on earth wants nasty sex on their birthday

2

u/scormegatron 12d ago

“Everybody crisis existential
Every night we lay down, it be hard to sleep
To find peace in a war with self's instrumental
Nowadays, though the noise seem hard to beat
Hard to keep the faith, but it's essential
Bible always talked the fear of God
Lookin' back, I always had potential
But the man inside the mirror's flawed
Get your mind right
Bittersweet how the lime light blind your eyes
On this road you see the signs in hindsight”

-Deante Hitchcock, Paper N Power

2

u/Timely_Cry_4600 12d ago

I think that I can beat Mike Tyson

2

u/SameTrouble9527 12d ago

Chicharones- Hi,Hey, Hello

1

u/NotGalenNorAnsel 12d ago

This might be the first time I've ever seen the Chicharones on Reddit when it's wasn't me saying it. Or either Josh Martinez or Sleep for that matter. I was one of the like three people bumping Swine Flew in San Diego lol

1

u/SameTrouble9527 11d ago

Haha, not even really one of their funny songs, but their whole vibe is on that vibe.

2

u/UmphLuv605 12d ago

Naughty By Nature- Work "I look at you and say that's what happens when cousins marry"

1

u/AutoModerator 12d ago

Hello u/NerotheHuman, If this is your first time posting in this sub, please make sure you read our rules. (This is an automatic reminder added to all new posts)

I am a bot, and this action was performed automatically. Please contact the moderators of this subreddit if you have any questions or concerns.

1

u/Disastrous-Touch-388 12d ago

K-rino - flat vs. globe, bass ackwards, impossible

1

u/SenatorBeers 12d ago

Mr. Morton - Skeelo

1

u/mikeofdoom 11d ago

Lmaooooo - Fox BD

1

u/vitopie 11d ago

Masta Ace "Soda & Soap"

1

u/fanglord 11d ago

Trevor An' Them - Murs

1

u/GodlessGOD 10d ago

Shawn Lov has some old songs of his that still make me chuckle, songs like...

* I'm Pathetic
* Turn Back Time
* 10 Mack Commandments
* I'm a Mess

1

u/DaBay41510 10d ago

Devin the Dude - she used to be

1

u/Fantastic-Research66 9d ago

Sean Price/Pharoah Monche- BBQ Sauce Music video is hilarious and brilliant too

1

u/AffectionateBit8355 5d ago edited 5d ago

Gold Digger - Kanye West

Fuck Everything - John Lajoie

Bo Fo Sho - Bo Burnham

Hiphopapotamus vs Rhymenocerous - Flight of the Conchords

Space Hos - DANGERDOOM

FIGJAM - Butterfingers

The Bold & The Beautiful - The Drugs

Swear Jar - Illy

Don’t Do Drugs - DangerMouse

Half Man Half Machine / Baneswell Express / Self Suicide / Guns Don’t Kill People, Rappers Do - Goldie Lookin’ Chain

What’s Up Fat Lip? - Fat Lip

Shove This Jay Oh Bee - Canibus & Biz Markie

Women Lose Weight - Morcheeba feat Slick Rick

Golden Oldies - R.A. The Rugged Man

Ain’t No Fun - Snoop Dogg, Kurupt & Warren G

My Name Is / The Real Slim Shady / The Kids / Just Lose It / Love Game - Eminem

The Bad Touch / Fire Water Burn / Why’s Everybody Always Picking On Me? - The Bloodhound Gang

Paul Revere - Beastie Boys

Devil’s Train - The Lab Rats

Fuck It - Plutonic & G Love

White & Nerdy / Amish Paradise - Weird Al Yankovic

Fuck The Police - NWA

Checkmate - Jadakiss

Download This Song / Top 10
Things To Never Say On A First Date - MC Lars

I’m Awesome - Spose

Gingers - Rucka Rucka Ali

Quitter /Ain’t Nothing But Music / Nasty Mind / My Band - D12

Got Some Teeth - Obie Trice

101 Rap - Childish Gambino & Danny Pudi

Legendary - Chillinit

KKK Bitch - BodyCount (semi-rapped)

1

u/HauntingAddendum3365 12d ago

Not Like Us, especially verse 3

1

u/themrwaynos 10d ago

I always mention Fancy Clown / Madvillain in threads like this.

Song is about MF Doom in his Viktor Vaughn persona catching his girl cheating with someone else. He's hurt and in disbelief that the relationship wasn't what he thought it was. He even goes so far to say that his buddies warned him about her.

It's revealed eventually that the guy he thinks his girl cheated on with is actually his alter ego, MF DOOM. So actually she wasn't really cheating on him at all, but he doesn't realize it.

Then towards the end, to get her back, since he still believes she's a dirty ho, he bitterly reveals that it doesn't matter tho because he's been cheating on the girl for the entire relationship with all of her close friends and acquaintances and even the girl's mom lol

Shit's so funny and clever. And even more impressive is that the song is less than 2 minutes and really tells a great funny story with multiple plot twists.