Anticipating the Inaugural, we used Grok (X’s A.I. tool) to ask 47 deceased artists to do portraits of all 47 presidents. Some images are exactly what Grok generated. Others needed edits for color, texture, etc. For maybe half the images, we specified the artist beforehand (e.g., “Portrait of Jefferson in the style of Warhol”). For others, we specified a style (e.g., “FDR as a WPA mural”) and then searched for artists whose works looked similar to the result. Some queries were simple; others, intricate. Below, you’ll find the connections between each president and his “portraitist.” PLEASE SHARE WITH FANS OF HISTORY, POLITICS, ART, AND/OR A.I.
ANTIQUITY (1789-1829)
Paul Johnson’s THE BIRTH OF THE MODERN says everything changed between 1815 and 1830, including arts, clothes, etiquette, and politics. Science, medicine, engineering, and transport changed more than in the previous 2,000 years. The first four presidents preceded this period. The latter two oversaw it.
[1] GEORGE WASHINGTON/by unnamed 14th Century Byzantine iconographer. GW’s image is saintly and ancient. He alone died in the 18th Century, perhaps from medical treatments unchanged since Ancient Rome and debunked before his successors died.
[2] JOHN ADAMS/Fra Angelico (1395-1455). I asked Grok to place the frugal JA in a spare Salem meeting house. The light and tone looked like Fra Angelico.
[3] THOMAS JEFFERSON/Andy Warhol (1928-1987). TJ swam with the trendy in Paris and curated American fashion. 150 years later, he would have partied with Warhol.
[4] JAMES MADISON/Jared French (1905-1988). JM’s genius created a legal system capable of holding together a vast republic. So I asked Grok to pose him before a temple of law in a sweeping vista. The output looked WPA-style. A search of WPA artists yielded works by French in similar style (e.g., SUMMER’S ENDING).
[5] JAMES MONROE/Diego Rivera (1886-1957). The Monroe Doctrine fused the U.S. to Latin America, so I asked for Monroe by Rivera. For me, Monroe casts wary eyes toward Europe.
[6] JOHN QUINCY ADAMS/Johannes Vermeer (1632-1675). JQA was a chilly New Englander but fiery Abolitionist. I see his bare chamber darkened by slavery, with light entering over his law books. The lighting looked Vermeer-ish.
EMPIRE (1829-1850)
The Missouri Compromise contained slavery long enough for the Texas Annexation, Oregon Treaty, and Mexican Cession to build a transcontinental empire. Only 1854’s Gadsden Purchase remained to fill out the Lower 48 states.
[7] ANDREW JACKSON/Francisco Goya (1746-1828). AJ could be as terrifying as Goya’s nightmarish visions.
[8] MARTIN VAN BUREN/Childe Hassam (1859-1935). MvB’s foppish style obscures his modest upbringing in a Dutch-speaking family. (The only president who spoke English as a second language.) The brush strokes and flag recall Hassam.
[9] WILLIAM HENRY HARRISON/Andrew Wyeth (1917-2009). WHH’s slogan, “Born in a Log Cabin,” was primordial campaign-consultant BS. (He was born to wealth and power on a Virginia plantation.) The image struck me as Wyeth-esque.
[10] JOHN TYLER/John Singer Sargent (1856-1925). JT was reviled, but impactful, so I asked for black and red. The result recalled Sargent’s DR. POZZI AT HOME. Trivia: Tyler (1790-1862) still has one grandson alive today.
[11] JAMES K. POLK/Maynard Dixon (1875-1946). JKP conquered the American West, which he never visited, so we gave him a posthumous vacation. I asked Grok for a portrait in Santa Fe Style, and the output resembled Dixon.
[12] ZACHARY TAYLOR/carving by unnamed Mexican War veteran. Grok has zero idea what ZT looked like. He was a legendary general, beloved by his troops (aka “Old Rough and Ready”), so I figured one might have made such a carving.
MAELSTROM (1850-1877)
Under Fillmore, Pierce, and Buchanan, America spiraled into Civil War. Lincoln coincided with that war. Johnson and Grant oversaw its aftermath.
[13] MILLARD FILLMORE/Utagawa Kuniyoshi (1791-1868). MF was instrumental in opening Japan to world trade.
[14] FRANKLIN PIERCE/Albert Pinkham Ryder (1847-1917). Grok couldn’t draw FP, so I focused on FP’s emotional absence from the presidency. He saw his teenage son killed in a train wreck on the way to the Inauguration and spent his term in depression and alcohol. He walked away from the boiling battle over slavery. My wife said the image looked like a Ryder.
[15] JAMES BUCHANAN/Phil Connors (Pittsburgh TV weatherman and ice sculptor). JB arrived at the presidency with a stunning résumé, but as war approached, he froze and melted like ice. Connors is the only one of the 47 artists who isn’t dead; but, he’s not alive, either, and he chose to carve the only Pennsylvania president.
