Herbert Block (aka Herblock) was one of the most famous political cartoonists of the 20th Century. For almost seven decades his caricatures of political events and public figures graced the Washington Post, earning him a Pulitzer Prize, a spot on Richard Nixon’s Enemies List, and many other accolades. He’s most famous today for helping coin the term “McCarthyism” to describe the Red Scare, and for his endless series of cartoons lampooning Richard Nixon from the ’50s through his retirement and beyond. But he mocked and commented upon a wide variety of issues, including one sadly relevant this week as ever: gun control.

After John F. Kennedy was assassinated in 1963 by Lee Harvey Oswald, it was much noted that he ordered his rifle through a mail-order catalogue. After some politicians (including Kennedy’s brothers Bobby and Ted) proposed closing the loophole, a backlash began to develop among the right. The National Rifle Association, still ostensibly an apolitical sportsman’s association, led the counterargument by accusing the Kennedys and others of pushing the “Communist line.” Herblock, who considered gun violence “the American plague,” was not amused and published this cartoon in late 1963:

While also mocking, a few years later, the growing resistance to gun control bills starting to work their way through Congress:

As the 1960s tensions escalated into frequent race riots and antiwar demonstrations, appeals to gun ownership escalated. The American Rifleman, the NRA’s house publication, urged white Americans to stockpile weapons for self-defense and regularly ran a column highlighting vigilantes who used their weapons to gun down suspected criminals. In turn, Black militant groups and fringe leftists began buying their own firearms in efforts at self-defense. This earned the notice of many commentators like Garry Wills, who noted bleakly that his fellow Americans were “arming for Armageddon.”

In 1966, after Charles Whitman’s mass shooting at the University of Texas, arguments over gun control began to escalate again, with the NRA and its supporters in Congress shutting down several bills designed to curb gun sales. Herblock again commented on the madness of a system that resisted calls to regulate firearms even as violence and political tensions escalated.

In 1968 the gun control problem seemed even more urgent after the twin assassinations of Martin Luther King Jr. and Robert Kennedy. Connecticut Senator Thomas Dodd, hardly an extreme liberal, navigated the Gun Control Act of 1968 to the floor of Congress calling for restrictions on gun sales. While the NRA pressured senators to oppose Dodd’s bill, the hobbyist magazine Guns & Ammo decried Dodd and his supporters as “criminal-coddling do-gooders, borderline psychotics, as well as Communists and leftists who want to lead us into the one-world welfare state.”

Herblock viewed the legislation as “a watered-down version” of earlier proposals to restrict firearm sales. He directly attacked those who opposed such bills for perpetrating political violence; in one cartoon, entitled “The Vote to Kill,” he simply listed the names of each Senator who voted against Dodd’s legislation.

Nor did the arguments cease after Dodd’s bill was passed in October 1968, a few weeks before Nixon’s election as President:

Gun control did not cease to be a significant issue after the 1960s, of course. Throughout the 1980s and 1990s, as the NRA and its allies became ever more militant in opposing even the most limited gun controls, Herblock chronicled their reflexive opposition even to modest gun restrictions with a mixture of sorrow, anger and disgust.

By the 1990s it was clear that under Wayne La Pierre, the NRA would oppose even modest gun control legislation like the Brady Bill, which instituted background checks on purchasers of handguns, and the Assault Weapons Ban. Nothing – not assassinations, deaths of police officers or mass shootings in schools – would change their minds. “Countries that some call banana republics have better records than [the United States],” Herblock commented. “But then they don’t have powerful, well-heeled gun lobbies that contribute millions to political candidates and are eager to push gun sales into as many hands as possible.”

Note: These cartoons are collected on The Library of Congress and the Herblock Foundation. Herblock’s comments come from his memoir, Herblock: A Cartoonist’s Life (1993).