Caricature

Let's say 2025 is going to be "the" year for drawing...

Jan 01, 2025

… and this is post #1 in this new adventure!

Let’s start off with the highest bar. (This way, it’s going to be all downhill from here on, in the sense of easier, not worser :)

A proposition: Caricature is the hardest art.

Caricature is not the same as portraiture. A portrait artist has to be able to create a good likeness of the person, which is no mean feat because likeness is not just an exactness as to size and shape of nose, eyes and mouth, etc. You can do that by tracing a photograph or using a pair of callipers. Likeness means capturing a personality by finding the inflections; the little creases, bulges and shadows that make that face, that unique person - the subtle, ambiguous “smile” of the Mona Lisa is a good example.

Caricature is even harder than portraiture because it must capture the personality in an optimal or more efficient way. By focusing on distinguishing features, the caricaturist makes the person completely recognizable with simplified and often very exaggerated drawing.1 It has a comical, often satirical effect. It is portrait and cartoon at the same time.

Let’s look at a few examples:

Hirschfeld

Albert Hirschfeld is, for me, the greatest caricaturist of all time. What makes him stand out is not just his uncanny ability to capture the character of a person, but how he does it with so few lines and often quite severe exaggeration.

For reference, here’s what Mr. Lemmon looked like.

Levine

The great David Levine also stands out. Since 1963, the New York Review of Books has published over 3500 of his drawings. Again, both spareness of line and imaginative distortion, posing or props make Levine’s work both witty and highly original.

For reference, here is a photograph of Mr. Douglass from the Wikipedia page about him. (Also an interesting read btw.)

Sorel

Another terrific caricaturist is the great Edward Sorel, whose dragon’s lair (studio) was fearlessly entered by Substack knight errant

Jason Chatfield

, a legend told on his excellent Substack New York Cartoons.

Edward Sorel’s cover for the April 1966 issue of Esquire, which contained Gay Talese’s article “Frank Sinatra Has a Cold.”. Screen capture from New York Times on 01.01.25. The article is full of details about Sorel’s upbringing and training too.

Here’s Sorel’s version of Frank Sinatra. Sorel draws on vellum, Mr. Chatfield reports, because it’s slippery, allowing Mr. Sorel to fluidly make all those back and forth, loopy loop lines.

I’ll assume you know who this person, Frank Sinatra, is when you see them. But then, maybe I shouldn’t assume.

I’m noticing that all these personages above and their drawers are “of a certain age,” that is, mine or older. Caricature depends on you knowing what that person looks like. Not surprisingly, the subjects are usually politicians or celebrities.

But then, I’m wondering, is caricature a “old fashioned” art form that will pass with the generations for whom print media and celebrity were more “consolidated” let’s say? Are there younger artists doing caricatures of younger persons of note?

I searched up “Drake caricature” just to see, and came up no particular caricatures, but instead several YouTube videos about how to draw a caricature of the rap artist Drake, including this one.

It is hard to say who the artist is. The video channel is called Easypicturestodraw, has 345,000 subscribers and has posted 2805 videos since 2012, which have had over 85 million views. Is this the new shape of caricature?

Screen capture from link to YouTube channel EasyPicturestoDraw on 01.01.25.

I try my hand at caricature

Back in 2020, during those hard days around the US election, I, like so many people, got kinda obsessed with ole’ orange face. I was doing satirical cartoons like just about everybody else.

Did the torrent of ridicule turn the tide in 2020 so that Biden edged Trump out. No, I don’t think so. It was very close, just as 2024. Could have gone either way imho. (I will be posting a theory about why criticism never sticks to Donald Trump shortly.)

Here’s my caricature from 2020 of Mr. Trump draped in the flag.

And here’s a Levine caricature I used for reference:

Screen capture from Swann Gallery auction site on 01.25. Note the diaper. :)

I did many terrible attempts before resorting to looking at Levine. I did look at photos of Mr. Trump online but I wasn’t about to trace. They are all terrible.

I like to think that if you know someone to see them, as in you would recognize them on the street, you should be able to draw them without referring to either a photo or the person being actually in front of you, in the same way you should be able to draw a table without looking at one. Maybe I’m wrong. The evidence suggests that for me at least, I’m wrong. A good caricature requires really good observation, patience and insight. It’s impossible to explain fully. It is an art.

I’ve drawn quite a few “Donalds” since then. (He is a persistent bugger though isn’t he!)

And then I had a revelation.

It was within the few months before the 2024 election that I noticed the smirky sort of chagrin face Mr. Trump puts on when he doesn’t quite know what else to do (which, as we know, is quite often). It reminded me of my all time fav cartoon character, Charlie Brown.

I posted about it here, with my own cartoon take off of the classic Lucy and the football gag, and a link to the story of a Schulz cartoon about Linus running for school President.

The unexpected takeaway from this Charlie-Donald observation for me has been that a caricature can be very simple. It does not need to fully capture the features of the person but can be reduced to cartoon-like signifiers. The hair, the tiny hands, the roundy, stolid body in a suit. Thus, playing around the other day with Mr. Trump and his ridiculous long red tie (another signifier), I came up with this:

In the first sketch, the tie just didn’t end. I was going to make it touch the ground but then I just stopped before making the pointy end. It seemed cool to just leave it, like an open question. Also the white space kind of split Mr. Trump in half, which seemed interesting.

Then I thought of adding red to the tie, and the tie bleeding. Then I did a full color version. Then I went back to the b/w version with the red now leaked out of the tie. And then finally this, finished art:

Like a lot of my cartoons, the meaning of this image is a bit confounding or oblique, let’s say. The news this week was about fractures within the Republican base but I don’t see the cartoon as being about that.

A good friend with whom I often share images before publishing them, said the red made him think of Mr. Trump’s promises to seek revenge and how it might backfire. I don’t see the image that way either.

If you notice the knot in the tie is heart shaped. That was on purpose. I think for me the idea was of a chagrinned Mr. Trump, the red draining out of his heart.

I’d be curious to know how you “read” the image.