[16] ABRAHAM LINCOLN/John Tenniel (1820-1914). Lewis Carroll and John Tenniel collaborated on ALICE IN WONDERLAND—written during Lincoln’s term and published months after. “Down, down, down. Would the fall never come to an end?” Carroll asked of Alice, and Americans asked the same of their warring country.
[17] ANDREW JOHNSON/unnamed tobacco company artist. AJ is a North Carolinian—so, tobacco. His bigotry and policies fomented the KKK’s rise, so I wanted shadowy men behind him on the label. Curiously, Grok added shadowy men behind the can, too.
[18] ULYSSES S. GRANT/Peter Hurd (1904-1984). USG was a serious president whose administration was marred by underlings’ scandals. I asked for a period etching, but the style reminded us more of certain Hurd works.
RESPITE (1877-1897)
These six presided over relative calm, when embers of the Civil War had largely died down and the kindling of World War I had not yet ignited. Quietly nonchalant, these were the Gen X of presidents.
[19] RUTHERFORD B. HAYES/unnamed Paraguayan woodcarver. RBH is little-remembered here but a national hero in Paraguay. He successfully arbitrated the end of the bloody Paraguayan War.
[20] JAMES A. GARFIELD/Auguste Rodin (1840-1917). JAG’s assassination killed one of our most erudite, charismatic presidents. (Read Candice Millard’s DESTINY OF THE REPUBLIC.) A master of classical languages, he grew bored in Congress one day and devised a new proof of the Pythagorean Theorem. I requested a Rodin in Ancient Greek garb, and Grok added the temple.
[21] CHESTER A. ARTHUR/Charles E. Barber (1840-1917). CAA’s accession profoundly changed him and the government forever—hence, Janus. A lightweight hack from a corrupt machine, CAA was transformed by JAG’s killing. He renounced his oily patrons and transformed the government from Spoils System to Civil Service. (Millard movingly describes his redemption.) [NOTE: This is the only portrait not generated by Grok and whose pretend-creator actually had a hand in the design. Grok can’t draw CAA, so I took an actual CAA medallion, designed by Barber, split CAA in half, made a copy, flipped it around, welded the two together, and built a planchet around them.]
[22] GROVER CLEVELAND/unnamed engraver at the Bureau of Engraving and Printing. GC was deeply concerned with banking and finance, so I asked for an image one might find on a piece of currency. (He forgot to wear his bowtie.)
[23] BENJAMIN HARRISON/Henri Cartier-Bresson (1908-2004). BH was an earnest, forgettable figure who said his re-election defeat felt as if he had been freed from prison. I asked for a Cartier-Bresson “decisive moment” photo of him fleeing jail.
[24] GROVER CLEVELAND/Augustus Saint-Gaudens (1848-1907). GC was a gold-standard dinosaur in a party smitten by Williams Jennings Bryan and silver. Saint-Gaudens designed the gorgeous gold double eagle minted 1907-1933.
EMERGENCE (1897-1929)
After the calm, storm clouds returned, with America emerging as a world power. McKinley prosecuted the Spanish-American War, Roosevelt fought in it, and Taft was later his Secretary of War. Wilson, re-elected on “HE KEPT US OUT OF WAR,” promptly led America into World War I. Harding was elected to calm postwar nerves, and Coolidge closed the doors to immigration.
[25] WILLIAM McKINLEY/Georges Seurat (1859-1891). WM was the last 19th century president, whose old-fashioned ways fit Seurat’s A SUNDAY ON LA GRANDE JATTE. So, I asked for Seurat’s style, with a flag evoking the Spanish-American War.
[26] THEODORE ROOSEVELT/unnamed poster artist for Buffalo Bill’s Wild West Show/Congress of Rough Riders of the World. TR exuberantly reinvented the presidency and launched America onto the world stage. The Rough Riders he led in battle were named for Buffalo Bill’s “Congress.” Mark Hanna called TR “that damned cowboy.” Daughter Alice said, “My father always wanted to be the corpse at every funeral, the bride at every wedding and the baby at every christening.”
[27] WILLIAM HOWARD TAFT/Fernando Botero (1932-2023). WHT was an able president and abler Chief Justice. But he’s best remembered as the heaviest U.S. president, so I asked Botero to paint him.
[28] WOODROW WILSON/Edvard Munch (1863-1944). WW was perhaps the scariest president ever—a preening, moralizing racist who laid waste to the 20th Century, I asked for a portrait like Munch’s THE SCREAM.
[29] WARREN G. HARDING/Daniel Chester French (1850-1931). WH’s decent presidency was marred by corrupt underlings and a pregnant young mistress. He presided over the Lincoln Memorial dedication, featuring French’s statue. Lincoln’s son Robert was there, though he was wary of being around presidents after having been in the vicinity of all three prior presidential assassinations.
