What a Bunch of Freestyle Rappers Can Teach Us About Building a Better World
NYC’s Legendary Cyphers, Where Hip Hop’s Spirit of Innovation and Unity Comes Alive
Every Friday night from May through November, between the hours of 8 p.m. and midnight, an area just steps away from the Union Square subway station in New York City transforms into something extraordinary.
Amid the buzz of the city, a gathering of people emerges. It starts small but inevitably grows so dense that the crowd has to be asked (repeatedly) to step back and make room.
Instrumental Hip Hop music drifts from the center. You hear rapping, but not the performing of songs – the rapping here is freestyled, made up on-the-spot. Multiple voices switch off as participants take turns projecting their verbalizations — there is no actual microphone.
The crowd gets involved, erupting in occasional oohs and ahhs, joining in a chorus or a transitional chant. Passersby stop, look, and listen. They pull out their phones. Filming. Nodding. Smiling. It’s as if all the positive, expressive, unifying energy the city has to offer has been channeled into this one circular sliver of space, a Hip Hop happening that catches the attention of thousands of people from all walks of life, providing a brief bars-filled respite from an otherwise barbaric world.
This, my friends, is Legendary Cyphers, and in addition to that blessed respite, this display of artistic and cultural brilliance provides us a glimpse of what real unity looks like. It’s guidance that only Hip Hop can deliver.
Legendary Cyphers is not an officially sanctioned NYC event. No, it’s not illegal, but there are no permits. No ticket booths. No corporate sponsors. It’s just a New York City kinda thing, a free, open-air gathering that brings together rappers, onlookers, tourists, instrumentalists, poets, singers, and sometimes even a celebrity or two. Rubberneckers watch curiously, but many quickly submit to its gravitational pull. They soon realize that one doesn’t just watch a cypher. Even by watching, you’re IN the cypher. And, as many of the hundreds who stop by on any given Friday quickly understand, there is something almost magical about being immersed in Hip Hop in its most raw, authentic, and beautiful form.
To those less familiar, a cypher in this context represents a circle – a living, breathing symbol of equity and exchange. In Hip Hop, it’s where artists take turns from collectively holding the space to stepping into the middle to share something of themselves. Their skills. Their stories. Sometimes a bit of their soul.
There are no written rules to this time-honored tradition. Everyone simply… understands. The rhythm. The cadence. When to step in. When to step back. When to hype someone else up. In reality, it’s a masterclass in social and emotional intelligence, a spontaneous choreography of mutual respect, each moment representing vulnerability and power, competitiveness and collaboration, as well as peace, unity, love and having fun — all at once, together.
Toni Blackman, author of “Wisdom of the Cypher,” recently put it well on an Instagram post, stating:
“The Cypher is more than a circle—it’s a learning lab. In the Cypher, we grow faster because we grow together. Your win teaches me. My mistake teaches you. It’s a cliche but iron sharpens iron - we sharpen each other, challenge each other, and rise - each bar uplifts, lesson by lesson.”
It’s a lesson that can be — and is being — applied to countless fields and disciplines far removed from this chunk of concrete in lower Manhattan.
Legendary Cyphers, founded by the late Daniel "Majesty" Sanchez, is more than just a space for rappers and other artists to flex their verbal muscles. At its core, it’s a brilliant embodiment of Hip Hop's true spirit. It makes sense that it would have emerged from the mind of Majesty, who I knew and would speak with periodically when he was alive. In fact, I continue to speak about Majesty often — in my keynote talks and in the introduction of my book — as being the personification of what Hip Hop can be at its highest level.
Maj was an artist, organizer, activist, and international connector who not only rapped about injustice but walked the walk with revolutionary strides. Whether it was locking arms with protestors in New York or coordinating solidarity events, Majesty lived the values of Hip Hop as a force for societal innovation and human upliftment.
Since his passing, a core group of artist-organizers continues to uphold the Legendary Cyphers tradition, ensuring the sacred rules of that cypher are being respected and that Majesty’s vision lives on. In this way, the event series serves yet another purpose, a sort of living personal tribute, while still serving as a beacon of those ideals, a light guiding those who are fueled and inspired by the true tenets of Hip Hop culture into this sacred sanctuary.
What stands out to many is just how organic it all is, from its only-supposed-to-have-been-a-one-off inception to its ongoing execution. There are no velvet ropes or gatekeepers here. Just as it has been throughout Hip Hop history, anyone can step into the cypher, regardless of ethnicity, age, gender, background, or skill level — as long as they step with respect. One doesn’t have to be a master lyricist. One just needs to honor the space. Novice? This community will cheer you on. Nervous? This community will hold you up. Just an observer? You’re just as important.
No matter who you are, you have a place here.
In fact, I am frequently on record saying that an authentic Hip Hop cypher is one of the purest examples of inclusivity there is, and Legendary Cyphers is a place that the world can see it in action. On any given night you might see a kid from Queens or a backpacker from France dropping bars. A woman with a guitar might slide into the middle and change the mood entirely. A singer might jump in and blow the proverbial roof off. There will almost certainly be an impromptu back and forth between rappers that a causal listener might swear was rehearsed, but definitely wasn’t.
This is Hip Hop as spectacle in the best sense of the word, one of several Wonders of the Hip Hop World that provides entertainment through communion, welcomes collaboration, and offers up space for catharsis.
