The year 2020 gave us so many shifts in reality, not the least of which was Christmas. Like many families, mine did not gather together. The loss of our rituals was unsettling, but we created some new ones to fill the void. Oddly enough, I made a new friend for the season. And he kept me company in the studio as I painted gifts for his children.

Here’s the story. The commission came in during the second week of December. It was a fairly unusual request, but I’ve had weirder. The client brought a portfolio of photos of her late husband, and wanted two portraits (using the same source photo) — one painting for each of their daughters. I’ve painted deceased subjects before, working from photos without ever meeting the person. Generally, working from photos is fine … but not meeting the subject is a real challenge. As I explained to the client, every brush stroke is a decision …. moving the painting toward or away from the “feeling” of the subject. If the artist has no real sense the person to orient the work, it’s like wandering toward a destination deep in the woods without a compass. Lacking a well of experience to draw from, it all comes down to instinct …. and faith. I have no shortage of either, but even so, it’s VERY hard to do this kind of work well.

Having finished my other Christmas commissions, I accepted the assignment, and hastily prepped two 16 x 16 boards with portrait-grade linen over panel. While the canvases dried, I tried to discover more about this larger than life character everyone lovingly called Boss. His wife told me stories; so did the man who had served as his driver for many years. The source photo was one Boss had liked, in a dark, conservative suit. We decided to paint different ties for each painting, using ones with meaning for each of the girls, and corresponding background colors … one red with a school tie, and one blue with a whimsical, tropical tie.

Then the work began … two easels side-by-side in the upstairs studio where it’s so warm and cozy in the winter (I’m not sure I’ve ever loved a studio space more). My source photo of Boss was on a music stand in the middle …. always looking right at me, with tender gray-blue eyes …. and something else … something ineffable … growing in strength as the work progressed. I’ll come back to that.

When painting a portrait using the classical method …. building the picture up with thin layers of paint … the image emerges gradually. The underpainting, which is essentially a monochromatic drawing in paint, generally resembles the sitter, but rarely conveys the feeling of the person. In a way, that feeling comes together gradually, layer by layer. But for every single portrait I’ve ever done, there is a precise moment when the subject feels real. It’s not sort-of-real, then a-little-bit-more real, then more-real-still. Nope. The process of construction is gradual. But that moment of life happens in an instant. I always feel it, tingling on the back of my neck. Not a conscious thought … it’s a feeling. From that point on, there’s a negotiation of sorts … the person seems to respond to every mark … “yep, keep going” or “no, not so much”. The subject essentially tells me how I’m doing. Of course they do … at this stage they are alive, metaphorically.

That part … the moment of life … is normal for me. Moving along the process alone, then suddenly the person is there with me, and we carry on together. To be clear, I feel the vitality of the person, but I don’t feel their literal presence in the room. We are co-creating, but my studio-reality is not the same space as the subject’s painting-reality. They feel real, but they don’t feel present. That was always true, until Boss.

From the moment I placed his photo on the stand, he felt alive to me. Neck tingles from looking at the photo! Granted, portrait painters get a lot of information from looking at a person (or an image) … a lot more data than someone without an artist’s eye. (As a kid everyone thought I was psychic because I could always tell when people were lying … turns out, it wasn’t anything supernatural at all … I was just a portrait painter in the making.) But deriving gobs of information about a person from their image doesn’t make them feel present.

OK, you know the feeling of a presence in the room, right? Unlike solitude, there is the energy of shared space … even if you’re not interacting … you can feel another person in the space with you. Normally that’s because they actually ARE there with you. As I worked on these two portraits … softly at first, but growing in intensity … Boss was there in the studio. Bear in mind, doing two classical portraits in a week is no small task for me, so I was working every waking minute. The fatigue and pressure were enormous. Without the necessary drying time between sessions, I was painting wet into wet, which is an unforgiving technique. “A siege in the room.” The self-doubt is always there to battle; this time I was feeling it in my body … clenched jaw and aching shoulders. But my friend Boss always settled me down. His presence, and yes, it did feel like a presence, urged me on … “you can do this — you can — you can do this for my family.”

The client and I communicated about the work every day. Unlike many artists, I love collaboration, so her input was welcome and helpful. And as the feeling of Boss grew in me … as his presence felt more and more real, I finally broke down and mentioned it to her. I didn’t want to sound TOO crazy-from-the-world-of-weird (which is actually where I live, but try not to talk about it, since appearing sane strikes me as a useful professional characteristic). I toned down the experience: “ya know, I’m getting a feeling for him … I can almost feel his presence,” apologizing for sounding a wee bit psycho. Amazingly, it didn’t sound crazy to her at all. She told me stories of the many times since his death that people close to him had had the same experience…. “there was a recent wedding where everyone kept saying to me, ‘I can feel Boss here with us.’” At that point I was all in. If Boss was determined to help me, I was going to listen. And we worked on together.

I basically collapsed into bed late Christmas Eve thinking the two Bosses were finished, but someone woke me before dawn — “do a bit more”. So we did.

I delivered the Bosses to the client at 4:00 on Christmas day, and she gave them to the girls that evening. They were completely surprised, and thrilled with the work. Normally, presenting a portrait is a nervous business … never quite sure how the client will react. But this time was different. I wasn’t wondering how they would feel. I already knew — we had gotten it right, my dear friend Boss and me.

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