The comedy that got
inside Trump’s head

Wanda Sykes, who has lampooned presidencies across several decades, says President Trump hasn’t proved to be the easiest comedic target.

“You would think, ‘Oh, boy, there’s so much to make fun of,’ but really I can’t write anything funnier or more ridiculous than what Trump actually says,” Sykes told NPR’s Terry Gross last year, shortly after the debut of her Netflix standup special “Not Normal.”

“It’s like doing a parody of a parody,” Sykes noted moments later, spotlighting the conundrum of comedians trying to ridicule a president whose rhetorical style and attacks are often high hyperbole, rooted not in Oval Office tradition but in the ways of reality-show hosts, carnival barkers and open-mic insult comics. When the bully-pulpit performance leans into the extremes of a cartoon, they say, what’s a humorist to do?

Well, one constant about comedians is that eventually, they find a way. As they hold up a mirror to truth, to reflect a leader’s weaknesses, there’s always a comic angle to discover.

So who has managed to be best and do it better for the past four years — including this dire 2020, when some are finding it awfully tough to laugh?

With Election Day fast approaching, The Washington Post asked dozens of top comedy minds to tell us which standups and social media stars — and which authors and impersonators and political artists — they turn to in these times and applaud.

Here are the top picks:

Best social media satire

Sarah Cooper’s lip-sync videos

Cooper became a breakout star after her young nephews introduced her to TikTok, where this past spring she began posting short videos of herself lip-syncing to Trump’s public pronouncements under such titles as “How to Medical” and “How to Mask.” Soon she was racking up tens of millions of views; now, she’s got a Netflix comedy special and a CBS series in the works.

The Maryland-sprung comedian employs a precise range of expressions, including confidently pursed lips and desperate sidelong glances, to dramatize and undercut Trump’s speech. Cooper “reveals him and his grift so perfectly,” says Keith Knight, the “Knight Life” cartoonist and co-creator of Hulu’s “Woke.”

Actor-comedian Patton Oswalt says “she’s doing the best thing that parody and satire do, which is embracing this thing to the point of strangulation. She’s playing a character that’s almost trying to make Trump look better and, in trying to bring dignity and gravitas to his sayings, really highlights how ridiculous and damaged they are.

“That’s what she so instinctually gets about comedy — is that it’s played with a straight face,” Oswalt says of Cooper’s Trump. “This is a guy absolutely bluffing who is just empty and frightened inside.”

To watch, click here

Best standup bit

John Mulaney’s “Horse in a hospital,” from “Kid Gorgeous at Radio City” on Netflix

Mulaney is not known as a political comic, yet a single presidential joke of his has reverberated, premised on the absurd imagery of equine chaos.

“This guy being the president, it’s like there’s a horse loose in a hospital,” Mulaney says in setting up the roughly six-minute bit from 2018. “I think eventually everything’s going to be okay, but I have no idea what’s going to happen next. And neither do any of you, and neither do your parents, because there’s a horse loose in the hospital!”

Adam McKay, writer-director of “Vice” and “The Big Short,” says that Mulaney’s take is the “best bit of Trump comedy, hands down.”

“It nails perfectly how hard it is to even grasp the reality that Trump is president, let alone police or understand his decisions,” he says. “If I’m really being honest, I still don’t think I’ve processed it. I’m still getting over sane adults looking me in the eye and sincerely supporting ‘W.’ Bush in the 2000s. But that was an owl in a shopping mall compared to Trump.”

To watch, click here

(Other favorites: Wanda Sykes on the surreal American landscape in her special “Not Normal”; Katt Williams on Trump’s tactics in his special “Great America”; Hasan Minhaj on Washington hypocrisy and representation in his 2017 White House correspondents’ dinner routine.)

Best impersonation

J-L Cauvin

While Alec Baldwin stepped into SNL’s showy platform, Cauvin, a Georgetown Law grad turned New York-based road comic, spent this administration trying to get career traction with his Trump impersonation. It wasn’t until 2020, though, that he went seriously viral — with a two-minute clip that has received more than 2.5 million views on YouTube and 6.9 million on Twitter as it mocks Trump’s pandemic-recovery confidence. (Sound bite: “I’m going to fire Fauci probably on Good Friday, and call it Great Friday for Trump.”)

