Artist Jack Davis created this illustration, rendered in watercolor and ink, for a 1973 Time magazine cover. (National Portrait Gallery, Smithsonian Institution; gift of Time magazine; Estate of Jack Davis 1973)

8 cartoons that shaped our view of Watergate — and still resonate today

Herblock, Garry Trudeau, Patrick Oliphant, Paul Conrad and other artists who skewered Nixon and his inner circle made the era a boom time for political satire

11 min

Bob Woodward vividly recalls Herblock walking through the Washington Post newsroom in the ’70s, several sketched ideas in hand. The political artist would seek out Woodward, among others, for feedback — two legendary journalists considering a cartoon that the power brokers of Washington would wake to the next morning, a few sometimes finding themselves to be the butt of the visual joke.

Woodward would read each roughed-out draft. Herblock, meanwhile, would “read” Woodward — looking for his immediate response, for that moment of recognition, be it a laugh or a grin or a gasp.

“He understood the connection between a cartoon and the instant reaction,” Woodward says. “When he would come around with his four or five or six tentative ones, that’s what he was doing — but I didn’t realize that until much later.”

And to this day, Woodward can describe in detail some of Herblock’s sharpest cartoons about Watergate — a half-century after burglars connected to President Richard M. Nixon’s reelection campaign broke into the Democratic National Committee headquarters at the Watergate complex, on June 17, 1972. Woodward and Herblock would share in The Post’s 1973 Pulitzer Prize for public service for coverage of Watergate; 10 supplemental editorial cartoons were included in the entry.

Herblock — the nom-de-toon of the late Herbert Block — had long lampooned Nixon by the time the break-in occurred. So had such peers as Paul Conrad of the Los Angeles Times, Jules Feiffer of the Village Voice and Patrick Oliphant, a Denver Post star before he moved in the mid-'70s to the Washington Star.

Other gifted satirists gained fresh traction during Watergate, including Jeff MacNelly, Mike Peters and rising cartoonist Garry Trudeau, who would win a Pulitzer in 1975 for his “Doonesbury” work — the first comic strip to do so. And such brilliant editorial illustrators as Jack Davis, David Levine, Edward Sorel and Ralph Steadman crafted their exaggerated takes on Nixon, rendering him with arched back, ski-slope nose, suspicious eyebrows and heavy jowls.

“In many ways, those Watergate years were the zenith for political cartooning in America,” says Matt Wuerker, the editorial cartoonist for Politico.

Upon the break-in’s 50th anniversary, illustrations by Davis, Oliphant and Sorel are among the artworks featured in the National Portrait Gallery show “Watergate: Portraiture and Intrigue,” on view through Sept. 25.

Kate Lemay, the gallery’s acting senior historian and curator of its “Watergate” exhibit, says that although investigative journalism broke the Watergate story and uncovered the scandal’s abuses of power, “art was also in the nexus of that journalism, and I think it gets overlooked.”

To mark art’s role in the coverage, here are eight cartoons that proved to be particularly powerful during the Watergate era.

Garry Trudeau’s ‘Doonesbury’ calls Mitchell ‘guilty!’

Heading into the summer of 1973, with the nation glued to the Watergate hearings, “Doonesbury” provided a comic service by profiling some of the Watergate conspirators. On May 29, Mark Slackmeyer, the strip’s campus-radio talk jock, took on former attorney general John Mitchell, who readers are told had recently been “repeatedly linked with both the Watergate caper and its cover-up.”

Slackmeyer draws his own conclusion with a punchline that would become fixed in American culture: “That’s guilty! Guilty, guilty, guilty!!”

“The ‘Guilty’ strip caused such a furor with editors that it sealed the transgressive reputation the strip had been gaining in the preceding years,” Trudeau says now. “Mark had said something out loud — and with unfettered glee — that everyone was thinking.”

The strip “produced the pleasure of confirmation bias,” says Trudeau, yet he notes that a dozen U.S. newspapers dropped the controversial strip. Not even a fictional cartoon character could speak so freely.

