Top 10 unintentionally hilarious rappers:
I love rap music. Let me just get that straight before I go into this list. I think there’s something about it which can be frickin’ cool as hell when it’s done right.
However.
I think it is a hell of a challenge for a rapper to be that frickin’ cool without accidentally being hilarious. Here is a list I’ve wanted to compile for a while – the top 10 unintentionally hilarious rappers.
I’ll Deal with rappers that have been active in the past 10 years, since old school rap is a whole different level of hilarity.
10. Rick Ross
Loltastic track of choice – Every day I’m hustlin’
I remember the smile on my face when I first heard how often Rick Ross hustles. I also remember the smile when Kat Williams used the track in a comedy sketch. He’s trying so hard to be the cool drug dealer that gets the honnies, but bless him, he’s still a slightly overweight ex-correctional officer.
Though I can tell you that on my daily timetable, my daily morning routine is now called “Hustle”.
Musically, this is actually a massive beat. Brilliantly laid back Dirty South Hip Hop. Hip Hop with effectively sampled horns is always huge.
Funniest Lyric: Hmm. I may have to go with “Every day I’m Hustlin’.” Cheers for re-assuring me, I almost assumed it was weekly after you didn’t mention it 8 times after each verse.
9. Kid Rock
Loltastic track of choice - American Badass
Ah Kid Rock! Anyone who strolls on stage in a pimp suit is clearly hilarious. I’m 99% sure that he doesn’t get how funny he is.
I chose American Badass because it’s just so cool that you can’t help but crack a grin. The intro “Are you Scared” always makes me reply “Not Really”. The sheer number of hoes in bikinis around motorbikes is comedic genius.
Musically, you can’t really go wrong when you’re choosing quite possibly the most strutt-able metal riff in existence to rap over.
Funniest Lyric: so many good ones, but I’ll pick “I’m gonna F**k some hoes after I rock this place!” I wonder if he knows what subtlety means.
8. Soulja Boy
Loltastic track of choice – Soulja boy
Now, I think when gangsuh rappers pronounce things differently it’s cool. But this guy takes things to a completely different level of non-enounciation. It’s like he gets drunk to the point just before he passes out, then says whatever comes into his head.
Musically, it’s like someone took the backing track to a Nu Metal song and used it without any of the live instruments. Travis Barker proved that theory in his amazing remix. Soulja Boy – You should probably be in a band.
Funniest Lyric: “Watch me crank that roosavelt and super soak that Hoe” – …uh…what?
7. Mike Skinner
Loltastic track of choice – fit but you know it
One of the biggest british “rappers”. I use inverted commas because he is TALKING. There is a difference between rhythmic talking and rapping. If his style isn’t weird enough, he talks with a London accent… even though he’s from Birmingham. Right.
Anyway, it’s his innate britishness that makes it so funny – certain colloquialisms aren’t quite as hard hitting over a hip hop beat as others. “Clocking a grip” wins over “We’ve had a few, fair play”, for example. Plus the fact that he mentions queuing for fish and chips in a rap song. In quite a lot of detail. Brilliant.
Musically it’s indie hip hop. I absolutely hate indie music as a general rule, but some of his beats are actually catchy and danceable. Fair play, mate.
Funniest Lyric: “This night’s not even begun, yes yes oh yay” – Who needs to rhyme words that have any relevance to the topic in hand anyway?
6. Dr Dre
Loltastic track of choice - Still Dre
Now Dre has some good intentional humour and makes AMAZING beats, but he also has a tendancy to gangstuh himself up a bit. One thing gangstuhs tend to do is repeat things. A lot. For example, I never stopped assuming he was Still Dre. Thanks for re-assuring me, though.
Musically we are talking about the guy who popularised gangsta rap. Gangstuh rap. Gangster rap. However you spell it. It’s dirty, dischordant and dead cool. But also it’s so easy to parody that it’s become quite the joke. How many youtube videos are gangstuh raps of things which are normally not gangstuh? What a brilliant concept! (That’s only partly sarcastic, as I enjoy those videos)
Funniest Lyric: In the midst of a bunch of cool lines: “Barbeques every day”. He’s a straight G fo’ sho’.
5. Dizzee Rascal
Loltastic track of choice - Jus a Rascal
Wow. Actually wow. How did anyone with this accent come into existence? That “Rascal!” shout had me sewing my ass back on after laughing it off. And the one chorus where he just says “Brrap” at increasingly frequent, yet seemingly random intervals. Brilliant.
Musically it’s great, suits his flow so well – has a grime hip hop feel about it, with distorted guitar undertones. His music as a general rule is really unique… very percussive hip hop. Be sure to check out sirens too – it’s like he got KoRn to write him a beat.
Funniest Lyric: Not from this song, but “Flushing mc’s down the loo” from Fix Up Look Sharp made me burst out laughing. He is so from London that it hurts.
4. Fred Durst
Loltastic track of choice – Rollin’
I saw Limp Bizkit live at Download Festival recently and it reaffirmed why Fred Durst is an accidental comedic goldmine. The sheer number of “Limp Bizkit in the house!” and “Get the F**K Up!”s shows the extent of this rapper’s quality banter.
Fred Durst is *actually* like that. That’s what makes it funny. Plus the fact that in one of the interviews he stated he was a perfectionist. He has certainly perfected the art of telling the crowd that he and his bandmates are, in fact, on stage.
Also quite possibly the only metal band to have a dance routine for a song. It was quite an experience being there in the crowd for that.
Musically it’s quality Nu Metal. An oxymoron for some, but I frickin’ love the stuff. If Hip Hop is about power then you can’t get more powerful than chunky distorted guitar.
Funniest Lyric: “Hot Mommas, Pimp Daddies.” …Uh, Pimp Daddy, Fred?
