The point of a caricature is to capture the essence of a person through exaggeration. It’s a neat trick. Too often a caricaturist errs on one side or the other of the equation, either its all exaggeration, and the person and the real personality is overwhelmed, or it is too much of a portrait, and the person’s essence is submerged. I don't know enough to provide a good history of caricatures or caricaturists, but the growth of the art is clearly connected to the rise of mass circulation magazines and newspapers in the 19th century, and can be separated from the cartoon in that a caricature generally doesn’t have a caption or an accompanying joke, but the image itself needs to be clever and amusing. If Daumier, who I confess might be my favorite French artist of the 19th century, all of your Delacroixs, Manets, and Seurats notwithstanding, the great master of the early 20th century was Max Beerbohm. ( Beerbohm was also probably the most gifted parodist in the English language, and my Christmas reading this year was Beerbohm’s A Christmas Garland, his famous collection of parodies of English writers c. 1912—the one parodying Henry James late, circumlocutionary style is perhaps the best—and my edition was illustrated by about 25 of his wonderful caricatures. And Beerbohm reminds us that a good caricature is a visual parody of someone’s face and personality.)
For those of us growing up in New York City in the 1960s and 1970s, there were only two caricaturists; Al Hirschfeld, whose illustrations, primarily of theater people, adorned the Arts and Leisure section of the NY Times for decades, and David Levine, the caricaturist in residence for the New York Review of Books, and whose images covered an astonishing range of people in cultural and politics, from the golden age of Aeschylus and Euripides to the bronze age of George W. Bush. Well, of course I liked Hirschfeld, and counted Ninas with the best of them, but compared to Levine, his caricatures were often superficial, capturing and exaggerating visual aspects of his subjects faces, without providing a deeper sense of who they were. Levine’s were different, with their huge heads and noses, and always seemed to be a commentary on the person in question. He is perhaps best remembered for his political caricatures, though he probably was best in his depictions of literary and artistic folk. And even when he was political, as in the famous one of Lyndon Johnson showing off his scar, but even in this image, the point was as much about Johnson’s personality, and his all-encompassing egocentrism and self-centered personality, as about the war in Vietnam. Levine could at times be mean, but he was never nasty. Now, a few years after Hirschfeld departed at the age of 100, Levine has left us as well. We might imagine what Levine’s Obama, or Palin might have looked like, but we will never know. The NYRB hasn’t been the same since Levine’s caricatures stopped appearing, and it will be further diminished.
You need not wonder what Levine's Obama might look like as he drew him in 2006 and it is included in his last book, American Presidents (Fantagraphics, 2008).
I would also urge you to look again at Hirschfeld's work which is not as superficial as you claim. He captured the characters that performers were presenting as written by the playwrights. He did a few lines, what many writers take volumes to say.
Both artists were wonderful, and together they present almost every significant personality of the 20th century and beyond (and in David's case, before.)
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