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Andy Warhol - Portraits That Changed The Art World Forever

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February 10, 2015

Andy Warhol and portraits – the collaboration with people of various backgrounds was the essential par of Warhol’s career. Some of these interesting personalities he welcomed in his New York studio, The Factory, and some he collaborated outside of this creative hub.

One common thread remained constant throughout his career – Warhol enjoyed making portraits, especially of celebrities and famous figures, those already immortalized, which he would elevate onto another level – a level of the pop icon. The 15 minutes of fame were not just a saying, or a belief, but a motto to live by. It’s somewhat ironic how Warhol’s 15 minutes have stretched into eternity, now that we appreciate him more and more for the genius disguised by the artificially created superficiality.

Our selection of faces Andy Warhol rendered will take you on a ride from TV to legend, from Hollywood to gutter, all of the popping out from the most various places we lay our eyes on today. If Andy were alive, he would’ve enjoyed it!

The video below is Screen Test 3 with Edie Sedgwick, one of Warhol’s favorite faces.

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Lenin - A Symbol of Revolutionary Change

Warhol’s Lenin takes the leading role in his wide series of portraits – he’s the protagonist of Pop art declaration of the end of Fine art. Lenin is simple, poster-like representation.

Warhol presents him as emerging from a black void, or fading away into it. He is, as the former leader of the Soviet Union, a symbol of possibility of revolutionary change of society, yet he is exposed without substance.

The painting is appealing, communicative and at the same time emptied of any political content. It’s not only that there is a suggestion that no distinction between art and other practices can be established, everything concerning the production of meaning in principle can be reduced to simple technology of making simulacra.

This technology is not specific to art. It is broader, and has the religious quality to it. The idea of God has resolved into an endless interplay of signs among themselves without any regard whatsoever to what was supposed to be signified by them.

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Moonwalk - The Momentous Achievement

Already with his early artworks, Warhol was recognized as “The Pope of Pop”, in that time, an experimental form where popular subjects are becoming a part of the artist’s palette.

With the story of one of the greatest achievements of the humankind represented in this work, Warhol just confirmed that the pop-artistic way of seeing at the world is constitutive of him as an artist, and  pop art is not just a fad, it has constituted itself as a paradigm.

He authored the Moonwalk Portfolio (consisting of two images of astronauts, one in pink and the other in yellow) to commemorate the momentous achievement of the first man on the moon. The pieces were created in 1987 only months before his death. That is also the reason why these works were never signed and the signature was printed afterwards.

This eminent image of an astronaut standing on the Moon with the US flag very quickly became an icon of the pop art and culture. It also represents the material that Warhol used to use for his images printed on vibrant, retro, poster colors.

Together with Norman Rockwell and Annie Leibovitz, Warhol’s Moonwalk image was part of the Smithsonian traveling exhibition that celebrated NASA’s 50th anniversary in 2008 and was subsequently collected in NASA/ART: 50 Years of Exploration.

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Mona Lisa - The Most Parodied Work of Art

“Don’t like this, he has just created brush strokes over the image. A child can do this just playing around”. This is one of the comments on the Warhol image of Mona Lisa on the official Andy Warhol website. “Of course any child could do this. Andy Warhol was very similar to a child. Children love jelly beans, Warhol loves images that have become jelly beans; the Mona Lisa is a jelly bean, Marilyn Monroe is a jelly bean….” – was the reply.

Although this communication is probably not between notable art reviewers, it still has the merit of giving a hint as to how we can interpret the (pop) art of Andy Warhol.

Pop art belongs to the movements in the history of art which render invalid the distinction between high and low art forms and make it rather non-existent. The original painting of Mona Lisa is often cited as one of the most renowned work in the history of art, and in the popular mind it has the status of “the most famous painting in the world”.

However, ever since Duchamp, it has become a target of iconoclastic art approaches, arguably the most parodied work of art, and Warhol didn’t miss the opportunity to give his contribution to this dialectics, by applying to the Mona Lisa item the same concepts of fame as in case of his fellow contemporary super stars.

Mick Jagger - Opposite and Tabooed Emotions

Mick Jagger, the Rolling Stones frontman, was another example of a pop-cultural icon Warhol was artistically related to. Jagger was a symbol of counter-culture, and Warhol was deeply implicated with the underground scene, and anything that was departing from the mainstream of sixties and seventies. This painting was done on the basis of photographs Warhol had himself taken of Jagger.

The quadriptych structure of the painting mimics to the extent the photographed representation of Jagger, and brings motion and action into it by the representation of photo session itself. Jagger is sensual, erotic, but in a way childish and innocent. His androgynous figure embodies opposite and tabooed emotions about sexuality.

There are also collage elements to it that function as a kind of veil to that exciting lust, desire and liberated forms of relating to the world.

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Shot Blue Marilyn - Memento Mori

Along with the Campbell’s soup cans, Warhol’s paintings of Marilyn Monroe, the ultimate celebrity, are the most popular works of his. The idea behind them is not shiny and light, especially if we take into account the fact that the most attractive representations of the actress were done after her untimely death in 1962.