3. 50 cent
Loltastic track of choice - 21 questions
Fiddy got this high up on the list purely on how much he boasts. Which, for a rapper, is seriously saying something. The track I Get Money always makes me laugh, not just at the intentionally funny lyrics, but the fact that 50 cent is actually that rich.
Another lol moment was in the Candy Shop video, where the chick whips off his top and he stands there looking all mean and buff. Just like in EVERY other picture of him.
Musically he’s pretty diverse. 21 Questions isn’t the best track for the beat, but things like P I M P and In da Club are classics. Gangstuh rap with a club flavour to it.
Funniest Lyric: “I love you like a fat kid love cake” – Actual genius.
2. Snoop Dogg
Loltastic track of choice - Who Am I? (What’s My Name?)
Of all the rappers I’ve heard, no-one asserts who they are more so than Snoopy D-O-double G. He must have some serious existential issues. In the track of choice the chorus has an almost choral rendition of his name that had me in stitches.
He is also one of the most unlikely looking gangstuh rappers. He looks like he could be blown over by a strong breeze.
Also, his obsession with weed tickles ones funnybone. Especially when you find out he has a weed smoking room in his mansion. Another Kat Williams reference when he mentioned smoking with snoop and they had 4 blunts being passed around. I didn’t even know what a blunt was before listening to the Doggy Dogg. What a considerate guy, educating us like that. I suppose his laid back flow comes from this, which is why his collaboration with dubstep artists “Chase and Status” worked so well.
Musically – it’s Dre, you know it’s cool gangstuh rap.
Funniest Lyric: “and up in yo bitch, is where ya might find me” != subtle. == lol.
And the Number 1 spot goes to…
1. Lil Jon
Loltastic track of choice – Real Nigga Roll Call
This man made a career out of shouting “YEAH”, “WHAT” and “OKAY!” at the top of his voice. This man created the funniest genre of rap music ever. If you ever asked me “Hey, Dave, where’s Lil Jon?” I’d be able to tell you with quite a lot of confidence that he was up in da club gettin’ crunk.
The track of choice is actually the world record for the most obscene words in a song. 295 words if you’re interested. And he released it as a single. Amazing.
You KNOW when Lil Jon is on a track. You can hear it a mile off. Listen to Usher – Yeah again and concentrate on Lil’ Jon’s backing – it’s just brilliant. For the third time in this list, Katt Williams picked up on this and got Lil Jon on stage, who promptly did his YEAH, WHAT and OKAY, then left the stage. This makes me think he might get the joke – but to be honest, anyone that can completely immerse themselves into a joke that much deserves this top spot.
Chris Rock also picked up on it. “‘Til the sweat drips from my balls” – what a lovely image to put in the chorus of your hit single.
Musically, Crunk is the funniest genre ever. You can make a crunk beat in about 3 steps.
- Make a silly, weak drum beat.
- Play a synth riff with a supersaw wave 4 times.
- Play the same riff 4 times more one octave up.
Rinse and repeat.
Funniest Lyric: YEEEEEAAAAHH!!!
So there you have it.
Do you know any more that I missed? Do you disagree with any of the choices? Share your opinion in a comment below!




This was thoroughly enjoyable. d(^_^d)
Why thank you!
LOL … Nice selection
It never really got to me that Lil Jon is all yeah and okay… Now that I concentrate on it, it’s truly hilarious… Thank you for opening my .. Umm.. Ears?
xD My pleasure. He is spectacularly one-dimensional.
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I love Dr. Dre and Snoop Dogg. I am so glad you chose Lil’ Jon as number one, that bitch is hilarious!
Needs more Lil wayne hahah
Haha he was a close number 11 xD
HAHAHAHAH u made my day xD
well me being from the bass city (miami) i think rick ross was a good choice cause ive never seen or heard of him till everyday im hustlin so i guess he isnt that big of a hustler if no one in miami has seen him around and he is not that hard to recognize…but id have to disagree with snoop and dre…lil jon is a joke as a producer and artist over all so hes a perfect number 1 lol….but hey why not teach us how to make a runners style beat..(everyday im hustlin,and most of dj khaleds beats)
lol!!! This was amazing, thanks for the compilation
I gotta say the Mike Skinner was #1 in my books hehe!
They had that on a FIFA game (If I remember correctly), it drove me up the wall… Keep up the great work man
Lmao, this is DEFINATELY missing the “Crunk Core” band brokeNCYDE. (www.myspace.com/brokencyde) Consider yourself warmed: Instead of rapping, singing, or talking, these kids scream. Fucking hilarious.
Hah, I’ve been down to support Brokencyde with my band but they pulled out of the tour =/ In any case they are hilarious. I suppose with lil’ Jon in there that’s pretty similar though
The saddest moment of my life was hearing Lil Jon mixing reqium for a dream. I nearly cried it was that bad. Its basically a slight edit of your “crunk in 3 steps”
1:
Take one of the most heart poundingly intense pieces of music written
2:
Re-do it with impressively weak synths and a poor, poor beat.
3:
YEAH! HOLD IT UP! YEAH!! WHAT? YEAH!!!
Haha love how you put this humor on the table… hystericall.. now watch me crank that roosavelt!
I think this is a okay list you made, Dave. i can do nothing but agree to the thing about tha SOULJA BOY.. dmn he suck di** when you talkin on rap… and Lil John, dmn you were right on that too.. that song is only good cuzz Ice Cube is banging it!!!
this seems like a uneducated hiphop critique list to me. snopp and dre on this list?? probably the dumbest thing ive ever heard haha. kid rock is basically a country artist now( i guess he found his genre) and i have no idea why eminem isnt on this. you could have done so much better. you farted on music with this list. amen.