Walk into any high-end gallery in Chelsea or a streetwear shop in SoHo and you’ll feel it. The ghost of a kid with a spray can is everywhere. Jean Michel Basquiat paintings aren't just canvases; they are visceral, messy, and insanely expensive documents of a New York that doesn’t really exist anymore. People see the crowns. They see the frantic scribbles and the "SAMO" tag leftovers. But honestly? Most people miss the actual point of what he was doing because they're too blinded by the $100 million price tags.
Basquiat was a disruptor before that word became a corporate cliché. He didn't just paint. He attacked the canvas with oilsticks, acrylics, and Xeroxed scraps of paper. It was a chaotic symphony.
He was 21 when he took the art world by the throat. By 27, he was gone. But in that tiny window, he changed how we look at "high art." He dragged the street into the museum and made the curators like it.
The Anatomy of a Masterpiece: What’s Actually Happening on the Canvas
If you look at a Basquiat and think "my kid could do that," you’re missing the layers. Literally. His process was subtractive. He would paint a beautiful figure and then immediately cross it out with a black oilstick. Why? Because, as he famously told interviewers like Tamra Davis, crossing things out makes you want to read them more. It’s a psychological trick. It forces your eye to work.
His work is full of anatomy. He was obsessed with Gray's Anatomy—the textbook, not the show—after a car accident when he was seven. His mom gave him the book while he was recovering in the hospital. You see it in the exposed ribs and the skulls. Look at Untitled (1982), the one that sold for $110.5 million to Yusaku Maezawa. It’s a skull, but it’s pulsing. It’s a map of a mind under pressure.
He didn't use traditional easels much in the beginning. He used doors. He used window frames. He used tires. Anything he could find on the street became a substrate for Jean Michel Basquiat paintings. This wasn't just because he was "poor"—though at the start, he certainly was—it was because he saw no distinction between the city and the art.
The Crown and the King
The crown is the most overused motif in modern fashion thanks to him, but for Basquiat, it was a weapon. He used it to "enthrone" people who were usually ignored by history. Black athletes like Joe Louis and Sugar Ray Robinson. Jazz musicians like Charlie Parker. By putting a three-pointed crown over their heads, he was forcing the viewer to acknowledge their royalty in a white-dominated space.
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- Irony. He often used the crown ironically, too.
- Power. It represented his own ego, which was massive and fragile all at once.
- History. It linked back to his interest in heraldry and ancient symbols.
Sometimes the crown is just three simple lines. Other times, it's ornate. It changes depending on the mood of the piece, but it always signals that something important is happening.
Why the Market Went Absolutely Insane
Let's talk money because you can't talk about these paintings without talking about the auction room. In the 80s, you could buy a Basquiat for $2,500. Today? You need a private jet and a sovereign wealth fund just to get in the room.
The scarcity is real. He produced a lot of work, but he was only active for about eight years. Collectors like Larry Gagosian and Bruno Bischofberger recognized the genius early, but the "blue-chip" status didn't truly solidify until the late 2000s. Now, he’s in the same league as Picasso and Francis Bacon. It’s a status symbol. Owning a Basquiat says you’re not just rich; it says you’re "cool" rich.
But there’s a downside. The high price makes people treat the art like a gold bar. They put it in a climate-controlled vault in Switzerland and never look at it. That’s the ultimate irony for a guy who started out writing "SAMO© AS AN ALTERNATIVE TO GOD" on the walls of the D Train.
The Andy Warhol Connection
You can’t understand Jean Michel Basquiat paintings without looking at his weird, symbiotic relationship with Andy Warhol. They were the "Odd Couple" of the 80s. Warhol was the fading king of Pop; Basquiat was the hungry prince.
