John Kascht on His Visual Study of Conan O'Brien

Is Conan O’Brien a comic genius or an overrated dork? A visionary of emerging media formats or basic-cable hack? Argue all you want—I don’t care one way or the other. He has a great face and in my book (a sketchbook) that’s enough.

I’ve been drawing, painting, and sculpting Conan on and off for 18 months, ever since he agreed to be the model for a new Smithsonian film, Funny Bones: Anatomy of a Celebrity Caricature, about my caricature work. I’ve rendered him in pencil, watercolor, clay and even Cheetos. Also in marshmallows, matches, and breast-pocket hankies. I’ve scorched him into toast, too.

When you get intimate with someone’s every freckle and follicle, you learn a bit about the person underneath the features and—no surprise here—Conan is much more dimensional than the orange cartoon we see on television.

His outward appearance itself hints at his complexity. Offstage especially, without the flattening effects of makeup and studio light, his face is an incongruous assemblage of highlights, shadows, shapes, and angles. It’s perfectly emblematic of his personality—after all, the same guy who brought us The Masturbating Bear is a magna cum laude Harvard grad with degrees in history and literature. Conversation with Conan segues effortlessly from Homer Simpson to Homer’s Odyssey, from cheesy '70s TV to Elizabethan costumes; from Abe Lincoln’s use of language (Conan lectured on Lincoln at a history conference at Ford’s Theater in Washington) to bare-knuckle boxing to the minutiae of bygone elections.

As the face suggests, he’s multifaceted.

There’s a hyperactive brain under the orange hair and it parses every situation for material. As I sketched in his office one afternoon, Conan improvised a riff about what a disaster I’d be as an eyewitness to a crime. He imagined me giving an insane description to the cops, leading to the official bulletin: “Police are looking for a suspect with tiny ankles and a nine-foot pompadour!”

His instinct for deconstructing and exaggerating whatever’s in front of him is something I recognize very well. In his way, Conan caricatures.

But his favorite subject for satire is himself, and he does it with brutal self-awareness and a caricaturist’s understanding of his own appearance. Conan has reworked the raw material he was born with for maximum effect. A gravity-defying hairstyle adds 5 inches to his already impressive 6’4” height. Tailored suits and narrow pants make him seem taller still. The dark colors he favors turn his Irish complexion several shades lighter in contrast. The pale head and torch of hair appear to float high above the ground.

He frequently jokes about his insecurities and you know that it isn’t all shtick. Whether promenading in skin-tight jeggings like a deranged ostrich, or channeling his inner nerd while interviewing an actress in a low-cut dress, Conan is at his best when his physical comedy rubs up against his existential discomfort. He’s turned the body that he admits once embarrassed him into his most reliable comic—and, perhaps, therapeutic—device.

From where I sit—at a drawing board—Conan is one of the most fascinating people around, and a truly great subject for caricature. Especially since so much of the work is done before I ever put pencil to paper.