Monkey, Teach Me How to Freestyle Rap


Mar 28, 2001 (Updated Sep 5, 2001)


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The Bottom Line The essential guide to freestyle rapping, the monkey way.

You’d be amazed at how often kids come to me in my office or approach me when I’m spinning at a club and said, “Monkey”--or even more often, they call me “repzamza” (pronounced “re-piz-za-miz-za.)* They say, “repzamza, bestow upon me all of your infinite knowledge of freestyling.” And I say, “Kid, as much as I would love to let you in on all the secrets behind djrepulsemonkeyb’s MC skills” (except, when I say “skills,” I pronounce it with a “z”) “the subtle art of freestyle rap can only be learned by doing. You have to get on the mic and rip it up and be prepared to be booed off the stage ‘cause you ain’t no good.”

And they say, “But repzamza, couldn’t you at least give me some tips to get me started?”

And I say, “No, kid, you bug me. Get lost.”

And they say, “Please MC Monkey Dogg. Please.”

And I say, “No.”

And they say, “Pretty please with sugar on top…?”

And I say, “No.”

And then they hit me. They knock me on the ground and poke at me with sticks. They taunt me by saying, “What’s up now, Mr. DJ? Not such a hot MC now, are you? Your mic skillz don’t mean nothing. Why, you aren’t even a real monkey, you’re just some schmuck who nobody can see through the computer.”

And, as they kick me, I say, “Please stop. Please. I’m a bleeder. I bruise easily.”

And they say “Ha Ha Ha. You just should have told us the secrets to freestyle rap. Now you’ve entered a world of pain. A world of pain.”

Inevitably, I wake up bruised and winded in some dark alleyway with no clothes on and the word “Poser” written in black ink across my forehead. But I guess that’s just another typical Saturday night for the monkey.

Sometimes it’s not easy being a world-class emcee.

So, in some attempt to protect myself from future beatings, I’ve decided to post the tricks of the freestyle trade for the whole world to see. Or at least the world of epinions.


Monkey, What is freestyle rap?

I’m glad you asked. Freestyle rap is a medium of expression in which the artist attempts to create verbal poetry at the spur of the moment in the style of modern “hip hop” music. It’s an art that’s easy to begin, but takes years to perfect.

Some say freestyle rap came about when Master P began his No Limit Records label and thought he could make millions of dollars by releasing a new album every three days. Master P would pull in any old guy off the street and give them a cool rap name like “Kool G Cocaine Llama” or “Zippy Luv Nut X Squared.” He'd stick a microphone in their face and ask questions like “Why’re you the baddest mutha on the mic?” and record their answers. Then he’d attach a pre-made beat to their answer and put it down on a CD.

The most famous of Master P’s prodigy, was a young man named M-No-Lo-Spank, who thought it would be “phat” if his answers to Master P’s questions were delivered with rhyme and rhythm. Thus came the infamous battle rap:

“I get up on the mic like a gorilla on bananas/
Excuse my bad mannas/
I rhyme over burps and farts like my uncle Dan does/
Then I go to the San Diego zoo just to visit the cute, fluffy pandas/
Those pandas sure are cute you know/
I like it when they eat bamboo/
It makes me giggle”


Some say M-No-Lo-Spank was an alcoholic. Others believe he gave birth to the art of freestyle rap.

Some experts point to the origin of freestyle rap within the movie The Princess Bride.

But I maintain that I, djrepulsemonkeyb, invented freestyle rap at a young age in an attempt to fend off junior high school bullies on the playground. Often, I would be heard screaming,

“Best back up off me, or I’ll tell Principal Frazier/
My folks’ll sue the school and that’ll make him even crazier/
He’ll keep a stern eye on you and whoever else plays here/
Or at least let me buy you some gourmet beer/
Just please please please don’t cut me with your razor.


Usually, they’d leave me alone, obviously intimidated by my flow.


Monkey, How should I get started freestyling?

I’m glad you asked. I’ve found the best way to begin your career as a freestyle rapper is to inject rhyme into everyday conversation. For example, at the dinner table:

“I’m damn hungry like a leper/
Like Ini Kamozi I’m a hot stepper/
Please, mom, pass me the salt and pepper.”


Or in the grocery:

“It’s no wonder these melons are on sale/
They’re looking kind of pale/
But I’ll buy some anyway-le/
And feed them to my ignorant nephew Dale”



Here are a couple of tips which may aid you in your freestyling:

1) Don’t worry about rhythm.

Most rappers don’t.

Forgetting about pesky rhythm will only free you up to bust rhymes like:

“I’m a killa in the dark/
I make a spark like wintergreen life savers/
My buddy Dave waves to ugly pilots and/
Like those disease carrying pigeons I hang out all day in the park.”



2) Don’t worry about rhyming.

Too many rappers get all bent out of shape over making words rhyme. Don’t be one of them.


3) Don’t worry about making sense.

This is a rule that members of the Wu-Tang Clan have been following for years. One way to approach freestyle is simply to string together a list of objects or actions:

“Dirty diapers/
Set your house on fire/
Don’t get bit by vipers/
Children get hyper/
Take your Ritalin/
I like my women playing fiddle.”


Or feel free to make up words and use nonsense:

“When punks step up I be like hoo hoo hah/
Hey nonny nonny doo doo dip doo daw/
Words I spitty ditty get laid down like law/
If you got a problem, you can fee fie faw/
I don’t make any sense but I still keep it raw”



Monkey, What is THE secret to freestyle rapping?

I’m glad you asked. The secret to freestyle rap is writing your rhymes before you supposedly make them up. This way, people will think that the flow you’ve been working on for weeks just came to you off the top of your head. If you spend a great amount of time sculpting an intricate rap and then pretend to make it up as you go along, people will begin to think you’re a lyrical genius. A GENIUS, I say. Perhaps the greatest MC to emerge from whatever hood you grew up in. Perhaps the greatest freestyle rapper EVER. Next to me, that is.

Yes, kids, the only way to win is to cheat.

Thank you for reading.













*To our knowledge, the monkey does not have an office, he has never spun at a club, nor has he ever been referred to as “repzamza.” Ever.







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