When painting a self-portrait in oil, is 3rd time the charm?

It was for me.

This fall will mark my six year anniversary of learning how to paint with oil.  In 2019, I bought my first set of oil paints from Plaza Art in Richmond, Virginia, a month before my birthday, at the great encouragement of my girlfriend.

Earlier that same year, I had been studying portrait anatomy online at New Masters Academy, and as soon as I got into oil, I immediately set to work on large and small portrait painting.  I remember telling myself that each year, around that same time, I would commemorate my oil painting anniversary by producing a self-portrait.

Well, that was a nice, romantic goal to set for myself, but I never followed through with it.  Not in those first years at least. 

My First Self Portrait – 2021- 

If you may even call it that – was a bag of goldfish, I very ironically titled “Self Portrait”.  This was me invoking that quintessential millennial ironic detachment we briefly discussed last week in the posting your art on Reddit blog.

I did that a lot back in the day – it’s called being too cool for school, and it doesn’t typically age well.

So my first self portrait was a bag of goldfish (In my defense, I have always loved the snack that smiles back).

My Second Self Portrait – 2023

My first true attempt at a self-portrait.  This painting was executed in an ambitious fashion and with great expectation despite its small size.  Looking at the painting now (after not having done so in a year), I effectively stole all the compositional devices from Rembrandt and the tonalist painters.

A strong direct light dramatically illuminates one side of the face, creating a high contrast portrait with distinct shadow shapes being cast over the opposite side of the face.  This effect results in a very dramatically lit portrait illuminated against a dark background.  If you look at Rembrandt’s paintings, they are almost all composed in this fashion.  I believe this lighting effect was used to communicate the light of God shining down on the sitter.

Knowing me, I was probably pursuing this device to achieve a more Jungian effect with the intent of establishing a tension between the light side and the shadow side.  In effect, rendering a self-portrait that would work on multiple levels.

The Importance of Likeness

I liked this painting initially, but was soon convinced otherwise by those around me.  People didn’t feel like it possessed a strong resemblance to me, myself nor I.  At the time, I was a bit too close and too attached to the painting to really step back and assess its quality with any sort of objectivity (to the extent that that’s even possible).  If I remember correctly, I was even going to give this painting to my mom (as one would), but I felt too insecure given this whole likeness debacle. 

A question worth asking is: 

In order for a portrait to be successful, does it need to possess a strong likeness?  

What do you think? Certainly a discussion for another day.

I unearthed this painting from my scrap panel drawer in order to document it for this blog, and despite the fact that the likeness is lacking (even cartoonish!) I like this painting and am not likely to bring myself to gesso over it anytime soon.

My Third Self Portrait – 2025

Finally, a self-portrait to call home about – or in this case, to write to the internet about.  This was painted from a photographic reference taken at the Houston Museum of Fine Arts.  Some weeks prior to staging the photo, I had been wandering around the Nancy & Rich Kinder Building of the MFAH when this painting by Jasper Johns caught my eye.

The work by Johns is titled Ventriloquist, and upon doing some research for this blog, I was surprised to learn a very relevant detail:

“When Abstract Expressionism was at its height in the 1950s, Jasper Johns returned to concrete imagery. He painted simple icons: flags, numbers, and targets. In Ventriloquist, Johns arranges such imagery to create a symbolic self-portrait.” (1)

Ventriloquist, by Johns, is a self-portrait

Very relevant. I did not know that until right now, and I certainly did not possess that information when I staged the photo and painted the portrait (I should probably read the wall labels more to sound more smart and stuff).

What drew me to stage my self-portrait in front of this piece specifically was the two green and black striped American flags stacked on top of each other.  These bastardized flags (at least that’s how I interpret them), in conjunction with the Burger King crown atop my head, felt like appropriate symbols to articulate an American identity in distress.

I’ll leave it at that and let you interpret the rest.

I don’t like it when people hold me hostage and unsolicitedly tell me about all the “profoundly” hidden symbols and layered meanings baked into their art. Someone held me hostage once and after that, I vowed never to do that to anyone.

The Art of Looking

It’s one thing to look at something, one thing to see an object and register it as a “thing”.  It’s a completely different exercise in looking to represent that “thing” in paint.  This act forces the observer (the painter) to study the object, the scene, or the sitter in an entirely new type of way.

When painting a self-portrait, be prepared to look at yourself in this same way.  Be prepared to spend 5, 10, 20 hours staring at a picture of yourself while you render every detail, every turn of form in paint (if you’re into that sort of thing).  It’s really neither a good nor a bad experience; it’s just an interesting one.

Since the advent of painting, artists have been representing themselves and those around them as a means to communicate the human experience.  No amount of generative AI, Photoshop, and selfie sticks thrust onto popular culture will render this tradition obsolete.

If you are a painter who has yet to embark on the introspective journey of painting a self-portrait, I highly encourage it.

It’s never too late to thrust yourself into the long, unbroken chain of artists who throughout time have represented themselves in art.