My Top 5 Jean-Michel Basquiat Paintings

Artist Jean-Michel Basquiat Holding Engagement Ring

Words by Sammy aka @___SAMO aka Sampira

I’ve always had a strange relationship with the art world. I grew up in single-parent family. My dad still lives in the flat I grew up in. By definition, in the society we live in, I should never have been into high art. Or ever knew about it. 

We always try and skirt around this issue and say that’s not true. We live in a meritocracy, and everyone gets exactly how much they work for. But… in the age of being completely honest, we know this couldn’t be further from the truth. 

It all depends on how you come into it. I used to sit in the library at school, to avoid bullies. I read book after book after book. When I ran out of all the horror and the history, I turned to the art books. I started reading about Witkin and people like Matisse who had a different way of thinking. But they were still all white and rich. So there was a disconnect. 

Then, there was Basquiat. 

Jean-Michel Basquiat’s face stared through my soul. He was a Black man. He did graffiti. He was outspoken. He had background noise and was making art in his own way. His relationship with the art world (one of his pieces sold for 110 million, the most expensive piece sold by an American artist.)

I have a real obsession with outsiders going on to redefine the value and form of art. It’s often the outsiders that have the most to say, in the most interest ways. They make things we’ve never even dreamed of. It’s because they didn’t grow up in the arts. They weren’t taught the rules, and neither was I. My love for Basquiat goes deeper though. He was Black mixed race like me. He was self-taught like me. There’s so many parallels. He used very abstract images to explain himself, but he was very specific about what they meant. He know his vision so clearly, even if it wasn’t clear to others. 

Here are my 5 favourite pieces. 

5. Untitled (1982)

Untitled (1982)

I think it cements his whole identity, as an artist and a person in the world. It’s also the piece that proved everyone wrong. It sold for $110 million in 2017, making him the most expensive American artist. Yeah, not Black artist, just American artist. This solidifies this piece for me. He did it. He did it for all the streets kids. Completely cut across every single elitist, intimidating, exclusionary art gallery and institution. A self-taught graffiti street kid of Haitian and Puerto Rican descent, did it bigger than anyone. I was so happy when it happened. 

The piece itself, probably isn’t Basquiat’s strongest, honestly. But the aesthetic and the brashness of it, encompasses everything that Basquiat had become in the public eye. There’s very little thematic significance to this piece (i think there’s definitely something deeper BUT, he had far more significant social commentary in others.). But what it has done for his legacy, and the statement to kids that just work on instinct, is monumental. For those who want to craft impactful art just like this, they can do so by practicing the right technique and getting the latest equipment. That’s why it’s best to now start researching about details like a drawing tablet price.

4. Obnoxious Liberals (1982)

It’s probably the most “political” Basquiat is at, if you ask the art scene. It was a direct comment on the rich arts scene at the time. It was signifying their relationship between artists like himself, who had come up from the streets, and how they treated him, in their elitist attitudes. After, when he started getting acclaim, they would swarm around him, but he had a long memory. It’s a direct, to a point, tongue in cheek critique that they were so hallowly hungry for art, that they would allow themselves to be parodied by an artist they had racially and socio-econimcally cast out. He makes his own stance very clear as well with slogans such as “not for sale” and dollar signs, directly challenging the notion that art should be capitalist. 

3. Tuxedo (1982)


It’s striking in the way it defies Basquait’s uniform he stitched for himself. His iconic crown is sprayed on the top of the paper and it shows his influences boldly. He loved hip-hop, scat music and poetry. He worked in symbols and poetry and it’s no clearer than here. It’s probably his most abstract work. He often put social commentary through art into his work. The crown, I think, isn’t something to be celebrated. He’s not calling himself a king. He’s using it ironically to symbolise the inequalities he faced. How can you wear a crown if people are dying? Shine it up good, make it twinkle. So we’re not seeing a person wearing a tuxedo, we’re seeing what he thinks a tuxedo is figuratively. 

2. Riddle Me This Batman (1987)

Riddle Me This Batman (1987)

Riddle Me This Batman was made with acrylic crayon on paper. It shows Robin and Joker, but it completely subverts it. I think he’s making a comment on us as a society and who we put our stock in. Growing up in New York, he definitely saw his fair share of corruption and brutality. I always think he’s commenting on our societal need for a hero and a villain; we can never just be… We can never create revolutions as citizens. We always expect someone to rise up and we follow them, to buffer the damage. The same as calling out injustice or defeating evil… We always need a Batman. He subverts this, crossing out Batman’s emblem twice, and portraying Robin as a drunkard. 

1. Untitled (Fallen Angel) (1981)

Untitled (Fallen Angel) (1981)

I’m not an OG fan. I learnt about him when his work came with the Boom! For Real exhibition at the Barbican, but I instantly felt connected to him. Like an old friend. Untitled (Fallen Angel) is one of the most striking paintings I’ve ever seen. I was struggling badly with my mental health, and the painting alleviated some of that, which is monumental. It’s a mix of pain and freedom. It says, to me, that freedom is beautiful to the oppressed, but the white and upper-class supremacist system sees us as monsters when we do fight for our freedom. It gave me a lot of comfort when I was struggling with whether to assimilate or go my own way. When I learnt about Jean-Michel and where he had come from, I decided to go my own way and never looked back. 

Jean-Michel Basquiat is a testament to talent. People have often commented on “talent being in an unexpected place” but that is rooted in racism. they said the same about Alexander McQueen, and it was deep rooted in classism. Basquait is enigmatic, passionate, multi-faceted and he left us way too soon.

He died of an overdose, brought on with the struggles of fame within the art world. He was being lauded by the same people who were calling him racial slurs behind his bag; an absolute madness to deal with. He died at 27, a year younger than me. I think about that alot. All the art he’s left. What he would have said about the world today. Maybe that wasn’t written though. 

As so many great artists leave young, maybe we were only supposed to have his greatness for a short time. To spark the next minds and then leave. To tell us, in his very short life, what street kids were capable of, and not to take it too seriously. Keep that tongue in cheek spirit with the critiques too. And give it to them, every single day, the only way a street kid can. 

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