A Trump Portrait Contest Provides Some Artistic Catharsis

The Trump portraits that won Crooked Media’s contest: Jamie Fontana (left), Casey Promise (center), and Abigail Hammett (right) (all images courtesy the artists)

The official portraits of Barack and Michelle Obama have inspired more than just memes — they’ve inspired hope. Hope for better days, better outcomes, and, perhaps most of all, better leaders. This last sentiment is one the folks at Crooked Media really ran with, harnessing the media frenzy around the Obama portraits to put out a national call for Donald Trump portraits. Official presidential portraits are typically commissioned post-presidency, so in a sense this competition offered the anticipatory satisfaction of imagining the premature conclusion of Trump’s political career.

Like all presidents, Trump will leave behind a unique legacy, one partly defined by his unnatural skin tone, squinting eyes, and bizarre hairstyle. Those qualities clearly resonated with listeners who responded to the Lovett or Leave It podcast’s call for Trump portraits a little over a month ago. The show received more than 1,000 entries. Narrowing the field to 18 finalists took a team of experts and interns; determining the winners required the internet. Users were asked to judge the merits of the finalists, which ranged from a minimalist orange line drawing and an image of Trump’s face made entirely out of toys, to a stylized rendering of the president with a flamingo on his head.

The three winners were announced on Friday: Abigail Hammett’s subtle photographic portrait of Trump as a donut with a gently folded-over cheese slice; Jamie Fontana’s ornate narrative painting depicting the president as a child on the back of Russian President Vladimir Putin; and Casey Promise’s realistic drawing of Trump vomitting Twitter birds. In addition to fame and glory, these winners will get to see their works turned into merchandise, with proceeds from sales going to P.S. Arts, a non-profit that supports arts education in California public schools.

Submissions by Olivia Wolfe (left) and Lauren Kaelin (right) to Crooked Media’s Trump portrait contest

Perhaps just as extraordinary as the winners themselves, though, was the remarkable quality of the finalists — a surprise given that online open calls tend to attract more than their share of lackluster entries. The diversity and quality of the 18 works selected as finalists could easily warrant a show at an established New York gallery.

For example, Olivia Wolfe spent more than 10 hours working on an incredibly detailed portrait that depicts a shirtless Trump clutching his phone while in a bed covered with MacDonald’s cartons and fast food. He lies underneath an American flag held up by two twitter birds. Wolfe, however, expressed dismay that her image had been altered to fit the gilded frames of Crooked Media’s website.

“They cropped out a Hillary dartboard!” she told Hyperallergic. Wolfe said that the amount of time she spent on the project made her wonder if others had taken the contest as seriously. “Then I saw the finalists.”

A submission by Paul Fiegenschue to Crooked Media’s Trump portrait contest

Another finalist, Paul Fiegenschue, told me that he also had his image cropped, though he wasn’t overly concerned because he’d submitted a series of 24 sketches that look fairly similar. His series was produced before Trump even won the election. “He was just a terrible joke, so I was trying to pull some bit of joy out of what was going on,” Fiegenschue said. The artist based his drawings on a series of Trump piñatas that made the press rounds during the primaries. After the election, though, Fiegenschue’s production of Trump art slowed considerably. “I just kinda shut down,” he said. This was a relatively rosy take compared to other artists with whom I spoke.

“He’s this putrid oil stain on the oval office and an entirely wretched person,” artist and proud LGBTQ community member Casey Promise, one of the winners, told me over the phone. “To be honest, I don’t even remember submitting the portrait. I must have done it in a daze.”

Promise’s drawing is a hyper-realistic image of Trump vomiting tweets — a subject she says is atypical for her. (The graphite drawings on her website depict surrealist figures whose bodies have been assembled from trees, humans, and animals.) She was, however, quite clear on why she made the piece and her goals: “It would make my year if he saw it and there was a twinge of hatred for me. I would be happy as an artist.”

Submissions by Lauren Hughes (left) and Rosie O’Donnell (right) to Crooked Media’s Trump portrait contest

One gets the sense that another finalist, actress and comedian Rosie O’Donnell, shared those feelings. O’Donnell has famously sparred with Trump since 2006, when she ridiculed him on The View. Her submission, created on her smartphone, depicts a plump, red-faced Trump in a black suit. O’Donnell did not respond to Hyperallergic’s requests for comment.

Everyone has their own way of dealing with the Trump presidency; for many, one coping mechanism is to listen to Pod Save America every week. “I’m so honored to be part of this contest,” finalist and friend of the Pod, Lauren Kaelin, told Hyperallergic. For her piece, Kaelin used a widely circulated meme of Trump entering Air Force One while the wind flipped over his toupee, producing an impressionistic portrait in a style similar to Lucian Freud. She explained that her portrait on vellum was made in effort to render its subject faithfully. “I wanted to chose something that was a twist on a traditional portrait, so I used a profile shot.”

Submissions by Alex Lockwood (left) and Edward Charbonneau (right) to Crooked Media’s Trump portrait contest

Like many other finalists I spoke to, Kaelin fawned over Abigail Hammett’s winning portrait, a photograph of a glazed donut on a sidewalk that she adorned with a gently folded-over slice of cheese. This evocative still life includes a nearby cigarette butt, which adds to the grossness of the image, reducing Trump to his toxic essence. “I went and bought a donut and craft singles and threw it on the ground,” Hammett told Hyperallergic. “I styled the cheese slice a little bit and that was it. I did it on my lunch break.”

Prior to the winners’ announcement, Promise, like many of the finalists I spoke with, seemed happy just to be included. “Whomever wins, I’m in full support that,” she told me. On Saturday, she got back in touch to let me know that she and two others had won the contest. She added: “I knew they couldn’t choose just one.”