Cauvin’s messianic, MAGA cap-wearing character has insulted Vice President Pence and infectious-disease expert Anthony S. Fauci. His shambolic monologues spoof Trump’s off-the-cuff style, and one refers to covid-19 as a profit opportunity, calling it “the invisible enemy, trademark pending.”

Garry Trudeau, the “Doonesbury” creator, says Cauvin is “doing the most spot-on [political] impersonation since Tina Fey’s definitive [Sarah] Palin,” referring to how the SNL veteran uncannily embodied the 2008 vice-presidential nominee.

To watch, click here

(Other favorites: Anthony Atamanuik on Comedy Central’s “The President Show” barking orders as a short-fused leader; Jeff Bergman on Showtime’s “Our Cartoon President” nailing a tone of melodic overconfidence.)

Best cover artist

Barry Blitt for the New Yorker

Blitt, a Pulitzer winner this year, is a veteran watercolor-and-ink master of New Yorker covers that blend deceptive lightness and textured satiric bite. His art of the Obamas as militant leaders (“Fistbump”) went viral a dozen years ago, but in Trump, he has found a consistent go-to target. Blitt’s memorable covers include depicting Trump as a Chaplinesque clown, clumsily stuck in the gears of political machinery (nodding to the iconic “Modern Times” scene) and, in May, portraying the president as a surgeon, given Trump’s tendency to tout his medical knowledge during the pandemic.

“The best way to handle a bully is to not get roiled by them — in fact, going high and staying cool drives bullies crazy. That’s part of the secret power behind Blitt’s scathing caricaturing of Trump,” says Pulitzer-winning “Politico” cartoonist Matt Wuerker. “Instead of going low with more mudslinging, Barry lobs back with coolly sophisticated wit — the pitch-perfect retort to all the unhinged bile and bluster that’s been blasting out of Trump’s White House for four years now.”

(Other favorites: Brian Stauffer’s New Yorker cover “Under Control,” depicting Trump wearing a medical mask as blindfold; Edel Rodriguez’s bright Time covers rendering Trump’s face as a match head or as literally melting down.)

Best running late-night segment

Amber Ruffin’s appearances on NBC’s “Late Night With Seth Meyers”

Ruffin joined “Late Night With Seth Meyers” in 2014 — becoming one of the relatively few Black women to write for a major American late-night talk show — and her popular segments include “Jokes Seth Can’t Tell” and “Amber’s Minute of Fury.”

Throughout the pandemic, her segments have especially hit their mark, including in August, after Trump tweeted that he has “done more for WOMEN than just about any President in HISTORY!”

“He didn’t say he’s done good things for women,” a grinning Ruffin said. “He just said no president has done more. And he’s right — no president has done more for women, to make our lives worse.”

In response to questions from Meyers, Ruffin plays up the incongruity of making the damning political point with a perky, singsong “he did this” delivery. As “Conan” writer and standup Laurie Kilmartin says: “Amber Ruffin makes me dance to my own demise.”

She has been such a breakout that “The Amber Ruffin Show” has just landed on Peacock, the new streaming service.

To watch, click here

(Other favorites: “Last Week Tonight With John Oliver’s” Catheter Cowboy ads, bought to appear on Fox News, in which a faux spokesman explains basic concepts to Trump; “The Daily Show With Trevor Noah’s” recurring look at Trump’s circle, “Profiles in Tremendousness”; Melissa McCarthy’s SNL impersonation of White House press secretary Sean Spicer lashing out at the media.)

Best musical parody

Randy Rainbow

Six years after first going viral with his 2010 video “Randy Rainbow Is Dating Mel Gibson,” the singer-comedian launched into political music parody, spinning tunes from classic musicals into such whimsically delivered performances as “A Spoonful of Clorox” (riffing off “Mary Poppins” to nearly 7 million views on his YouTube channel), “Fact Checker, Fact Checker” (spoofing “Matchmaker, Matchmaker” from “Fiddler on the Roof”) and “Kamala!” (yes, “Camelot”). He croons on “That Don!” (a parody of “Gaston” from “Beauty and the Beast”): “His crimes are fine / The laws are jokes / His lies are all true / And the truth is a hoax.”

