Are you there Joan Cusack? It's me, Joanna.

Updated: Aug 29, 2020

I'm struggling to draw a face.

You are looking at one of my first attempts to draw Joan Cusack from the 1980’s film 16 Candles.

If you didn’t recognize it was her, you wouldn’t be alone. The sketch ended up in the recycling bin, along with many other failed attempts.


The drawing is part of a series I’m working on. Its just one of the many Joan Cusack characters I’ll be illustrating. The task may not sound like much of a challenge for someone who has spent most of their life drawing. I practice a great deal in my free time, and it was also my major in college. So after 4+ years of making drawing my life’s focus, I should be able to put pencil to paper and presto! Joan Cusack!


Many failed drawings later...

As it turns out, it took many more tries to get to a portrait I am happy with. Don’t believe me? Here’s a snapshot of my kitchen table with all the source material and sketches strewn out.

By the looks of it, you’d think it was a mood board created by an obsessed evil genius who is plotting to make a Joan Cusack robot.


Throughout the drawing process, I felt like I was spiraling… getting farther and farther away from the portrait I was trying to create. Had I forgotten how to draw? Can I learn again? Did I ever know how to draw in the first place?


This, in case you are wondering, is the opposite of the ideal “zen flow” state a person hopes for in a drawing session. All of this frustrating trial and error got me wondering, what’s so tricky about drawing a portrait anyways?

My first drawings of faces

“Wow. You can draw faces? That is the hardest thing to draw”. That’s what my classmates used to tell me. Throughout my life, from elementary school through college, I could be found doodling pictures during class. I would sketch anything around me; a chair, a ruler, an overhead projector (remember those?), right down to drawing the pencil, itself.


My favorite thing to draw was people. Fortunately, there are lots of portrait subjects in the classroom. If you were to flip through one of my old notebooks, you’d find sketches of my classmates, mostly the back of their head and shoulders. As my classmates sat attentively listening to the teachers’ lessons, I was putting in my 10,000 hours to becoming a skilled artist.


More than a pretty face.

What my classmates didn’t realize is that drawing faces isn’t nearly as astonishing as it may seem. Faces can be broken down into proportions and basic shapes. There are charts and simple techniques for mapping where to place the eyes, nose, and mouth. With a little practice and studying, the process of drawing a face is demystified.


If drawing a face is so simple, than why is drawing Joan Cusack's likeness so tricky?


Because drawing a face and drawing a particular persons' face is an entirely different matter. It takes a keen eye to notice the details that make a person uniquely themselves. It’s the little dimple in someone’s chin, or the shadow that forms at the corner of their lips when they smile.


When someone’s likeness is captured, the drawing becomes more than a collection of well rendered facial features. The person’s individuality shines through in the portrait.

Drawings are illusions

I'm sorry, I can't use the word "illusion" without quoting one of my favorite t.v. characters, Gob Bluth. Just a warning for parents, Gob's language may not be suitable for children.

Now that I got that out of my system, let me share something a wise figure drawing instructor once told me. They described drawing people as “telling lies in 2 dimensions”. I took that to mean, that for a drawing to appear realistic, it merely has to make the viewer perceive accuracy. When done expertly, a drawing can make you momentarily forget that you are looking at a flat surface.


Sometimes the "truth" of a subject can only be uncovered with a little finessing. Take for example another one of my attempts to draw Joan Cusack. This drawing began by tracing a photo on a light board. I traced tiny details, from her frizzy wisps of hair to the folds of her ear. I was so precise. I included everything. Surely this would be a successful drawing.



Whomp. Whomp. The traced drawing would ultimately go in the recycle bin with the rest of them.


Tracing a portrait can go wrong in several ways.

For starters, sometimes a photograph doesn’t translate into other mediums. Joan’s forehead was too large, but why? I had traced it! Remember what I said about how we only have to perceive something to be accurate? It goes both ways. Sometimes a person can be drawn with technical precision, and it still feels off.


