With a culture steeped in hubris and violence, Hip-Hop is arguably music’s most humorless genre. Rap’s ain’t nothing nice-attitude fostered a culture ripe for parody; nowadays every major single release will be followed by some shitty YouTube spoof (or a hot white girl playing an acoustic cover). In fact, yours truly got started in the comedy game doing just that. While most attempts to simultaneously spit a rhyme and crack a joke fall flat, here is a list of the 7 Funniest Rap Songs of All Time.
7. “Amish Paradise”- “Weird Al” Yankovic
The OG and gold standard of lulz-worthy rhymes. Weird Al flipped Coolio’s somber street life tale into a silly romp about Mennonite life. While the original was a one-hit wonder (Unless you count the Kenan & Kel theme), The Weird One’s spoofs have been chart-toppers for nearly 30 years. Nothing funny about that.
6. “Crazy Rap”- Afroman
If I ever become the leader of a secret society bent on world domination, knowing all the words to Colt 45 would definitely be the final step in initiating new members. People act like “Because I Got High” was Afroman’s best song. Not me, I celebrate his entire catalogue.
5. “Ho”- Ludacris
A summer camp bunk favorite and the first song on our list by a legitimate rapper. Luda has always been a versatile artist and his sense of humor is ever-present in his rhymes. As is his love of loose ladies. Luda’s known for his hits like “Ho” “Hoes in Different Area Codes” “ Hoe, Hoe, Hoe, Your Boat”. The man likes to fuck sluts, people!
4. “Beef Wit Us”- ItsTheReal
The Brothers Rosenthal have been in the hip-hop comedy game for a minute, poking fun at the culture through their popular ItsTheReal web sketches since 2007. Just last week they dropped their debut mixtape, “Urbane Outfitters” replete with hip-hop heavyweights including this ode to shit-talking feat. Maino. As for the song’s outro, we have an instant quotable:
“When I said, ‘You put the 'bitch' in 'obituary,'’ I totally didn't mean that. It was taken out of context.”
3. “Without Me”- Eminem
Eminem is one of the greatest rappers of all time. He’s also as funny as he is lyrical. Em’s album cuts are chock full of morbid humor, but it’s his light-hearted singles that always get the most laughs. Whether he’s skewering the latest pop music icon or lambasting society as a whole, nobody blends skill and silliness quite like Slim Shady. Honorable mention goes to D12, Bizarre still haunts my dreams.
2. “Mope”-Bloodhound Gang
I know this one is probably unknown to most of you, but Bloodhound Gang is tremendously underrated as comedy rappers. Jimmy Pop’s lyrics are full of clever puns, double entendres, and crazy cultural references. I know you’re reading this from the desk of your accounting internship, but when you can, give this song a good listen. To Bloodhound Gang, I’m giving props like Gallagher.
1. “I’m On A Boat”- The Lonely Island
Andy, Jorma, and Akiva are the current kings of comedy rap, and for good reason. This song has it all- ripping on hip-hop’s materialistic culture, a collaboration with a major star, a fucking mermaid! I could go on all day. Perhaps what’s best about “I’m On A Boat” is that it’s simultaneously hilarious and infectious. How many songs can have people laughing and dancing at the same time? 13? Fine, but that’s like 13 out of one vagillion. This entire list could be Lonely Island hits, but we had to apply the mercy rule.
Did I get these comedy cuts right? Think I missed one? You’re wrong, because I though about that song and just didn’t think it broke the top 7. Either way, Share your picks and war stories in the Comments Section!
Krum is an NYC based comedian. Follow him on Twitter @KrumLifeDotCom.