The 10 Most Interesting Paintings of US Presidents


Government buildings and presidential libraries around the country are full of official portraits of our presidents. While some of them are noteworthy, most are boring pictures painted by hacks. With President’s Day just around the corner, we dug deep to find an inventive, amusing mix of images of our leaders, both past and present. From contemporary masters Andy Warhol, Robert Rauschenberg, and Chuck Close to outsider and street artists Reverend Howard Finster and Robbie Conal, we found works that truly provide an alternative view of the White House.

Robbie Conal’s painting of Ronald Reagan is one of the most recognizable political images of the 1980s. Painted in 1988, Contra Diction references the Reagan administrations illegal funding and arming of Nicaragua’s right-wing contras fighting the leftist Sandinista regime. The painting was turned into a poster that volunteers plastered on walls across the country and around the world.

Robert Rauschenberg’s 1964 silkscreen painting, Retroactive 1, mixes a media-generated image of President Kennedy from a televised news conference with a parachuting astronaut and other found objects to create a visual overview of the times and a memorial for the recently slain leader.

John Singer Sargent’s 1903 painting of Theodore Roosevelt was the first official portrait of the president. Painted from life in countless sessions at the White House, the portrait reveals the intelligence and determination of the “Rough Riding” statesman.

Andy Warhol reportedly raised more than $40,000 for the Democratic Party with his 1972 satirical portrait of Richard Nixon with the campaign slogan “Vote McGovern.” Made to support Democratic presidential candidate George McGovern, the silkscreen piece paints Nixon is a bad light — showing the incumbent leader as a green-faced monster with a head too big for his body.

Robert Colescott turned the table on issues of race with his ironic 1975 painting George Washington Carver Crossing the Delaware. Based on Emanuel Gottlieb Leutze’s 1851 canvas Washington Crossing the Delaware, which hangs at the Metropolitan Museum of Art in New York, Colescott controversial painting depicts the African American inventor George Washington Carver leading the charge with an army of minstrel-like black characters drinking moonshine, catching catfish, and strumming the banjo—representing stereotypical, racist views of black citizens at the time.

British artist Jonathan Yeo was commissioned by the George W. Bush Presidential Library to paint an official portrait of the 43rd president in 2007, but when the invitation was suddenly withdrawn, Yeo went ahead and made an unofficial portrait of “W” — crafted from porn. Snipping bits of naked bodies from skin magazines, Yeo constructed a dark image of the controversial but steadfast leader. While not technically a work on canvas, it would make a funny Paint by Number kit.

David Humphrey’s 2006 painting, Ike Paints From Life, reference’s Dwight D. Eisenhower love of landscape painting. The president is seen sitting at his easel with brush and paint, but the scene goes topsy-turvy from there — as trees are uprooted, rivers turn oily black, and an observing clown-faced, rabbit-eared figure drops his trousers. Strikingly surreal, Humphrey’s canvas portrays a greatly changed American landscape from the president’s time — revealing a place Ike most likely would no longer recognize.

Chuck Close’s 2007 portrait of Bill Clinton began with a photograph that Close made in 2005 for the cover of New York Magazine. Two years later, the artist asked the president if it was OK to make a painting from one of the shots and Clinton approved. Gridding the surface of the photo, Close mapped out a plan for transferring the image to canvas and filled each module with abstract marks that together form an uncanny likeness of the 42nd president. “Clinton is very seductive,” Close told a Telegraph reporter in 2007. “When he looks directly into your eyes, he has an almost laser-beam-like lock-on thing that he does. He makes you feel like he’s really connected to you.”

Folk artist Rev. Howard Finster painted Abraham Lincoln several times in his lifetime. This charming version features a young Abraham rendered in Finster’s simple, signature style with the Biblical scripture “How beautiful/upon the mountains/ that are the feet of him/ that bringeth Good Tidings” inscribed on the surface of the painting on wood and “Purpose of these/ paintings is to/ get the truth to/ people before the/ end of the world/ the end is pressing/ time now” prophetically written on the back.

We know that Shepard Fairey’s Hope portrait of Barack Obama is the most recognizable image of the president, but it’s so ingrained in our minds we don’t even have to see it to remember it. Kurt Kauper’s portrait of the president is full of hope yet strange in the way it depicts Obama waving from a serene suburb. Part of a pair of paintings that Kauper made of the president and first lady (she’s waving in a suburban parking lot) after the election, the pieces were only works on view in Kauper’s 2009 solo show at New York celebrated Deitch Projects.