Another challenge of tracing is deciding which lines to accentuate. When tracing, its easy to fall into the trap that I did, where you try to capture as much information as you possibly can. In reality, while our brains are sophisticated at analyzing faces, they tend to focus on some areas more than others. When drawing freehand, it can be easier to intuit what those key features are.


Tracing seems to give equal weight to all the features, and in doing so removes some of the subject's unique qualtities.


The Parthenon

Drawing isn’t the only art form that involves visual trickery. When the Ancient Greeks built the Parthenon, they understood that in order for the structure to look visually “correct”, they would have to skew certain aspects of the architecture. For example, the columns on either side of the façade are slightly wider apart then those in the center, so that when viewed from the front they look evenly placed.



Another adjustment the Ancient Greeks made was to the foundation of the Parthenon. It grades ever so slightly upward towards the center. Though it curves, it appears flat when viewed in relation to the other structural elements.


If this doesn’t sound mind blowing coming from me, take a few minutes to watch this PBS NOVA snippet. You will do a double take when you watch some of the optical illusions in the video (seriously, I rewound a few times).



Isn’t it amazing how easy it is to pick out a friend’s face in a crowd?

As humans, we can recognize and recall hundreds of faces. Just think of all the people who say “I’m bad with names but I’ll never forget a face.” I mean, really? They can remember a complex combination of unique facial features which are subtle and barely detectable to the conscious mind, and yet remembering the name “Jessica” is too hard? Its kind of crazy when you really think about. Which I have. A lot.


On the Smithsonian’s website, there is a fascinating article about a 2014 study on facial recognition done at the California Institute of Technology. Maybe you are thinking "that sounds boring, I’m not gonna read that article." Let me sum it up for you.


Monkeys in a lab were connected to a machine that records neuron activity. They were then given images of human faces to look at. Scientists started seeing patterns, showing activity in specific neurons was linked to certain facial characteristics. Over time, the pattern was so well established, that the scientists could show the monkey an image of a face (randomly chosen from over 2,000 possible images) and tell which face they were looking at based on what neurons were firing!


I don’t know about you, but I think that’s pretty amazing. With all the sensitivities humans have to faces, its no wonder that we can inherently sense when a portrait doesn’t look right. My drawing of Joan Cusack may have all the obvious facial characteristics, but still it misses that certain je ne sais quoi that makes her recognizable.


Even Pablo Picasso sometimes struggled with drawing.

It’s been said, that Gertrude Stein sat for Pablo Picasso 80 or 90 times before he completed her portrait. While the exact quantity of sittings may have been exaggerated by Stein, historians do know that Picasso began the sessions in winter of 1905 and they dragged on till spring of 1906.


I read that he painted over her face in frustration, exclaiming "I can't see you any longer when I look". I am pretty sure every artist has felt this way at one time or another.


It was only after taking a summer holiday in Spain that Picasso returned to Paris and completed the portrait, this time from memory. And it was then that he finally felt satisfied that he’d captured his friend Gertrude’s presence.



Famously, when critics would remark that the finished painting didn’t look like Gertrude Stein, Picasso would reply, “It will”.


A little perspective.

I called a friend of mine who happens to be a talented artist. He draws comics, which has always impressed me. To think, I am struggling to draw ONE portrait, while he draws the same character hundreds of times in hundreds of settings, moods, and positions. It astonishes me.


When I asked him for a little advice about drawing, he said quite plainly “You seem to be under the impression that these finished works of art you see on the internet are the artists’ first try.”He was right. I am so used to scrolling through impressive works of art on social media, and don't stop to think about the failed attempts that I'm not seeing; all the"meh" work that paves the way to better work.


And so it goes. If Picasso can spend over a year on one portrait (and Gertrude Stein can spend almost as much time sitting for one), than surely it won’t hurt me to spend a couple days with Joan Cusack photos strewn across my drawing table. It doesn’t matter if I have to make a dozen Joan Cusack drawings, as long as just one of them captures a glimpse of her characters’ lovable, awkward self.


And you know what? I think this one does.

Authors Note: It takes more than practice to make perfect.

Stick around for future blog posts, where I try out drawing techniques from illustration handbooks. I'll share the tips and tricks that I like best.

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