“Randy is basically a flamethrower,” Oswalt says. “He does it with so much of a smile — and he’s clearly having so much fun — that it’s hard to write him off as: ‘Oh, you’re just being angry’ or ‘You’re just a hater.’ ”

To watch, click here

Best fictional Twitter feed

@DonaeldUnready

Trump has spawned a slew of parody social media accounts. But one has reigned above others. Since 2017, the Twitter account Donaeld the Unready has spun out highhanded royal pronouncements by the persona of “the best medieval King out there” who aims to “Make Mercia Great Again.”

The parody feed is by an anonymous, pun-loving British archaeologist who — armed with “a slight background in early medieval history” — reacted comedically upon thinking that Trump was “talking political discourse back to the Dark Ages.” “Other people all over the world joined in, creating their own characters from the world of Donaeld,” the creator tells The Post via email. “Somehow it’s carried on. Mind you, there’s been no shortage of material.”

With nearly 90,000 followers, this Donaeld plays off real headlines. After the Atlantic reported on Trump’s comments about military sacrifice, the account referred to “losers who couldn’t even survive a battle with the Welsh.” When Trump defended the testing of his mental and physical health months after an unplanned Walter Reed hospital visit, the fake king tweeted: “It never will end, my reign, now the FALSE CHRONICLERS are scribing that your favourite King, me, was taken to the Spital of St Aiden Yourself for tests. TOTAL LIES and anyway those monks hadn’t never seen such test results. WOW.”

“The Simpsons” writer Dan Greaney says Donaeld the Unready is among the very few comedic Twitter feeds “that have given me any comfort in this nightmare.”

Best political cartoonists

Pia Guerra and Darrin Bell

Guerra was best known as a graphic novelist (“Y: The Last Man”) until Trump was elected, sparking her single-panel takedowns rendered in her stark, poignant style. She combines dead-on facial expressions with sometimes wordless satiric strikes, such as when her Trump sits on a desk and clings to the American flag as the novel coronavirus rises around him.

“Pia was already a great cartoonist,” Matt Bors, who publishes Guerra’s work on the website the Nib, told The Post last year, “and with her shift into political work, [she] instantly became one of the top editorial cartoonists in the field.”

In 2019, Pulitzer jurors named Bell the first Black cartoonist to win the prize, calling his work “beautiful and daring” in highlighting “lies, hypocrisy and fraud in the political turmoil surrounding the Trump administration.” Bell, also the creator of the strip “Candorville,” blends a painterly style with sharp visual punchlines, such as an altered bird logo for the “Jim Crow Postal Service” to lampoon claims of attempted voter suppression through delayed mail-in balloting.

(Other favorites: Garry Trudeau, whose “Doonesbury” has had arguably the best Trump satire for more than three decades, and has escalated the mockery; Michael de Adder, who lost a contract over his fine-lined Trump art; Rob Rogers, fired by the Pittsburgh Post-Gazette over his cartoon barbs; and The Post’s Ann Telnaes, whose watercolor caricatures of Trump are widely praised.)

Best satirical novel

Christopher Buckley

Much literary political satire has underwhelmed in the Trump era, writes Post fiction critic Ron Charles, but one author has recently delivered in fine form: Christopher Buckley.

The “Thank You for Smoking” author’s new novel, “Make Russia Great Again: A Novel,” is narrated by a former Trump resort hospitality worker who, out of loyalty, suddenly finds himself smack at the center of the White House. The Thurber Prize-winning author’s book, Charles writes, is “an outrageously funny novel equal to the absurdity roiling Washington.”

Buckley is humble about his humor, recently telling C-SPAN, “A satirist is like a dog chasing a car. He rarely catches up with it. … I would make no claim that my book is any more real than what’s going on. It’s my attempt at rendering it through a different lens."

And when asked whether people want humor in this harrowing time of police protests, a pandemic and the polarizing presidential election, the author replied: “Laughter is a coping mechanism.”

Send in the comedians, indeed.

Share your own picks in the comments below.

Read more

How Barry Blitt became the New Yorker’s top political cover artist

The Trayvon Martin tragedy led to Darrin Bell’s historic Pulitzer

How Pia Guerra became one of the Trump era’s most moving political cartoonists

As Joe Biden exited the vice presidency in 2016, comedy bid farewell to a one-man gold mine

Editing by Zachary Pincus-Roth. Photo editing by Monique Woo. Copy editing by Paula Kelso. Design by Beth Broadwater.