Conversations with Missy: Anson Gordon

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The first time I walked up to Anson Gordon, it was not because I had a plan. It was because of his face. He was in the vendor room at the DoubleTree in Orlando during Creation Entertainment’s Supernatural: The Road So Far… The Road Ahead weekend, and he smiled at me like he was actually glad another new person had stopped. That is rarer than it should be.

We started talking about my denim jacket. He complimented it. I told him that if he liked that one, he should see my custom Bon Jovi jacket. He said he wanted to see a picture if I had one. I pulled out my phone. That is how the conversation started: not with a press list, but with a jacket.

From there we got to his art. The vendor room had gone quiet enough that I asked if he would be willing sit for an interview. He said yes. I am glad I asked.

Gordon is Jared Padalecki’s longtime friend, he called him his best friend on camera, and he had been to these conventions before, usually in the green room. Orlando was only his second time out with the work. His first vendor-room convention was Nashville, about a year earlier. He is still taking in the distance people travel, and the fact that some fans are on their 20th, 30th, or 40th convention weekend.

He is easy to be around. Kind. Humble. Funny in a low-key way. We talked on camera and off it, and the off-record parts are what made the on-record parts feel like a real conversation instead of a vendor-room stop. When he started showing me images of his other work, I had to pause. The emotion in the faces is not something you see in every art booth. He does not talk about the talent as if he is owed attention for it. He seems genuinely glad that anyone cares.The pieces that stopped me were the Lakota Sioux portraits. Gordon said he began working in charcoal less than a year ago, after a friend with a gallery in Austin asked him to put a piece in a South by Southwest event. He wanted that series to honor the Lakota Sioux. His artist page describes the same body of work as focused on Oglala Lakota and Dakota Sioux chiefs. In person, they read like old photographs pulled out of paper, not copies of pictures, but faces that look developed rather than drawn. That is his account of the process too. He said it felt as if he pulled them out of the page.

His method matches that description. He lays down compressed charcoal, then pulls the light back with kneaded erasers. He compared it to sculpting. He rarely uses a charcoal pencil except in places like the eyes. Prints of his work are at ansongordon.com. His Instagram is @ansongordonart.

What he brought to Orlando were prints of the portrait Jared commissioned for his birthday. Gordon said Jared had never asked him for anything, then asked for that drawing. He took it seriously because he knew it might be seen. Knowing his subject that well may have helped. It may also have added pressure. He said he was trying to draw Jared’s mind and soul, not just the face, and that the marks around the figure are “thought orbs,” the energy he associates with him in person. Jared then asked him to come on the road and show the work. That is why he was in the vendor room.

We also laughed about the part fans already know: Gordon had not watched a single episode of Supernatural. Knowing this, Jared decided to organize an online watch party of the pilot so fans could join them and raise money for a good cause. Gordon mentioned a parent of his is a teacher, and Jared has said publicly that a portion of those proceeds goes toward Amazon teacher wish lists. It only seems fitting.

October 4 flips the chairs. Gordon is going to try to teach Jared how to work in charcoal. The live online event, Getting Sketchy with Padalecki, is October 4 at 8 a.m. PT / 11 a.m. ET through Momentus / Shop Stands. Viewers can follow along at home. Anson said tickets were still available, and that one viewer will win a meet and greet with Jared. He has already posted a supply video so people who join can set up an easel and work in real time together. Fans voted on the subject. Gordon said there was a clear winner and that he was not naming it yet, only that every Supernatural fan would know what it was.

I walked up because he smiled. I stayed because the work is that good, and because he talked about it without making the moment about himself. Watch the interview. Then look at the portraits.

If you want more weekends like this one, check Creation Entertainment for The Road So Far… The Road Ahead dates. There are still 2026 shows, and 2027 tickets are already on sale. These conventions are one of the most direct ways to connect with the people from the show, and with artists like Anson who now travel with them. We will be in Nashville next May. If you are going, that is a good place to catch up with Anson, and with us. ~ Missy