'Making Faces,' a career-spanning exhibition of the portrait artist's celebrity caricatures, opens Saturday at the Billy Ireland Cartoon Library

John Kascht began freelancing for publications when he was 14, and in the ensuing years, the artist has amassed thousands of portraits. But one public figure has reappeared more than any other: former New York City mayor and current Donald Trump attorney Rudy Giuliani.

“He's a fascinating case study. He has all these expressions where he completely transforms, and the weird thing I discovered about his face is that it’s concave, kind of collapsing in on itself, but it can also do this,” Kascht said, pointing to a bug-eyed depiction of Giuliani hanging on the wall at the Billy Ireland Cartoon Library & Museum, where the artist’s traveling exhibit, “Making Faces,” opens on Saturday, Feb. 15. “He’s like a balloon and a collapsing black hole at the same time.”

In one portrait of Giuliani, his trademark chin is enormous, and in another it practically disappears. “When you're drawing something, people tend to think that you either get a likeness or you don't — like it's a single thing. But you can exaggerate a chin or minimize it, and it still works. So there’s something very mysterious and elastic about the concept of recognizability,” Kascht said. “If it's carefully observed and well done, a really successful caricature can suggest far more than it shows. It's greater than the sum of its parts.”

For Kascht (pronounced “cashed”), a drawing begins long before he starts sketching. Observation is the most crucial part. “It's about ingesting, digesting and regurgitating,” he said. “People think about caricature as a type of cartooning. They encounter it at birthday parties or at the beach or theme parks. That's one type of expression. But it really is a form of portraiture. Like anything, it can be done well or poorly, and the quality of the final likeness has to do with the quality of the observation. … Drawing is seeing.”

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Most of the time, Kascht’s research involves looking through as many photos of a person as he can, and selecting certain ones that provide specific insights on facial features and head shape. For one series of portraits in “Making Faces,” though, Kascht was able to supplement his research with the real-life subject. The artist spent 18 months studying Conan O’Brien from afar and observing the late-night host in his everyday life, all of which is documented in a fascinating short film commissioned by the National Portrait Gallery titled “Funny Bones.” The project became an obsession for Kascht, and by the end of it, he had hundreds of portraits of O’Brien, including pencil drawings, a clay sculpture, an emoticon version and even an imprint of Conan’s face burned onto a piece of toast.

Spending so much time studying public figures has given Kascht a unique window into the lives of celebrities. It’s a world he has no desire to enter himself, and he has compassion for those who end up there. “Fame comes with a lot of suffering,” he said. “Think about never being able to leave your house without being recognized. That would feed your ego for a while, and after a time it would become deranging. … You can't live in the middle of it and not be deformed by it.”

These days, Kascht is taking a step back from the deadline-driven work that has characterized most of his assignments for the past three decades, and that’s partially due to the way the journalism industry is changing. “Some of these [portraits in ‘Making Faces’] were highly creative collaborations where I'd get the story from the writer — an intelligent piece — and I would talk to the writer about what that person's thoughts were. I could talk to the art director, who actually had the trust of an editor to make creative decisions. That doesn't exist anymore,” Kascht said. “Now it’s, ‘We need Billie Eilish by tomorrow and don't use yellow because the editor doesn't like yellow.'" 

Jumping off the deadline treadmill has allowed Kascht to make time for other projects; he’s working on a book and rediscovering a love of sculpture. “I'm taking all of this stuff I've learned about faces and people and trying to bring out some of these nuances of character in clay,” he said. “I'm just on fire again, reconnecting with how I felt as a kid making stuff.”

But looking at the dozens of portraits on the walls at the Billy, Kascht is proud of his caricatures, and "Making Faces" is a way to honor that body of work. “I didn't want this to just be a show of my greatest hits. I wanted it to be a show that peered behind the scenes a little bit and really dove into the art of caricature,” he said. “If people want to come and just laugh at images of pop culture figures, they can. But anyone who wants to tap in deeper, it’s there.”