Would such a bold comic make waves in the political climate of 2022? “Since social media now makes it possible for anyone to safely make such incendiary judgments,” says Trudeau, citing such phrases as “Lock her up,” “I doubt the same strip published today would cause a ripple.”

Paul Conrad’s spin on Nixon’s web of deceit

Conrad reveled in satirizing Nixon with bold imagery and minimal wording.

In one of Conrad’s cartoons from the Watergate years, Nixon is depicted as a Napoleonic figure sternly commanding a ship. In another, drawn right after the break-in, Nixon poses as a utility worker as he drills into a wall at the door of Democratic headquarters, from which an onlooker says: “He says he’s from the phone company … .”

One of Conrad’s darkest and starkest cartoons of the era was a 1973 white-on-black portrait of Nixon depicted as a web of deception — with the names of many conspirators spun in the silk of corruption and intrigue.

Lalo Alcaraz, this year’s Herblock Prize recipient, grew up in Southern California inspired by Conrad’s work: “His cartoons were so blunt and powerful [that] hard-hitting doesn't even come close. They were devastating.”

Politico’s Wuerker grew up living in the same L.A. neighborhood as Conrad, and as a teenager he watched the news with the Conrad family during Watergate, learning “new ways to swear at the TV.” Notes Wuerker: “I know despite his multiple Pulitzers, Con’s proudest accomplishment was being included on Nixon’s ‘enemies list.’ ”

Patrick Oliphant imagines a Watergate ‘bug’

What was it like to mock Nixon in real time? “He fascinated me,” Oliphant says by phone from his New Mexico home. The retired Pulitzer-winning cartoonist would follow Nixon’s Shakespearean flaws in the news and ask himself: “How could he be that way consistently?”

Oliphant was fond of drawing Nixon as furtive, such as in a cartoon in which the president whispers to a Vietnam War protester through the White House fence.

And in a work now on display at the National Portrait Gallery, Oliphant pictured Nixon and Chief of Staff H.R. Haldeman standing just around a corner as they gauge the appetite of a large “Watergate bug.” The critter has just devoured the political career of acting FBI director L. Patrick Gray, who resigned in April 1973 for his role in the Watergate conspiracy. In the cartoon, Nixon asks: “Do you think it’s still hungry … ?”

Oliphant says with a laugh that he liked to render “Nixon as a pair of eyebrows, then drop a couple of eyes in — you didn’t need anything else.”

Many cartoonists initially seize on a leader’s prominent features. Yet, “Oliphant took his caricature to another level as the president’s criminal activities during Watergate were exposed and changed him from a cartoony version to a darker and sinister figure,” says Ann Telnaes, the Pulitzer-winning political cartoonist and animator at The Post.

He even mocked the president in sculpture, including the bronze “Nixon on Horseback” — in which the president, in Napoleonic pose, looks wearied by Watergate instead of Waterloo.

Herblock renders judgment on a reeling Nixon

In 1954, Herblock viewed Vice President Nixon’s “anti-Communism campaign” as smear tactics against Democratic legislators and imagined him emerging from a sewer manhole. Two decades later, the Post cartoonist was depicting Nixon as a crook.

Within days of the Watergate break-in, the artist began his long barrage of cartoons skewering Nixon and his conspirators.

Today, Woodward praises a Herblock cartoon that has lost none of its visual impact. In November 1973, several months after the existence of a White House taping system came to public light, Nixon told 400 Associated Press managing editors during a televised Q&A: “People have got to know whether or not their president is a crook. Well, I’m not a crook.”

The following May, Herblock drew Nixon hanging perilously between two reels of tape. In his mouth is the word “not,” leaving the two tape ends in his hands to read: “I am a crook.”

Pia Guerra, the graphic novelist turned popular political cartoonist, says it’s one of her favorite Herblock works. “It says so much so simply. It communicates everything you need to know about the scandal, that his removal of those crucial moments of the tapes makes him the crook he so boisterously claimed he wasn’t. It captures his contempt and ugliness and guile. It’s a perfect cartoon.”

