If you were to ask a portrait artist to define the most difficult type of portrait to do, the chances are that he or she would probably tell you it would be the group portrait, even though artists today seldom get called upon to do them. In dealing with a single figure, the compositional possibilities are varied but also relatively clear-cut. Aside from getting really radical, how many different ways are there to pose a single figure in a portrait? And moreover, single figures are what artists have always tended to practice upon in their art training, and that with which they are most familiar. Now, adding a second figure theoretically almost doubles the possibilities, as far as composition is concerned, yet strangely, too, also limits them in that, presumably the two figures need to relate to one another and thus they tend to become two in one. So even with two figures, there are still a fairly manageable number of possibilities.
However, just as "two's company and three's a crowd," once the group portrait really starts to become a group, with the addition of a third, or a fourth, or a fifth figure, then suddenly the thing may begin to resemble a jigsaw puzzle. Artists today have a distinct advantage over those from distant eras in that photographers, in shooting group portraits, have tended to standardize a few of the most basic formal figural arrangements; and more than that, have also standardised them in most people's minds so that what is expected of the portrait painter today is often very limited, static, and straightforward, especially in dealing with larger groups. But if painters are only satisfied to repeat what works for a photographer then, although they may satisfy the minimal requirements insofar as most customers are concerned, they end up selling short both themselves and their client. At their best, group portraits should project a degree of relaxed informality while at the same time giving some indication of the relationships of the various figures. Yet they should also maintain a pleasant, solid, interesting compositional arrangement. And, while this seems simple and logical enough to say, in practice it is exceedingly difficult. Although the artist, as a photographer (or using a photographer), has the luxury of a good deal of trial and error for very little cost and effort as compared to the portrait artists of the past (who had to sketch out all the possibilities), that's not to say working from a photo provides the total answer.
First of all, as the number of people in the painting rises, so too does the unlikelihood that any one photo is going to have an ideal likeness of all the individuals involved. Thus, at the very least, the artist must master the art of switching around heads and bodies like a Dr. Frankenstein by using perhaps several different photos. Fortunately today, the computer makes this feat relatively simple, even fun. But going beyond that, there should be interplay between the figures themselves and the viewer. Inasmuch as most group portraits today are of families, this factor becomes all the more important. Ideally the portrait should impart to the viewer some recognition of the roles and relationships of the various family members one to another. And of course, the more loosely composed the figures are, the more important becomes the background, which also plays a role in the composition. It could be a family home, or a favourite corner of the backyard, the living room, or perhaps the front steps. In any case, the setting itself often becomes, in effect, an additional figure in the painting.
Good photography, skilful photo manipulation, a keen compositional eye, and sensitivity to personal relationships are all important in a group portrait. But the artist should also have a working knowledge of the ways in which portrait masters from the past have dealt with these same problems. That means studying, and longing to match, the group portraits of Rembrandt, Hals, Velázquez, Gainsborough, Reynolds, Copley, Sargent, Degas, Renoir, Rodin, and even Picasso. Velázquez’s Las Meninas, Hals' Banquet of the Jorisdoelen Officers at Haarlem, Rembrandt's Night Watch, Copley's The Copley Family, Sargent's The Daughters of Edward Darley Boit, and Degas' The Bellelli Family are especially useful in this regard. But as important as all this is, there is still the basic, daunting task of getting a good likeness, in this case, of not one, but several, distinctly different individuals, recalling, as John Singer Sargent is said to have said, "A portrait is a painting in which there's something wrong with the mouth." Now, multiply that times three...or four...or more...