Everyone did it. If you went to middle school anytime between 1980 and today, you probably spent a math class or two sketching that weird, interlocking "S" on the back of your notebook. You know the one—six vertical lines, a few diagonal strokes, and suddenly you have a geometric masterpiece. People call it the "Gangster S," the "Superman S," or even the "Stüssy S," though honestly, none of those names are technically right.
It’s a piece of universal folk art. It’s the graffiti equivalent of a campfire story. It exists everywhere and nowhere at once, passed down from older siblings to younger ones like a secret handshake.
If you’re trying to figure out how to draw a gangster S perfectly, you’ve probably realized it's less about artistic talent and more about understanding a specific grid. It’s basically math. Sharp, aggressive math.
The Real Origin of the S: Myths vs. Reality
Let's clear the air first. Most people think they know where this thing came from, but they’re usually wrong.
A common theory is that it belongs to the brand Stüssy. It doesn't. Emmy-winning journalist Jon Naar, who documented the early NYC graffiti scene in The Faith of Graffiti (1974), never saw it in the early 70s tags. When Vice interviewed the team at Stüssy a few years back, they confirmed they never used it as an official logo.
Some people swear it’s a Superman logo. But the Man of Steel’s emblem is a rounded "S" inside a shield, not a blocky, pointed figure-eight. Others think it’s a gang symbol. While some groups have adopted it over the years because it looks "hard," it didn't originate with any specific set.
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Researchers like Julian Morgans have tracked the symbol as far back as the late 19th century in geometry textbooks. It’s a "baseless" icon. It belongs to the streets. It belongs to everyone.
The Step-by-Step Anatomy of the Gangster S
Stop overthinking it. Seriously. To master how to draw a gangster S, you just need to follow the 3-3 grid.
Start with six vertical lines. Draw three on top and three on the bottom. Make sure they’re roughly the same length and perfectly aligned. This is your foundation. If these are crooked, the whole thing falls apart.
Now for the diagonals. This is where the magic happens. Connect the bottom of the first top line to the top of the second bottom line. Then, connect the bottom of the second top line to the top of the third bottom line. You’re basically weaving them together.
Next, cap the ends. Draw a "V" shape at the very top to connect the first and third lines. Do the same thing—an upside-down "V"—at the bottom. Finally, close off the middle gaps with two small diagonal lines that point inward.
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Boom. You’ve just created a piece of cultural history.
Why This Specific Shape Sticks in Our Brains
There’s a reason we don't draw a "Gangster B" or a "Gangster T."
The "S" is symmetrical. Sorta. It has what mathematicians call rotational symmetry. If you flip it upside down, it looks exactly the same. That’s satisfying for the human brain. We love patterns. We love things that fit together like a puzzle.
It feels aggressive because of the sharp angles. In the world of typography and street art, sharp points convey a different energy than rounded curves. It looks like it was carved with a blade or spray-painted in a hurry. That "edgy" vibe is exactly why kids in suburban detention halls and urban street artists alike have gravitated toward it for decades.
Beyond the Basic Pencil Sketch
Once you’ve got the basic shape down, you can start messing with it. This is where you move from "bored student" to "actual artist."
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- 3D Effects: Most people add a "shadow" to one side. If you draw small lines extending at a 45-degree angle from every corner and connect them, the S pops off the page.
- The Chrome Look: This was big in the 90s. You shade the bottom half dark and leave the top half light, creating a horizon line in the middle. It makes the letter look like it’s made of polished metal.
- Melting S: If you want to get really "street," draw drips coming off the bottom points. It makes it look like fresh paint is sliding down a brick wall.
Common Mistakes Beginners Make
Don't crowd the lines. If the six vertical lines are too close together, the diagonals will look like a jumbled mess. Give them breathing room.
Also, watch your angles. The "V" caps at the top and bottom need to be sharp. If they’re too flat, the S looks squashed. If they’re too tall, it looks like a weird skyscraper.
Actually, the biggest mistake is trying to make it too perfect. The beauty of the gangster S is its grit. It’s meant to be drawn on a desk, a bathroom stall, or a dusty window. It’s a symbol of "I was here."
Practical Next Steps for the Aspiring Artist
Learning how to draw a gangster S is just the entry point into a much wider world of lettering and typography. It teaches you about grids, spacing, and the power of simple geometric shapes.
- Grab a piece of graph paper. It makes the six-line setup much easier to practice until you have the muscle memory to do it on blank paper.
- Experiment with "Wildstyle" variations. Try stretching the points or adding "arrows" to the ends of the lines. This is how real graffiti writers develop their unique signatures.
- Look into the history of "Blackletter" calligraphy. You'll see a lot of the same sharp angles and vertical structures used by monks in the Middle Ages. History repeats itself in weird ways.
- Try drawing it with different tools. A fat permanent marker gives a completely different vibe than a mechanical pencil or a digital stylus.
The S isn't just a scribble. It’s a bridge between generations. Now that you know how it works, go ahead and leave your mark. Just maybe not on the teacher's desk.