Louis Arge
Published on

How to Freestyle Like Harry Mack

This is based on a twitter thread I wrote about Harry Mack's freestyle process.

Harry Mack is widely regarded as the best freestyle rapper of all time.

I had the opportunity to practice with him for 12 sessions over 3 months, because he was teaching freestyle rap over Zoom in the early days of his career (2020).

So... how do you get this good at freestyle rapping? Well, apart from having an IQ of 200, there are a few specific subskills you can drill which puts you far ahead. Here are some that Harry Mack taught me & some I've stumbled upon by myself:

1. Work in setup/punchline.

This is the biggest "free lunch" in freestyle rap: there's a weird effect where the punchline (the second bar in a rhyme pair) will be much more salient to the listener than the setup.

You exploit this effect by:

  1. deciding The Thing you wanna say (if the audience suggests a word, this could be it)
  2. figuring out a Setup Word, something that rhymes with The Thing
  3. then first, you do a whole bar which ends in the Setup Word
  4. then afterwards, you do a whole bar which ends in The Thing

To the listener it's magical how The Thing (often a word they picked) just happened to rhyme with the rest of your improvised verse.

The thought process is supposed to be like:

> you're freestyling for a person, with a red hat on
> you decice to rap about the "RED HAT"
> you come up with a less impressive line, which rhymes; it could end in "GET MAD"
> "when i step on stage, all these other rappers GET MAD"
> "but all the fans cheer, especially you in the RED HAT"

The person in the red hat is MIND BLOWN, that his hat simply happened to rhyme with the rest of your bars. He was not expecting that at all.

The pattern becomes:

*unimpressive* line, then *impressive* line
*unimpressive* line, then *impressive* line
*unimpressive* line, then *impressive* line
...

And luckily the human brain only pays attention to the impressive bars.

2. Do lots of rhyming drills. I'd not be surprised if Harry's spent 100s of hours practicing rhyming random dictionary words. It's wickedly memorizable, and the whole point is to minimize what you need to spend IQ-seconds on. I'd guess if you say a word, he can find rhymes at <5ms per rhyme.

The practice is really simple:

  • Go to a random word generator, like this one I made
  • Generate a word, and come up with at least 3 rhymes for it
  • If you were slow for any given word, practice it extra hard
    • Repeat the rhymes many times (💭 "slaughter, water, daughter, quarter")
    • Repeat the rhymes, in context (💭 "you gotta pay a quarter, my flow is like water")
  • Do this for a lot of words

Once rhyming is second nature, you can spend more time on every other part of the freestyle; this is the tide that lifts all boats.

3. Practice filler. Sometimes you come up with two bars, but when you rap them on the beat, they don't fit. They're too short, they don't have much rhythm, the rhymes don't line up, etc. You need to practice filler.

Let's say you came up with:

  • "You gotta pay a quarter" (setup)
  • "We're at the beach, so my flow is like water" (punchline)

You realize, that (1) the first bar is way too short, and (2) the second bar feels off by one syllable. Try to learn a bunch of ways to adjust them. For example, for the first bar:

  • "You gotta pay a quarter" -> Add prefix about how good/special/fancy you are -> "Just to get to shake my hand, you gotta pay a quarter"

And for the second bar:

  • "We're at the beach, so my flow is like water" -> Expand "we're" to "we be" -> "We be at the beach, so my flow is like water"

In this way, you've now made 2 mid bars sound very punchy and on-beat. You should practice this a ton, so you're effortless producing bars that sound good. The patterns are usually either:

  • Add half a sentence about how good you are
  • Add half a sentence about how bad other rappers are
  • Add half a sentence about what you'll do to the competition
  • Replace a few soft grammatical words for punchy, hard words, depending on context:
    • "are" -> "be"
    • "have" -> "got"
    • add "done" before verbs, "i felt" -> "i done felt"
    • "them" -> "'em"

4. Pre-compute wordplay, punchlines, etc.

With Harry Mack, you can tell he oftentimes will use similar punchlines across freestyles, when common words come up.

It's good to build out an arsenal of punchlines, so you can just recall them. When "water" comes up, you can just recall "my flow is like water". Or whatever it is.

This comes naturally from general practice with random words, but you could probably also get there faster by using spaced repetition to memorize punchlines (e.g. make an Anki deck).


One of the things I admire most about Harry, is how compartmentalized his practice of rap is.

If you go back through his catalogue, you can see him picking (1) thing at a time to "fix". It's very obvious.

One month he's working on removing some verbal ticks, the next month he's working on memorizing more "suggestion words" (back in the day he would take 1 word at a time, nowadays he does up to 10!), next month it's adlibs, month after it's melody, etc.


Thanks to Harry Mack for teaching me these things, and thanks for reading this post.