A definitive ranking of President Trump's disastrous portraits

We need to talk about these wacko portraits of Trump

President Trump.
(Image credit: Illustrated | ChamilleWhite/iStock, MichaelJay/iStock, Wikimedia Commons)

President Trump is quite taken with his own visage.

Over the years, the president has spent tens of thousands of dollars to purchase photographs and paintings of himself. The resulting gallery of Trump portraits range from the odd and tolerable to hilarious train wrecks of fantasy, patriotism, and badly drawn blond hair.

Here is our definitive ranking of Trump portraiture, from fine to terrible.

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11. A mostly normal painting

Who made it: Everett Raymond Kinstler

Where is it: Unknown — in Trump's possession

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Everett Raymond Kinstler is an actual portrait artist who has painted every president going back to Gerald Ford. Trump commissioned his portrait from Kinstler before the 2016 presidential election, and the result is impressively not bad!

Kinstler produced a perfectly likable and accurate picture of the would-be president. Applause to Kinstler for literally doing his job.

10. The official White House portrait

Who made it: Shealah Craighead

Where is it: Approximately 9,600 federal buildings and offices

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At first glance, Trump's official White House photograph looks like your standard presidential portrait. Trump appears as a normal adult man wearing a suit, a spangled blue tie, an American flag pin, and an easy smile. While the photo is closer-cropped to Trump than Barack Obama's official portrait was, it is still your standard oh-you-caught-me-standing-in-some-anonymous-corner-of-the-White-House pose.

The more you look, though, the more you might find yourself unnerved by Trump's stare. In a fascinating breakdown of the portrait's lighting, PetaPixel points out that the use of a low catchlight in Trump's portrait — reflected as white spots in the lower right corner of his eyes — "usually suggests something rather negative about the subject: that they are sinister, to be feared, or not to be trusted." That is in contrast to Pence's official portrait, where the catchlight is much more traditionally positioned.

9. The placeholder for the official White House portrait

Who made it: Uncredited

Where is it: Used temporarily in government offices until an official portrait was released more than nine months after Trump took office

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In this initial photograph, released after the inauguration, Trump scowls at the camera while posing in front of what is obviously a green screen. "I've not seen anything anywhere with any presidency that's looked like this before," University of Tennessee-Knoxville photojournalism professor Michael Martinez told Vox.

Trump's background, out of focus, is awash in an eerie blue light. Trump awkwardly hunches toward the camera, with the hair on the left side of his head unattended and frizzled.

The photo shares the same aggressive low catchlight as Trump's later portrait, giving the president an intimidating and unfriendly look. It's a weird portrait, and one that went mercifully uncredited by the White House.

8. The $10,000 portrait

Who made it: Havi Schanz

Where is it: Trump National Doral Miami

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Trump bought this four-foot painting during an auction at Mar-a-Lago in 2014 for $10,000, using charity money. He would go on to hang the portrait in the sports bar of his golf club in Miami, where it stares down anyone checking the "maximum occupancy" sign next to it.

Although it is hard to tell from photos, Schanz's painting of Trump is laid over an architectural rendering, with some of the lines showing through Trump's signature "I'm a hot-shot businessman" expression. While the image certainly glorifies the looks of Trump — it wouldn't be out of place in a triptych with Schanz's paintings of Marilyn Monroe or Madonna — it is also clearly illustrating Trump at a much younger age, without wrinkles and with eyes that can only be described as "piercing."

7. The $20,000 portrait

Who made it: Michael Israel

Where is it: Unknown — possibly Trump National Golf Club Westchester

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Two hundred years ago, during the 2016 presidential campaign, there was a brief scandal involving candidate Donald Trump's use of charity money on goodies for himself. One such gift was a six-foot-tall portrait of Trump painted in "just five or six frenetic minutes" during a Mar-a-Lago gala in 2007 by the speed painter Michael Israel, The Washington Post's David Fahrenthold discovered. Trump bought the portrait for $20,000 with his charity's money, although people have wondered openly about how exactly something like that is being put to "a charitable use."

Quality photos of Israel's painting are hard to come by, but the final image certainly conveys the sense that it was ... well, hastily done. Trump has a rooster-like swoop of hair. The portrait isn't offensively ugly — it allegedly hung in the boardroom of his golf club in Westchester for awhile — but it doesn't quite get, well, anything right.

6. The fake Time cover

Who made it: Unknown

Where is it: Five of Trump's golf clubs — they have since been removed

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Although a framed Time magazine cover might not be your traditional "portrait," this one is — because it is entirely made up. Someone photoshopped an image of Trump onto a nonexistent 2009 Time magazine cover, and the president went on to hang the image in at least five of his clubs, from Scotland to Florida.

