Sunday Mailbag

June 23rd, 2013 | Posted in Mailbag

Q: Do you ever get tired of drawing smiles? You know when you have a lousy day and all there are all big toothy smiles… has there been a day where you were just sick of it? Also, what’s your favourite expression to draw?

A: You are obviously referring to drawing live caricatures with this question, so I will answer from that perspective.

First, the short answer: no, I don’t get sick of drawing everyone with big, toothy smiles because I don’t draw everyone that way. I draw a caricature of THEM, and the specific smile they give me/have. In some cases I don’t draw them smiling at all. If you are getting sick of drawing big smiles on everyone, you should step back and decide if you are forcing big smiles on people’s caricatures when they do not belong. Given the diversity of the subjects a live caricaturist gets, you should never get bored or tired of drawing a certain type of feature or expression, because you should be being presented with an infinite variety of each… unless you are drawing at a “big, toothy smile” convention. Then I pity you.

I understand what you are saying, however. Drawing smiles on everyone, toothy or not, will get tedious if you don’t allow yourself to NOT draw a smile when it’s warranted. When doing live caricatures I live by the theory that I always draw my subjects smiling unless they give me a reason not to. I think in general most people are reasonably happy, and most want to appear to be happy in their drawing. These are supposed to be humorous depictions of people, and drawing people smiling naturally makes the drawing lighter and more appealing that way. I will always start my drawing intending to make the subject smile. I don’t pretend I know what their smile looks like, however. Nor do I shoehorn a generic big smile in to add humor when it doesn’t belong. I have a few goofy tricks I use to make my subject give me a smile right away… usually it’s a silly joke or comment, or I wiggle my eyebrows at them, or just give them a big smile myself. Smiley people react to that and show me their smile, which is what I want to capture. Sometimes it’s big and toothy, sometimes no more than a wry grin. A smile is as individual as a nose, so I strive to get it right. If they do not react, or don’t give me a smile, I don’t draw them with one. Some people are not smilers, and to draw them smiling would not be a good caricature. When that happens I give them the expression they are giving me. Engaging them in conversation as you draw helps… people will assume their usual expressions and mannerisms when talking. They seldom do when intentionally posing.

Finally, I do not have a favorite expression to draw. I like drawing people, and capturing the expressions that best represent their personalities. I guess that makes my favorite expression to draw the one that is right for the person I am drawing.

Thanks to Anne Lee for the question. If you have a question you want answered for the mailbag about cartooning, illustration, MAD Magazine, caricature or similar, e-mail me and I’ll try and answer it here!


  1. Leandro says:

    Nice advice! Quick questions if you allow me:
    1 – Do you care if the “target” will enjoy your caricature?
    2 – Do you make your style a little bit lighter when its a woman in front of you? (we know that they’re “vainer” and concerned about it than men).
    Thanks Tom!

    • Tom says:

      1. Yes, of course. They are the customer. they have to like it.
      2. I am “softer” on women mainly because I want them to look feminine, and that requires softer lines, features and less angular lines. I exaggerate maybe a LITTLE less, but not really.


New profile pic courtesy of my self-caricature for the Scott Maiko penned article “Gotcha! Mug Shots of Common (but Despicable) Criminals” from MAD 550

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