Why I Like Drawing Portraits Live

Why I Like Drawing Portraits Live

When you watch a talk show or hear a speech, do you like it better live or rehearsed?

Just think about that for a moment.

Your and my political opinions aside, there is a reason why a certain candidate for president has such a large following. People like spontaneity. It can be dangerous sometimes, but it has a way of reaching, relating to people that something planned and rehearsed cannot.

Last Saturday, I signed up to share a tent with three fellow artists at Artisan Forge Studios at the Artist’s Market held in Phoenix Park, here in Eau Claire. It was an absolutely beautiful day–sunny, not too hot, with a gentle breeze.

A perfect day for doing drawing live portraits.

We got set up at around 7 am, and things were slow for the first couple hours.

Then, around 9 am, things really took off. The market was starting to get busier with more people passing by every minute. I asked one my fellow artists to sit for me and I did a free portrait of him to “prime the pump.” That portrait broke the ice and soon enough I had a small line of people interested.

I ended the day having done several portraits and the last drawing was 4 faces on one paper!

Here’s why I love doing live pencil portraits (though I still like drawing from photos too.)

1.  It keeps your drawing skills fresh.

Capturing a person’s likeness in about 10-15 minutes is not easy, especially when they move around. (I often find that children hold still better than some adults do!) In addition, the challenge of seeing a three-dimensional person and transferring them to a two-dimensional paper preserves and strengthens your overall drawing skills. Again, doing drawings live is not as precise as doing them in a studio environment from a photo, but the exercise helps keeps your creativity from going stale!

2. It’s a great way to meet build relationships and meet new prospective clients.

Some of the folks I have done live portraits for have asked me to do larger, more detailed commissions from photos later on. Or, alternatively, others who don’t have time or don’t care to have their portrait drawn live pick up a business card and contact me at a time that’s more convenient for them. While drawing portraits, I enjoy chatting with the person I’m drawing and get to know them a bit. It’s a fun time!

Portrait artist Matt Philleo doing live pencil portraits at Artist's Market in Eau Claire.

Portrait artist Matt Philleo doing live pencil portraits at Artist’s Market in Eau Claire.

3. It kicks perfectionism in the teeth.

When you have a line of people waiting, you don’t have time to fuss over every detail in a portrait. A perfectionist by nature, it goes against my grain to have to crank out a portrait so quickly, knowing it has many flaws, but it is good to be able to do that once in a while. I am continually amazed that, while creating a portrait, I can see that I didn’t capture the likeness as accurately as I wanted, but most of the customers are just thrilled with it. Well for $10 or $15, they aren’t expecting a Rembrandt, and they probably just think it’s cool to have a decent sketch of themselves or their kids done live in just minutes.

4. It helps pay the rent.

I charge $10 for a single face on an 11 x 14 paper, and $15 for couples both of which take less than half an hour. Many customers like their drawings so much they frame them and give them as gifts. It’s a nice value to the customer for a very low price. With that, I can do close to 25 portraits on a really good day. That all helps to pay studio rent and supply more papers and pencils!

5. It’s fun to be outside doing art.

Do I need to explain more?

As of the writing of this post, this Friday I plan on being a part of the Untied Special Sportsman’s Alliance Summerfest Event held in Pittsville, WI. This is an event that caters to children with special needs, offering them a variety of sports and activities from archery to horseback riding. Everything there is free. I will be doing live portraits there, with the goal of capturing the beauty of these children and bringing encouragement to their lives.

I will let you know more about that after the event takes place!

Share Your Thoughts!

If you have any comments or questions about this post, please leave me your feedback below! I will personally get back to you. Can you help me spread the word? Please share this post with your family and friends by using the social media links on the side or below. Thank you!

"I have inscribed you on the palm of my hands."

Inscribed6a 500px

"Inscribed," Pencil on Paper, by Matt Philleo

One day, when I was discouraged I read a verse in the Bible, in Isaiah, 49:15-16, where it says, "Can a woman forget her nursing child And have no compassion on the son of her womb? Even these may forget, but I will not forget you. Behold, I have inscribed you on the palm of my hands." This verse brought such encouragement, that I created this original work of art to share the incredible love of God with others, including you!

Get a free 8 x 10 copy of this drawing that you can use to print, share, or as wallpaper!

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  1. Dear Matt, It has always been tough being an artist for a paid market. And probably portraiture might be the most demanding. There are popular styles which dictate as well as the great downside of working from photographs. The patron most often demands a “photo-copy” done in a medium. A true portrait artist works “from life” and is free to interpret what he sees and feels into his final image. Most working from photos cannot make a likeness from life. They are mere draftsmen. Probably the greatest portrait photographer has been Karsh of Ottawa. But I can remember when his early work was called “pore” photography because of the element of realism he added. Yet all the great people of his generation hurried to his door for a Karsh portrait. He even went to Britain to photo JB Shaw! Portrait art is indeed a noble art. And few “artists” are capable. Even the greatest have sometimes taken months to attain the correct likeness of personality in their viewpoint. I applaud your work outside the studio. Eric Westhagen

    • Hi Matt!!! When I was a kid, a really good vacation idea was New Orleans. We loved Jackson Square so much! Back then, all around the square, artists would set up their easels just like this in your picture, and people would sit for live drawings. We were walking by one such artist one day while on vacation, and the artist summoned to my mom to allow my younger sister Denise to sit down. She was quite fetching when she was a child; Large brown eyes and kind of pinkish red hair, and freckles galore. He did the most wonderful oil of her in just about a half hour. We kept it in the family for years; I’m not sure what ever happened to it. What a wonderful experience that was! I also remember the wonderful powdery doughnuts we ate at that famous corner restaurant every time we went!! I’ve shared pictures that my late sister Darlene did; one of which had 4 portraits in one, just like you described. I would attach it here, but for some reason, my Yahoo mail has been malfunctioning, and won’t allow me to attach pictures. I will send it to you later. Anyway, thanks for this post! It was really inspiring!!!!

      • Matt Philleo

        Thanks, Donna! I would love to see a color portrait done live by an artist. That would be quite the experience. I think of how you mentioned the artist summoned to your mom to allow her daughter sit down for a portrait. I have found myself engaging the passers-by in that same way: encouraging them to get a portrait done if they show the slightest interest, without being pushy. It’s all part of the fun!

    • Matt Philleo

      Interesting thoughts, Eric. I have to admit most of the portraits I do are from photographs, and most of them are supplied by the client. I would have to trust that when I receive a photo from a client, it accurately represents the personality of the subject. Although I’m sure some do, a number of the photos I receive are of the typical “point and shoot” variety with the subject illuminated by a frontal flash. Inherently, it would make for a very flat painting–but I do my best to make it three dimensional and lifelike. Occasionally, I receive a few photos that have a more engaging light source and I can create a more lifelike, aesthetically pleasing portrait. I have also taken some photos of clients myself and painted from them. I still have yet to paint a detailed portrait (not a study) from life. I think that photography, even with its speed and convenience does not accurately interpret value, color, and mood as well as the eyes of a trained portrait artist. I’m still training myself to get to that level. Thanks for your comments!


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