They collaborated on dozens of canvases. Warhol would paint a logo—like the GE logo or a punching bag—and Basquiat would come in and deface it. Or "improve" it, depending on who you ask. Critics at the time, like Vivien Raynor, were brutal. They called Basquiat Warhol’s "mascot." It was a devastating critique that hurt Basquiat deeply. But looking back at those collaborations now, you see a fascinating tension between the clean, mechanical lines of Pop Art and the raw, expressive grit of Neo-expressionism.
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Decoding the Language of the Street
If you spend enough time looking at the text in his work, you realize he was a poet who happened to use a brush. He loved lists. He loved historical dates. He loved the "Drip."
He would have the TV on, a record playing, and a book open all at once. He would pull phrases from all three and mash them together. It’s why his paintings feel like browsing the internet before the internet existed. They are hyperlinked. You see a word like "TAR" and it links to "ROOSTER" and then to "PETROLEUM." It’s a stream of consciousness that demands you pay attention.
The labels aren't just labels. They are visual elements. He used words as shapes. He understood that the letter "A" has a different energy than the letter "Z."
Misconceptions About the "Graffiti" Label
Basquiat hated being called a graffiti artist.
He used the street as a training ground, sure. But his goal was always the gallery. He was incredibly well-read. He studied Leonardo da Vinci’s notebooks. He was obsessed with Cy Twombly’s scribbles. When people reduce him to "just a street artist," they’re ignoring the deep art-historical knowledge that informs every stroke. He wasn't some primitive savant. He was a calculated, brilliant artist who knew exactly what he was doing.
He was also a master of color. Even in his darkest pieces, there’s usually a shock of neon yellow or a bruised purple that holds the whole composition together. He used color to create a sense of urgency. Everything feels like it was painted five minutes ago, even though it’s been forty years.
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How to Appreciate a Basquiat Without Being a Millionaire
You don't need to buy a painting to "get" it. Honestly, seeing them in person is the only way to feel the scale. If you're in New York, the Broad or the MoMA usually have something on display.
When you stand in front of one, don't look for a "story." Don't try to solve it like a puzzle. Just feel the vibration of the lines. Notice where the paint dripped and he didn't wipe it away. Look for the footprints—he often stepped on his canvases while they were on the floor. These are physical objects. They are records of a human being moving through a room.
The legacy of Jean Michel Basquiat paintings isn't just in the money. It's in the permission he gave to every artist who came after him. He proved that you don't have to be "neat" to be profound. You don't have to follow the rules of perspective or shading to tell the truth.
He changed the aesthetic of the world. From Jay-Z lyrics to Uniqlo t-shirts, his visual language is the wallpaper of modern culture. We’re all living in Basquiat’s world now.
Actionable Ways to Engage with Basquiat’s Work
- Visit the Schomburg Center: They have incredible archives and resources regarding the Black artists of Basquiat's era.
- Read the notebooks: Princeton University Press published "The Unknown Notebooks," which gives you a look at his raw thought process without the "art world" polish.
- Watch the documentaries: "The Radiant Child" is the gold standard. It features footage of him actually working, and you can see the speed at which he made decisions. It’s terrifyingly fast.
- Study the "X" factor: Next time you see a word crossed out in a painting, stop and try to read it. Ask yourself why he wanted you to see it, but also why he wanted to hide it.
His work remains a mirror. If you see mess, maybe you’re looking for order where it shouldn't be. If you see beauty, you’re starting to understand the chaos. Basquiat didn't provide answers; he just asked better questions. He made the world look at the things it tried to ignore—the bones, the history, and the grit of the street—and he made us call it art. That is his real crown.
Keep an eye on upcoming retrospectives in major cities, as many private collectors are beginning to loan out these works more frequently to ensure the artist's legacy remains public and not just locked in a vault. The next time a major piece goes to auction, ignore the price tag and look at the brushwork instead. You'll see a man who was burning through life, leaving a trail of fire on every canvas he touched.
The best way to respect the work is to look at it for more than ten seconds. In a world of scrolling, Basquiat demands a stare. Give it to him.