10 Times Harry Mack Took Freestyling to Another Level Hip-hop's most underrated lyricist is easy to find, even if you can't see him yet.

Harry Mack is the best rapper on the mic, and I don’t say that lightly.

If you know the name, you already know I’m right (and I hope you get a kick out of how often I use Harry Mack instead of shortening his name to Mack in this blog), but for the sake of hip-hop, let’s dive into why that is.

Harry Mack is an underrated MC and beatmaker who you can find freestyling every Wednesday night on YouTube. I’ve been catching him since November, and I promise you won’t be disappointed in his skills. But don’t just take my word for it – Harry Mack is also your favorite rapper’s favorite rapper. He comes with the cosign from some of the biggest names in hip-hop, thanks to Power 106 FM for showing him love.

Here’s Kendrick Lamar telling Mack on live radio that his freestyling skills inspire him back in 2017.

Joey Bada$$ left the room just as impressed.

The man is a lyrical genius, and he doesn’t get enough recognition for his talent. If you’re not already rocking with Harry Mack, I’m about to drop 10 good reasons why. To do so, we’re going to zero in on his live performances.

But we’ll ignore his freestyles on shows like Ellen. It’s ok, but it’s not the cream of his crop.

Harry Mack has a YouTube series where he roams the streets of California freestyling to people. He asks you to throw out words, and he’ll start going. Because he’s a clean-cut caucasian and comes across so polite, people think they’re going to hear some corny white dude rapping. The next thing you know, he’s taking them on a journey.

Anytime people talk, he incorporates it into the rhyme, and his personality shines. What strikes me most about watching Mack on the mic is he’s always having fun. You can see that this is his true passion.

But it’s not just that he thinks fast – Harry Mack has bars. He has punchlines, and he creates some of the coolest hip-hop moments you’ll ever see. Without further ado, here are the top 10 Harry Mack moments rapping in L.A.

I apologize in advance if the timecodes don’t transfer. I’ll call them out in the blog so you know where to watch.

10. Harry Mack Calls Out the Water Bottle in the Bag

We’re gonna start with one of Mack’s favorite things to rhyme about – water bottles. Walking around, it can be difficult to come up with things to throw into the rhyme. You can see his gameplan by binging these – clothes are where he gets warmed up, and water bottles are where he hits the throttle.

We’ll get to more of these moments in a minute, but for a quick smile, check out at 8:42 when he gets the Asian guy on the bench into it then hits him with the reference to the Nalgene water bottle in his bag. The guy appropriately loses his shit, as did I while watching on my couch. Harry Mack feeds off the energy, and this is a good intro to his brilliance.

9. Harry Mack Pays His Respects to Kobe Bryant

Harry Mack loves basketball, and when he spits about the sport, he’s on fire like NBA Jams. If you live in L.A., he’s the dude who spit that fire Kobe Bryant Freestyle on Real 92.3’s The Cruz Show after his death. I was bumping Lil Wayne’s Kobe Bryant until I came across this insane freestyle dedication to Kobe, with lines like:

“Seems like the type of dude who works with persistence so when he gets the ball on the court, he can wish it into existence. ”

It’s already one of the strongest freestyles of 2020, kicking it off hard.

8. Harry Mack Raps About Condiments and Funky Slaps

Harry Mack goes hard on condiments when given the word mayonaise at 4:45. He hits up both pronounciations and does some crazy mustard and ketchup puns, winning the crowd over. Soon he has two of them throwing out the words “slap” and “funk,” and he destroys the beat and gets into his zone.

Two sessions later, he goes in on a dude eating a burrito for lunch. He describes everything going on, hits the orange rhyme, and makes me want a burrito. I’m hungry, thanks to Harry Mack.

7. Harry Mack Gives a Woman a Genuine Smile at Sunset

In his second episode of Guerilla Bars, Mack starts at the Melrose Trading Post before moving to the Griffith Observatory for sunset. He’s not sure how his rapping is going to go over, and at one point the security guard does even approach him. Unfazed, he keeps going, and soon magic happens.

At 15:26, he passes a warning from security on to one of his listeners (presumably something she tells him off camera). Then he starts walking toward the parking lot and rapping. At this point, a woman moves toward the ledge for her photographer. He points it out, she smiles, then he goes back and says “you’re welcome – I just gave you a genuine smile.” – it’s genius.

