Blog / 2012 / How to Make Portraits More Interesting

Portraits tend to be most interesting to those who know their subjects, but there are a few ways to make this kind of painting more appealing to a wider audience.

Care about the subject.

Instead of just being about the subject, portraits actually represent the intersection of two lives. This means that the chemistry between sitter and artist is on display, and also that it’s useful for an artist to be a little bit in love with the subject. In the case of this portrait of my dear friend Claire, that chemistry is in the gift of perspective that comes from really listening to another human being and involves hours spent re-conceiving the world through each other’s eyes.

Populate the background.

The space surrounding the likeness can be just as telling about the subject as the likeness itself. With this portrait, for example, a viewer who does not know the sitter could still connect with his trumpet or even with his hat.

Create an allegorical portrait.

Allegorical portraits are a combination of the likeness of a specific person with the attributes of a mythical character. In the case of This Looks Like a Job for a Chicano! a Mexican-American man has merged with Superman to become a new kind of hero.

Group portraits together with themes.

Portraits on their own often look like the one above: appealing enough, but not exactly gripping. That said, interesting things start to happen when this same painting is put in the context of several others with similar origins. Suddenly, the portrait of a man I met online becomes a body of work about the power dynamics present in the traditional heterosexual relationship roles. Learn more about making art in series in this video!