The illustrator talks about his surprising approach to portraiture in advance of a conversation with C.F. Payne at the Billy Ireland Cartoon Library

Not long ago, illustrator Drew Friedman was scrolling through Facebook and saw that somebody had posted a drawing of Abraham Lincoln, which made Friedman realize he had never drawn his own portrait of Lincoln, one of the most recognizable faces in American history. So he drew it, posted it and then thought he’d try his hand at a few more presidents.

“I have drawn more recent presidents — George H.W. Bush, a little bit of Reagan, Clinton, George W. Bush, Obama and Trump — for magazine assignments over the years. But I had never really drawn any [president] before that,” Friedman said recently by phone from his home in northeast Pennsylvania. “So I started doing these drawings of some early presidents. Some of them, I didn't even know what they looked like. And I just realized, well, I have the makings of what might be a new book.”

Friedman kept at it, eventually drawing every U.S. president for his recently released book, All the Presidents (Fantagraphics), for a total of 44 portraits (Donald Trump is the 45th president, but 44 men have held the office; Grover Cleveland served two non-consecutive terms). And while fans of Friedman who know him from his caricature work in dozens of periodicals over the past few decades likely expected satirical depictions of these commanders in chief, Friedman revels in taking unexpected left turns. So for this project, he stuck to classic portraiture.

“My approach was to be as respectful as possible with all these people, including the current president. And I kind of struggled with that one. I saved him for last because I wasn't sure exactly how to approach him,” said Friedman, whose earliest drawings of Trump date back to the 1980s in Spy magazine. “I've actually posted that portrait on Facebook, and I get a lot of reaction, like, ‘Oh, that's perfect. It's like you're exposing his inner soul.’ And then more people have been saying, ‘Oh, my God. You should have gone so much further. You made him look too good.’ And that's kind of what I want. I don't want to slam you on the head and say, ‘This is what this portrait represents.’”

Friedman did, however, apply his signature “warts and all” approach to the portraits. Wrinkles and blemishes abound. If a president had liver spots, the portrait has liver spots. “When you look at portraits of presidents dating back to the 1800s, most of them are glamorized — especially the portraits of Washington and the earliest presidents. There's not a blemish on them. They look kind of unreal. They're just so perfect looking,” he said. “So my thinking was, well, let me try to present them as perhaps they really looked — not overly glamorized and not overly whitewashed. In my style.”

All 44 portraits are currently on display at the Billy Ireland Cartoon Library & Museum as part of “Drawn to Presidents: Portraits and Satiric Drawings by Drew Friedman,” and on Saturday, Nov. 16, Friedman will give a tour of the exhibition at 4:30 p.m., followed by an open-to-the-public conversation with illustrator C.F. Payne at 5 p.m. Many other political works by Friedman will be on display, as well, including a portrait of Obama that ran on the cover of The New Yorker after the 2009 inauguration, along with a recent portrait of Trump and David Kushner that will be featured in an upcoming episode of the Netflix series “Dirty Money.” Plus, there’s all the presidential drawings Friedman illustrated over the years for Heavy Metal, National Lampoon, MAD, Time, The New York Observer and more.

“I did several hundred covers for The New York Observer, including when Jared Kushner was publisher. I did over 50 covers for him when he was publisher,” Friedman said. “I don't know if Mr. Kushner is gonna show up at the opening. You never know.”

These days, though, Friedman tends to avoid political work. “There's so much good political caricature work that's being produced,” he said. “But there's just so much. It’s an overwhelming amount of stuff. I don't know what I could even contribute at this point.”

So don’t expect the next book to focus on vice presidents or famous senators. “It was an experiment,” Friedman said of All the Presidents. “I wanted to present the most exclusive club in the world — and probably in the history of the world — and these 44 men who belong to this club. … Some of these guys, their faces are not that interesting, but just the fact that they're part of that club makes them interesting.”