6. Harry Mack Ciphers Get You Higher Than Weed

Being in California, it’s inevitable that people continuously ask Harry Mack to rhyme about weed. He does so with precision every time. In fact, this video starts with him making the reference (and he drops the reference with the muscle guys on the beach), but it’s when he starts a cipher with the MMD dispensary agents that he takes off. These guys know what they’re doing and they help him make it fun.

He falls just short of battling (people are constantly asking him to battle, and he occassionally does it, even if he keeps it off camera) PCBabyy. These guys are a trip to watch show of their L.A. cannabis shine. Guerilla Bars 3 is also where he starts to really figure out how to control and gather crowds while he’s out in public. Like he says, he knew if he got the bride, they would make some noise.

5. No Seriously…Harry Mack Lyrics Are Harder Than Weed

In his Santa Monica freestyle, Harry Mack shows off a great range in front of a great crowd. At 5:37, someone throws out weed again, and suddenly Harry Mack sounds more like Ice Cube while putting in 16 bars on weed. It’s a dope freestyle that quickly gets back into the crowd.

4. Harry Mack Raps About Robotoids and Donald Trump

Everyone thinks they’re going easy on Harry Mack in public, because they don’t know who he is. Live crowds are basically looking around at the same stuff he is, so it’s easier for him to get on the same wavelength. He spent years with his friends challenging him before he came out into public with his skills. His fans are brutal. When you tune into Wordplay Wednesday, people really try throwing him off, and there’s a woman who does this at 2:18 with robotoid.

Once Mack figures out what it is, he goes in on A.I. and really rewards her for the challenge. Then at 12:45, after being rejected by someone, he gets a request from a woman to rhyme about “Donald Trump and his lying ass.” His voice sounds like Notorious B.I.G., so the OG woman from Jamaica, Queens, New York is thoroughly impressed with how he handles her request.

3. Harry Mack Freestyles Like Twista Longer than Twista

In 2017, Mack was still a badass rapper, but he wasn’t sure how to make the best use of his talents. He and his friend Nolan go to Venice and see if they can grab a crowd. Any musician who ever played on the street knows there are some great places to do this, but it’s not always easy to make magic happen. Harry Mack’s street cred jumps as soon as Twista’s Overnight Celebrity beat starts at 2:25.

There’s already a dozen people surrounding him when he digs in and speed raps a flawless freestyle. Everyone around him is smiling and giggling with him. The crowd soon triples, and he even gets them to raise a hand in the air. By the end, he has another crowd wanting a performance and he stays humble while blowing their minds.

2. Harry Mack Brings Down the Rose Bowl Flea Market

Harry Mack gets in his zone on this original beat of his in late October 2019 at the Rose Bowl Flea Market. While this entire video is fire, the best part comes at 4:11. Mack catches a group of four women who were not initially going to let him go. In a blow-off fashion, he’s given the word pussy to start, and he dives right on in to start speed-punching that g-spot.

He calls the girl out for saying pussy with the cross tattoo, two of them get into it, while the other two try to stay out of his peripheral. When he hits his “sweet Jesus, when I kick the freestyle, man they can’t believe it. He’s just too fresh when he does what he does,” it’s clear to this group they just tried sleeping on a lyrical God, and he rubs it in continuously. I’ve had this part of this freestyle on a 10x loop since seeing it. The group before those women got a great performance, but this one is epic and must be documented for the sake of hip-hop.

1. Harry Mack Troubleshoots Instagram Profile While Rapping

Harry Mack does a lot of crazy things in his lyrics. He set a new level in the second group, starting at 2:40, but it’s at 4:12 where he launches himself straight into space. The guy in the Olympics jacket starts filming him freestyling then asks for his Instagram account. He’s unfortunately typing “Henry Mack,” and he can’t find him.

Mid-line, Mack teaches him how to spell his name and find him on Instagram. He then realizes he has a chance to poster dunk and seizes it, going 16 more bars in on about how great of a freestyler he is. It’s like watching a Hollywood musical play out, and belongs in a TV show or movie. I’m curious to see if Lil Dicky’s FX show Dave can hold even a candle to Guerilla Bars from Harrry Mack.

As much as Lil Dicky talks about getting play, the blonde at the beginning of this took the hair tie off her finger when he called it a ring. The previous ones were fanning themselves off. Harry Mack gets panties wet.

It’s like that y’all!


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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