Mind you, Union Square is one of the busiest, most diverse intersections in New York City. It’s a living, breathing, swirling cross-section of the world. That this space can transform into something so unified and intentional, without a stage or a spotlight or Live Nation involved, speaks volumes about what Hip Hop is truly capable of and highlights the characteristics that exist in its DNA that equal way more than the sum of its parts.
We are talking about more than a form of expression, and certainly more than just music. To understand Legendary Cyphers is to understand leadership and community building. It’s one of many reasons why only by truly understanding Hip Hop can we understand what true innovation is.
In a world that so often wants to commodify, categorize, or criticize Hip Hop, Legendary Cyphers defiantly stands as a compelling counterforce to the narrow, often racially biased and/or culturally ignorant perceptions that dominate mainstream media and the genpop zeitgiest: the idea that Hip Hop is to only be defined by its most commercially or controversially visible aspects. Those less familiar with the culture have no idea that at 9:47 PM on a random summer Friday, there's a kid from rural Ohio, a tourist from Sweden, and a business executive from Brooklyn all nodding their heads in unison as someone spits something brilliant, off the dome, in the middle of Union Square Park.
There’s something really powerful about that.
For Hip Hop heads jaded by the overly capitalistic trajectory of their beloved culture, this isn’t nostalgia! This is happening right now. In 2025. Hip Hop never stopped being brilliant or fun or subversive or counterculture. It does not represent the downfall of the youth. It is not anti-Black.
Legendary Cyphers is proof, and in this regard, represents a microcosm of how it is indeed possible to uplift marginalized voices, unify people across differences, create dialogue, celebrate expression, and model a new kind of collaborative democracy. In a time of deep social division and political polarization, the cypher is a reminder that despite what we see every day, it still remains within our ability to listen, to uplift, and to build things together.
Let me be clear: not everyone in the cypher agrees on politics or policy and mere association with Hip Hop doesn’t mean one is exempt from being problematic. But it’s a little different in the cypher. One thing every participant and onlooker agrees on is the moment. On the circle. On the energy that binds them in that space. And in that unity, even if fleeting and only on the surface, lives a spark of possibility. It’s a reminder that a different world is not only possible, it’s already happening in small, powerful ways. Right in front of our eyes. And ears.
We need to not overlook these moments. We need to build on them.
In fact, this is pretty much the throughline in my book, Hip Hop Can Save America! Inspiration for the Nation from a Culture of Innovation. Legendary Cyphers isn’t just a cool, fun Friday night event – though it is that, for sure. The phenomenon sits at the center of a much larger movement, one I expand upon in the book, as I explore how Hip Hop has grown far beyond its musical roots and now fuels innovation in education, health and mental wellness, civic engagement, the arts, and more. The book was written to implore everyone to truly look at what this culture offers: valuable guidance and viable strategies for approaching real-world problems in completely new ways that must include and benefit the participants who birthed and nurtured this vast and vibrant culture in the first place — but that can also include and benefit us all.
One example stands front and center on Friday nights during summers in New York City summer. Others exist, if we know how to recognize them.
If you ask me, Legendary Cyphers is sacred ground. I’ve mentioned it in nearly every keynote I’ve ever given. It’s on the itinerary for my upcoming NYC trip with the world famous #BabyGirlFaces. Of the dozens of touristy things we’d like to do, this one is non-negotiable. If my father — a distinguished sociology professor who studied cultures around the world — were alive today, I’d unquestionably have brought him, and he would have loved it. Mrs. Faces has gone with me. I've seen old friends from the indie NY Hip Hop scene there. I’ve met strangers there that I still communicate with. No matter how long I stay there – five minutes or hours – I always leave inspired.
It’s not just something to witness. It’s something to feel. To absorb. To be changed by. To learn from.
It’s part of a vast, living blueprint for what Hip Hop has always been and for what society could still be, if enough of us really want it to be. But we all need to learn how to look toward Hip Hop for inspiration and innovation, not just entertainment. If we do, the results could be…
Legendary.
There are so many more inspiring lessons to be learned from Legendary Cyphers, the Hip Hop cypher itself, and Hip Hop culture as a whole – lessons that can provide us guidance when it comes to developing new and truly innovative ways to approach problem solving in today’s society.
If this essay resonated with you, I invite you to stick around. This is just one story within a much larger movement and I’ll continue sharing real-world examples and new insights as to how Hip Hop’s principles of creativity, resilience, and collaboration can help us remix the way we educate, lead, build community, and change broken and oppressive systems for good.
Please check the resources below, and join the HHCSA community. Let’s rethink what’s possible, and remix the world for the better, together.
For more specialized information or to discuss booking me as a speaker or consultant, just reply to this newsletter, click the button below, email me at info@mannyfaces.com, or visit www.mannyfaces.com
MORE FROM THE WORLD’S MOST ENLIGHTENING HIP HOP MEDIA ECOSYSTEM:
📖 BUY THE BOOK ➡️ “Hip Hop Can Save America! Inspiration for the Nation from a Culture of Innovation”
🎧 “Hip Hop Can Save America!” Podcast
📺 “Hip Hop Can Save America!” Livestreams / Videos
🫂 “Hip Hop Can Save America!” Discord Community
💬 “Hip Hop Can Save America!” Subreddit
✌️