Okay, so maybe I didn’t read many of the articles in my father’s copies of Playboy during the 1960s and early 1970s. But I always read the cartoons. And I learned plenty from my favorite cartoonist, Gahan Wilson, who passed away on November 21 at the age of 89.

Wilson’s cartoons combined brilliant wit and a great bullshit detector. He aptly characterized his own work as “a positive reaction to hopelessness.” He perceived and exposed the absurdities and shams of modern existence and provoked horse laughs four times out of five.

Wilson had a knack for revealing the tawdry reality around the corner. One of my favorite cartoons shows a smiling boy behind a little stand and a homemade sign touting five cent “iced drinks.” A bulky guy with a fedora hat and coat slung over his shoulder happily chugs a glass. Just around the corner, another guy—a previous customer—is on his knees gasping, his bulging eyes staring at an impish kid behind a ramshackle stand with a sign, “Iced Drink Antidote, $1.’’ Antidotes were a lot cheaper in the 1960s.

Another classic Wilson cartoon features a psychiatrist asking a patient stretched out on his couch, “When did you first become aware of this imagined plot to get you?” while motioning to two men with long knives sneaking into the room. That sketch is a wonderful reminder that just because you’re paranoid doesn’t mean they aren’t out to get you. (Wilson did a great New Yorker cartoon of a frustrated FBI sniper team that keeps getting spotted because of their brazen FBI logos.)

Wilson’s mastery of morbidity allowed for deft jabs at military madness. One Playboy cartoon shows a shell-shocked soldier holding a bloody knife and an assault rifle, looking at complete devastation all around him and smilingly declaring, “I think I won!” Another shows a Dr. Strangelove-type scene in which a politician asks a military officer while they stand next to a table with an illuminated map: “You mean what we did just then was an actual war?” Another shows a nebbish congressman listening to a wild-eyed general: “Limited nuclear war, sir, is where people like you and I survive.”

I met Wilson 10 years ago at the Small Press Expo cartoonist show in Bethesda, Maryland. He was scheduled to give a talk, but was just then looking around, perhaps uncertain of finding the lecture room in the cavernous Marriott hotel. I walked up, mentioned that I knew where he was speaking, and chatted for a pleasant five or 10 minutes as we headed to the venue. I mentioned that he probably knew the Playboy Forum editor I had worked with for eight years, and the gist of his reply was “that’s nice.” He may have thought I was full of crap but he had the “very pleasant gentleness” that he ascribed to cartoonists as a class.

His spiel that day was far and away the highlight of the cartoonist show. When he was a youngster, his family lived in an apartment next to that of one of the Chicago Tribune editors. After he acquired a tape recording device, he started getting invited to parties and would openly tape bigwigs getting drunk and making fools of themselves. He said it was very helpful “at an early age, seeing world leaders revealing themselves to be idiots.”

Wilson recounted about how, after serving in the Air Force and graduating from the Art Institute of Chicago, he moved to Greenwich Village in the 1950s and traipsed around showing magazine staffs his cartoon portfolio. One editor laughed out loud repeatedly while looking at them, then announced, “Great cartoons, kid—but our readers wouldn’t understand them.” His New York Times obituary notes that Wilson “settled into a spartan 1950s bohemian life in New York, trying to break in but mostly accumulating rejections.” Wilson explained in 1982: “Dealing with poverty wasn’t the biggest barrier of my career. The hump was dealing with the emotional part of rejection. You have to say, ‘I will not accept it,’ and go on.”

Even after he became famous in the 1960s, he said that a lot of his cartoons never sold. He also declared: “Luck is tremendous in the freelance version of art—I’ve known lots of people who should have made it but they had lousy luck.”

Wilson thrived as an artist and respectable subversive because he paid attention to what editors wanted. During the question and answer period at that 2009 event (audio here), someone asked whether he adjusted his style or humor for different markets (Playboy, the New Yorker, National Lampoon, etc). “It is like going to a party,” Wilson replied. “It is important to know who is throwing it, what they want to talk about, who the guests will be, what they will be wearing.” He talked about changing his mindset depending on the market he was targeting: “It is all very calculating.”

I asked Wilson whether he thought editors have become more dim-witted so far as catching humor over the past 50 years. He said he didn’t think so. I muttered but asked no follow-up.

Wilson brought joy to millions for more than half a century and helped people laugh even at the valley of the shadow of death. His work and memory should be hailed by anyone who loves life despite “the slings and arrows of outrageous fortune.”

James Bovard is the author of Lost Rights, Attention Deficit Democracy, and Public Policy Hooligan. He is also a USA Today columnist. Follow him on Twitter @JimBovard.