Trump is obviously image obsessed, so the untraditional "portrait" isn't as weird as it might seem (scratch that — it's still very weird). Still, the unknown artist behind this forgery made a rookie mistake, including two exclamation points on the cover. As The Washington Post explains, "Time headlines don't yell."

5. The requisite Jon McNaughton portrait

Who made it: Jon McNaughton

Where is it: Sean Hannity's Twitter account

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We really drop off the ledge between portraits in the sixth and fifth spots. While the Michael Israel portrait at least seems to be coming from an earnest place, the Trump administration's "unofficial artist," Jon McNaughton, makes some of the wackiest art this side of North Korea. In addition to inserting Jesus Christ into random political images, hilariously bashing former President Barack Obama, and using some of the least inspired symbolism imaginable (what if the Constitution, BUT ON FIRE?), McNaughton is a Trump supporter and makes the president the subject of much of his work.

Fox News host Sean Hannity is such a fan that he even bought the original painting of McNaughton's "The Forgotten Man," a zany picture where a bunch of disapproving presidents beg Obama — who is standing with his arms crossed on top of the U.S. Constitution, get it — to pay attention to a sad white man on a bench.

Hannity allegedly promised McNaughton that he had bought the image to give to Trump to hang in the White House — which mercifully didn't happen.

4. The Trump-approved meme

Who made it: Call of Duty

Where is it: Donald Trump Jr.'s Instagram account

View this post on InstagramThis is amazing. #fourthofjuly #4thofjuly #trump #magaA post shared by Donald Trump Jr. (@donaldjtrumpjr) on Jul 4, 2018 at 7:06pm PDT

Although there is a lot (A LOT) of extremely bad photoshopped fan art of Trump out there, the #FourthOfJuly #MAGA portrait is special because it was approved of, and shared to 1.2 million followers, by the president's son, Donald Trump Jr.

Though it looks like it was dredged up from some frog-ridden corner of 4Chan, #FourthOfJuly is actually promotional art from Call of Duty: Endowment, except in the original image it is George Washington who is holding an eagle over the smoldering remains of his enemies. "I want to hang this up in my home," one commenter said while another, awed, wrote: "Now that's a portrait."

That is debatable.

3. "The Republican Club"

Who made it: Andy Thomas

Where is it: The White House

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All portraits are a kind of fantasy, an ideal representation of a person. But portraits can also capture a kind of fantasy world, one in which Trump is slim and glowing and breaking the fourth wall with his gaze, sipping a diet Coke alongside ... Dwight Eisenhower, Abraham Lincoln, Richard Nixon (laughing jollily, with wine), and the undistinguishable face of the "first Republican woman president," to name a few.

Andy Thomas was not commissioned to paint Trump, but he told The Washington Post that he wanted to "make people as good-looking and happy as I could" in his art. The result is the kind of cheap kitsch you would find in a tourist shop (there is a Democratic version, too), less offensive than Jon McNaughton's portraits but no less insane in execution.

2. The Buff Trump

Who made it: Ralph Cowan

Where is it: Mar-a-Lago

The famous "buff Trump" portrait is one of the most disastrous attempts at capturing Trump's likeness, in part because the man depicted looks ... well, he looks nothing at all like Trump. Ralph Cowan was commissioned by Trump to paint the portrait in 1989, and said he decided on a tennis outfit over a business suit because "I wanted the 'Palm Beach' look." Sure.

But there is more going on in this portrait than just a strangely proportioned Trump. One is, of course, the pose — Trump resting his arm on a lifted leg, although what his foot might be resting on is out of sight. The other is Trump's skin tone, which is an unflattering shade of "I forgot to wear sunscreen." Then there is the background, which contains almost biblical sunbeams illuminating a rocky coast, as if at any moment Trump might sweep his dashing gaze out over his kingdom. It is magnificently bizarre.

1. Trump with an eagle

Who made it: Unknown

Where is it: The Trump campaign headquarters at Trump Tower

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Would you just look at this monstrosity. I mean really, truly look at it.

This painting was hung in Trump Tower, apparently without a sliver of irony. Again Trump has resumed his signature pinched squint into the middle distance. His face is weirdly puffy, illogically framed, and his hair looks almost globular, like a single kidney-shaped yellow entity has been plopped onto his head.

There is a screaming eagle, because of course there is. There is not one, but two American flags, with THE STARS LITERALLY FLINGING OFF. In the background, the sun rises over 'Merika, where you can almost hear the distant chant of "USA! USA!"

It is gloriously ugly. It is perfect. It is everything we deserve.

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Jeva Lange

Jeva Lange was the executive editor at TheWeek.com. She formerly served as The Week's deputy editor and culture critic. She is also a contributor to Screen Slate, and her writing has appeared in The New York Daily News, The Awl, Vice, and Gothamist, among other publications. Jeva lives in New York City. Follow her on Twitter.