David Freedlander is a veteran New York City-based journalist. He writes long-form features about politics  and the arts, people and ideas, and has appeared in New York Magazine, Bloomberg, Rolling Stone, ArtNews, The Daily Beast, Newsweek and a host of other publications.

My 3,000 Paintings of President Obama: Inside Rob Pruitt’s Epic Painting Project

My 3,000 Paintings of President Obama: Inside Rob Pruitt’s Epic Painting Project

Published December 14, 2016 in 

Rob Pruitt was home watching MSNBC on election night when it became clear that the results were not going to go as he imagined they would.

Bleary-eyed the next morning he read the newspaper, scanned the Internet, and promptly cancelled a long-planned gallery show slated to open the following week.

Pruitt is a New York-based conceptual artist who The New York Times has called “one of the art world’s most popular provocateurs over the last 15 years” and someone who has developed a reputation for a certain kind of creative insouciance, from turning the Los Angeles Museum of Contemporary Art’s annual gala into an homage to marijuana (“in other words, it was one weird night” the Los Angeles Times declared in its write-up of the evening) to giving a book signing in the nude while holding onto a strategically-placed stuffed panda.

The gallery show he had planned for Gavin Brown Enterprise in downtown Manhattan was one that he began on Instagram, and that paired celebrities with their art-world lookalikes, such as Pruitt himself to Mark Ruffalo, or Jeff Koons and Mister Rogers, or John Baldessari and Papa Smurf.

But after Trump was crowned president-elect, “it was clear that the tone was going to be all wrong. We were resolutely in a new world. My show was light-hearted and frothy and more in keeping with the holiday season of spirits and good cheer. It wasn’t about re-grouping and planning what we are going to do oppose a president who ran a campaign based on hatred.”

And so that morning after the election, Pruitt made an emergency decision to stash the Instagram art and instead to re-hang in the gallery a project he had been working on for nearly eight years, and that had only seen the light of day once.

“The Obama Paintings” consists now of nearly 3,000 paintings of the commander-in-chief, one for each day of the Obama presidency. Pruitt has done one every morning for nearly the past eight years, beginning on Inauguration Day and continuing through this morning. Just after arriving at his Harlem studio, Pruitt opens his laptop and scans the previous day’s news for arresting images of the president. Each 2’x2’ painting is washed in a patriotic blue to red color scheme that Pruitt achieves by a spray gunning, much like in the same way that one would paint a car.

The show, on view through Saturday, is mesmerizing. It is as if the Associated Press hired Andy Warhol to be its chief White House photographer. Everywhere you turn in the gallery, and stacked on shelves too, is Obama, day-by-day, events of world-historical importance hard against whatever silliness the leader of the free world has to perform on any given day.

A painting of the president shaking hands with Benjamin Netanyahu is next to a painting of the president congratulating a college basketball team is next to the president exhorting a campaign crowd from the podium is next to the president playing with his dogs on the White House lawn. The show straddles a line between art and documentary. It reads like the x-ray of an obsession.

When the work was shown at the Museum of Contemporary Art Detroit in the spring of 2015, it was well-reviewed, but this time around the paintings have an added elegiac poignancy, standing as a document to an era soon to be obliterated. The New York Times called the show “gut-wrenching” and Jerry Saltz, art critic for New York Magazine called “The Obama Paintings” “The saddest show in town [and] the most joyous show in town” and named it the best art show of the year.

Pruitt, 52, grew up in suburb of Washington, D.C., going to a school where the teachers were called by their first names, where the principal rode a motorcycle and occasionally showed up barefoot, and where the students wore t-shirts that said “IALAC” for “I Am Loved And Capable.”

In Obama, he says, he saw the first president who embodied the values he grew up with.

“We were finally seeing a president who represented the entire country after 200-plus years of white male leadership. Even just that simple idea was stunning and long overdue and worth celebrating, not the mentioned that the agenda that he ran on was exactly something I could align myself with and support,” Pruitt said during a phone interview.

“There was so much excitement around his election, and so many of my friends in the New York art scene were involved in fundraising or organizing buses to the suburbs of Pennsylvania to rally voters, and it was terribly exciting and I just thought after the election, rather than just putting that energy to rest I will channel it into something tangible.”

He described the project as his daily meditation, something he spent 30-40 minutes on each morning before getting down to his real work.

"I can't dedicate myself to going to the gym every day, but I can get my mind to accomplish something in the studio,” Pruitt said. “When you look at the history of the work over the past eight years, it is really just a part of everything that's my vision. Even if I am tired of it, I am really going to miss it.”

The “emergency” decision to re-hang the work comes as the art and culture worlds have struggled with ways to counter the new president or even to imagine that their work still has relevance.

"We in the cultural sector have failed to adequately address the feelings of frustration that people of many nationalities—including, as yesterday made clear, many Americans—harbor with their societal structures,” the Berlin-based artist Olafur Eliasson wrote on Instagram the day after the election. “I lay in bed in grief and confusion. I was not merely ‘sad.’ I was derailed. All my work suddenly seemed pointless,” the novelist Teju Cole wrote of his experience of waking up on the morning of the election result.

Pruitt points the way forward, or a way forward at least. The show is a reminder that remembrance can be a form of resistance, too.

“For eight years everyone was under the impression that we were operating under the feeling that this person who at the helm of the ship was very intelligent, and made decisions that were considered, and made us feel like everything was going to be ok. So we could move forward with art that didn’t have the same kind of consciousness, that was more formal and abstract,” he said. “Now there is a new necessity, I think. Artists are communicators. When you sense that your liberties might be encroached up or eliminated there is impetus to speak up and address your peers. That is where we are now.”

As to his own plans, his own epic at an end, Pruitt says, "I don't know what I'll do next. For many of us whose day-to-day work is project-based it is always bittersweet with a sense of pride and nostalgia that it is behind you. I am not such a machine that I will immediately start with another project in the world, but I welcome the opportunity to see what comes next.”

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