Edward Sorel imagines the art of the Nixon deal

Edward Sorel doesn’t mince words when reliving some of his satirical illustrations for various publications during Watergate: “Nixon was a hateful person, and any time I could do him was a pleasure.”

Sorel has caricatured a cultural parade of famous faces across more than six decades, from Hollywood to Washington to overseas. And of Nixon, the artist says: “He just had a face that was meant for caricature.”

In one of his more biting works, he imagines a heavily eyebrowed Nixon trying to explain to a wide-eyed Gerald Ford a deal whereby Ford, as future president, will pardon Nixon.

The National Portrait Gallery exhibit includes a Sorel illustration in which then-Post publisher Katharine Graham waves goodbye to John Mitchell, who would serve time for his role in the Watergate conspiracy and coverup. In the illustration, Mitchell’s body is clad in prison stripes as he is put through the wringer — a reference to a comment he had uttered to reporter Carl Bernstein. For the 1972 Post article, the quote read, “Katie Graham is gonna get caught in a big fat wringer if that’s published,” after editor Ben Bradlee judiciously altered Mitchell’s original, cruder remark.

Says the gallery’s Lemay: “It’s just kind of satisfying to see her in that position of power after he said such a disrespectful thing about her.”

Jack Davis captures the Watergate blame game

Jack Davis, master that he was, was equally at home drawing for Mad magazine and Time.

“He could be zany and cartoony in one illustration and then swing over to being more realistic and illustrative in another, and yet somehow both were unmistakably Jack,” says veteran Mad caricature artist Tom Richmond.

An iconic Davis magazine cover — rendered for Time in April 1973 beneath the headline “Watergate Breaks Wide Open,” and now in the Portrait Gallery’s exhibit — imagines a circle of conspirators ensnared in its tools of taping and surveillance, each finger-pointing at someone else. The art nods to an 1871 cartoon by Thomas Nast, who was skewering the fiscal chicanery of William “Boss” Tweed’s corrupt Tammany Hall political machine.

From 1972 to 1977, Davis illustrated 23 Time covers, including depictions of the decade’s three presidents; he had a hand in six of Time’s 55 covers showing Nixon, according to D.W. Pine, the magazine’s creative director. “I love that he once said that his Time illustrations were done with little ‘direction’ from the editors,” Pine says.

David Levine’s Nixon wants some inquiries made

Oh, the timing. David Levine, the late master caricaturist, rendered Nixon as Marlon Brando’s crime boss, Don Vito Corleone, in “The Godfather,” the month before the Watergate break-in.

“My father did have an uncanny ability to see in advance [what] everyone would eventually come to see,” says son Matthew Levine.

In the mash-up image, Don Corleone sports the low, dark brow, sloping nose and shadowed jaw of Nixon.

David Levine drew Nixon more than 80 times for publication, says his son, with the president’s eyes growing shiftier and the appearance growing more disheveled over time. “Nixon was absolutely his favorite target amongst all American presidents.”

Mike Peters shows Nixon’s White House as a castle in the sand

How much did Mike Peters enjoy waking up to Watergate headlines?

Every day in the morning paper, the Pulitzer-winning cartoonist for the Dayton Daily News found so much fertile satiric terrain. And the more Peters learned about Nixon, the more the cartoonist leaned into how “bizarre” the president seemed.

So when Nixon resigned in the summer of 1974, Peters drew him along the beach — evocative of Nixon’s “Western White House” in San Clemente, Calif. Except that the cartoon’s White House made of sand is crumbling, about to be washed away.

“For a cartoonist, Nixon looked like what Nixon actually was: a seedy, backstabbing, humorless character,” Peters says. “Just his eyebrows and those eyes peering beneath them.

“God, it was great.”

Design by Hailey Haymond. Editing by Zachary Pincus-Roth. Copy editing by Annabeth Carlson. Special thanks to Alice Crites, Warren Bernard, the Huntington Library and the Herb Block Foundation.