The portraits stand not only as a symbol of American cultural history of the time but also as a reminder of its parochial, obscure, and above all brute side. Series of these Marilyns could be seen as a memento mori of an unexpected kind.

Shot Marilyn 1964 is a work of art produced by Warhol, and it consists of four canvases with a painting of Marilyn Monroe in various colors backgrounds: red, orange, light blue, sage blue.

Though there was an additional one with a turquoise base, but it didn’t undergo the same fate like other four. Namely, those four paintings were shot by Dorothy Podber. She suggested that those paintings should be shot, meaning photographed, but Warhol took it literally, and she did it with the gun. The rest is history.

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Triple Elvis - A Phenomenon of Fame

Elvis Presley, the icon of the 50’s, and a sex symbol, whose fame was overshadowed by other countercultural figures and performers in 60’s and 70’s, became not surprisingly a subject matter of Warhol’s work. Warhol was analyzing phenomenon of fame, its durability and alienated nature as simulacrum.

The Triple Elvis is presented as the overlap of three same images of Elvis as if he was exposed to the strobe light. Cinematic character of this image is obvious and reveals Warhol deep interest in motion picture and its ontology. The movie functions as a vehicle of fame. Its ability to convey excitement and drama is unprecedented.

The image of singer is sourced from the movie of typical title Flaming Star (1960). Western genre of movies put forward macho identity that came under severe criticism in the culture of subsequent social movements and Warhol’s take on Elvis exemplifies that different sensibility.

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Liz #5 - A Muse

Liz #5 – the name speaks for itself – one of many, fifth in the series. The number of paintings reveals to us that Elizabeth Taylor was a never ending source of inspiration for Warhol. And, as it appeared later, this inspiration led to never fading success, as paintings were priced around 30 million dollars.

Warhol never flattered Liz and this holds for Liz #5 too. He allowed its silkscreen technique to express each Elizabeth’s flaw, although there were not many on her divine face and figure. The photo which was the source for this pop art icon was taken at the time when Liz was very ill from pneumonia and with that in mind, Elizabeth’s smudgy lipstick and heavy eye shadows seem to justly point out the battle she fought for her life.

In the same manner, Warhol worshipped fame and celebrity in his work, Taylor was unconditionally committed to her fight against AIDS and for LGBT rights. This only strengthened their relationship. She was a muse for his art and he was a muse for her activism – they both had a friend who inspired them for what was most important to them.

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Mao Tse Tung - An Ambiguous Attitude

Warhol showed a great deal of interest in the political goings-on of his time and historical events. Once he said: “I have been reading so much about China. They’re so nutty. They don’t believe in creativity. The only picture they ever have is of Mao Zedong. It’s great. It looks like a silkscreen”.

He created a portrait of the communist leader based on a photograph from his famous Little Red Book. Warhol was caught by this topic at least partly because of the media’s attention to the opening of diplomatic relations with the People’s Republic of China in the early 1970s.

His attitude toward China was ambiguous. That is apparent on the surface of the painting. Graffiti-like representation of the Chairman Mao is at the same time negative comment on the authoritarian propaganda and censorship in People’s Republic of China, and sarcastic comment on the American society, self-seduced by its own ways of exercising control over population, that is to say, by its ability to recuperate any dissident gesture into a mainstream.

This idea of meta-censorship is palpably captured in this typical aesthetization of Mao’s portrait. This particular piece is housed in the Art Institute in Chicago.

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Self Portrait 1986 - The Face of the Ultimate Pop Icon

It was well known that Warhol almost inseparable from his camera. He ended up with numerous collections of photographs of people he took throughout his life. And we enumerated only some of the people that have found way to his paintings via photography.

But Warhol was interested in self-portraits as well and many of them included his drag and crossfit appearances. He started making self portraits in the 60s and during the years he went through several phases, and during the same time he exercised various appearances and identities.

This self-portrait with his head levitating in the black void with overstated wig is made in 1986, just before his untimely death. He also left instructions on how we should understand his work.

If you want to know all about Andy Warhol, just look at the surface: of my paintings and films and me, and there I am. There’s nothing behind it.


Warhol no doubt established himself as a ultimate pop-cultural icon, and his statement is that artifice is central to the all walks of life be it culture, politics or religion.

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Basquiat - The Intimacy

They were one of the most controversial art duos during the eighties and years after their death they still draw our attention. We could use the utilitarian arguments and say they were, in some sense, exploiting one another, but to exclude any romantic notions from their relationship just wouldn’t be fair.

They started collaborating in the early 80s and painted a number of works together. Warhol was usually the one who painted first, giving his college the opportunity to layer over his works.

The parallel could be moved between those paintings and the oxidation portrait of Basquiat by Warhol. He urinated on the canvas, which, combined with metal, originated rare polymorphous shapes. To make a “jelly bean” out of this story, you have to admit that, if someone makes a portrait of you, then piss on it and make it an unbelievable and unique artwork, you have to believe there must be something there.

The intimacy of this work can only be compared with the “permission” Warhol gave to Basquiat when it comes to his layers.

All images used for illustrative purposes only.