[30] CALVIN COOLIDGE, Grant Wood (1891-1942). CC was a stern-faced, laconic small-towner, so I asked for a portrait mimicking Woods’s AMERICAN GOTHIC.
EARTHQUAKES (1929-1969)
These six presided over the Great Depression, World War II, the beginning of the Cold War, the Civil Rights Movement, and Vietnam.
[31] HERBERT HOOVER/Will Eisner (1917-2005). HH was brilliant and accomplished, but the Depression destroyed his presidency. I asked Grok for an image in the style of a dark, graphic novel, and the result reminded my wife of Eisner.
[32] FRANKLIN D. ROOSEVELT/Seymour Fogel (1911-1984). FDR created the New Deal, so I asked for a WPA mural with an industrial background. The result resembled some of Fogel’s Post Office murals.
[33] HARRY S TRUMAN/Salvador Dalí (1904-1989). HST launched the Cold War as clocks ticked toward possible nuclear war. So I asked for Dalí’s melting clocks.
[34] DWIGHT D. EISENHOWER/Pablo Picasso (1881-1973). DDE led history’s greatest military struggle, whose horrors recall Picasso’s GUERNICA. The face is a sort of blend of DDE and Picasso himself. I could have sought a better image, but my wife said portraitists often subconsciously incorporate their own features into subject’s faces.
[35] JOHN F. KENNEDY/Keith Haring (1958-1990). Like TR and Clinton, JFK was a pop-culture figure, so I asked for a Haring.
[36] LYNDON B. JOHNSON/unnamed Texas muralist. LBJ was forever tormented by his down-home image and by adulation for JFK. So I asked Grok to have a less-than-stellar artist paint him on the brick wall of a West Texas barbershop.
ADJUSTMENT (1969-2001)
With World War II behind, America struggled with culture and policy. Nixon, Ford, and Carter fomented inflation, unemployment, gas lines, and loss of national confidence. Reagan restored the national spirit. Bush safely concluded the Cold War. Clinton successfully triangulated afterward.
[37] RICHARD NIXON/El Greco (1541-1614). RMN’s brilliance was tarnished by paranoia and scandal. I wanted something both imposing and disturbing, so I asked Grok to combine RMN and El Greco’s VIEW OF TOLEDO.
[38] GERALD R. FORD/Raymond Loewy (1893-1986). GRF’s years featured horrid fashions and gas lines, so I asked for a portrait with both. I added the WIN button later. From the colors, it appears to be a Shell station. Loewy designed Shell’s aesthetic and Air Force One’s—and he and GRF lived near one another in the Palm Springs area. So, retroactively, this became a Loewy.
[39] JIMMY CARTER/Rembrandt van Rijn (1606-1669). JC was a humorless, judgmental scold—like some early Calvinist. Hence, Rembrandt’s chiaroscuro.
[40] RONALD REAGAN/unnamed mid-19th Century Harper’s Weekly engraver. RR’s optimism was a sharp departure from JC’s malaise. An old-fashioned character, he seemed right for a 19th century Harper’s pic.
[41] GEORGE H. W. BUSH/Chuck Close (1940-2021). GHWB was serious, intense, and a bit bland—like most Chuck Close subjects.
[42] BILL CLINTON/Roy Liechtenstein (1923-1997). Like TR and JFK, BC had an outsized pop-icon personality, so I asked for a Liechtenstein. Coincidentally, the real Liechtenstein created a campaign button for BC.
POLARIZATION (2001-date)
The 21st century has seen bitter political polarization, fueled by, among other things, social media. Bush, Obama, Biden, and Trump would comprise a rather rancorous bridge party.
[43] GEORGE W. BUSH/Thomas Hart Benton (1889-1975). GWB’s personality and the Texas Hill Country are sunny, so, I asked Grok for GWB by Benton.
[44] BARACK OBAMA/Edward Hopper (1882-1967). BHO’s personality is cool, intense, and broodingly pensive. Hopper seemed a natural.
[45] DONALD TRUMP/Gustav Klimt (1862-1918). DJT’s glitzy aesthetic has been a cultural staple for decades—reflected here by Klimt’s golden swirls and glittery jewels.
[46] JOE BIDEN/Vivian Maier (1926-2009). JB is a diminished figure, in mental and physical decline for most of his term. Discarded and deserted by his own party, he recalls Maier’s lonely street characters.
[47] DONALD TRUMP/Hans Hoffman (1880-1966). DJT returns in a different mood from the first time around. Hoffman uses a bold-colored “push and pull” technique to create tension—a phrase that well-describes the re-emergent Trump.
A pleasant potted history of the presidency to accompany the portraits. The hair on the Zachary Taylor figure is odd, like he is wearing a whig. There are some good artists to explore further. Are there plans for this to be a poster one could purchase? (captions included, of course). Thanks!
Bravo, Bob & Alanna! Fantastic article. Exhibit 1 on great creative use of AI. The Buchanan/Phil Connors is one of several laugh-out-loud touches. This is a keeper!