When you explore renowned government buildings or royal residences around the globe, you're bound to encounter portraits of kings, queens, and presidents from various eras. These images are often bold and commanding, serving as visual representations of authority—designed primarily as propaganda to immortalize the individuals depicted.
While many of these portraits follow traditional artistic styles, there are times when they stir up controversy, provoke curiosity, or even trigger diplomatic tensions. Below is a list of portraits of heads of state and government officials that have gained attention, for reasons both intriguing and contentious.
10. Sir Winston Churchill

Graham Sutherland’s renowned (or notorious) portrait of Winston Churchill was commissioned in 1954 by the House of Commons to celebrate the former prime minister’s 80th birthday. The piece portrays the wartime leader in a scowl, slumped in a chair against a somber backdrop.
The portrait was revealed during a ceremony at Westminster Hall, attended by Sir Winston and his wife, Lady Churchill. Churchill sarcastically referred to the portrait as “a remarkable example of modern art,” drawing laughter from the crowd. Although it was meant to be displayed publicly, the government decided to present it as a private gift to Churchill.
Lady Churchill despised the portrait. Fiercely protective of her husband's image as a celebrated war hero, she felt it misrepresented him. She disliked it so much that she, along with her secretary, Grace Hamblin, burned it. (Of course, copies of the portrait still exist.) Sutherland, understandably upset, labeled the destruction an act of vandalism. He wasn’t mistaken.
Interestingly, despite both Sir Winston and Lady Churchill’s disdain for the portrait, Lady Churchill admitted that Sutherland had accurately captured his likeness, acknowledging it was “really quite alarmingly like him.”
9. Queen Elizabeth II

Queen Elizabeth II has posed for innumerable portraits throughout the years. While many emphasize her regal role as a queen, others highlight the woman who holds the crown. When Lucian Freud was commissioned to paint her in 2001, the result stirred such controversy that it was labeled a 'travesty' by the press.
Freud's unique style, characterized by harsh colors and a seemingly brutal portrayal of the queen, was undeniably unflattering. Her expression appeared distant, and her features were depicted with a sense of weight, almost as though burdened.
While some critics dismissed the portrait as so dreadful that the artist should be imprisoned in the Tower of London, others came to Freud's defense. Charles Saumarez-Smith, the director of the National Portrait Gallery, described it as 'thought-provoking and psychologically penetrating.' Meanwhile, the chief art critic for The Times hailed it as 'painful, brave, honest, stoical, and, above all, clear sighted.'
8. Bill Clinton

Nelson Shanks, renowned for his portraits of icons like Princess Diana, Pope John Paul II, and Ronald Reagan, was commissioned to paint Bill Clinton in 2006. Known for revitalizing classical realism in portraiture, the Clinton portrait wasn’t seen as particularly controversial when it was first revealed.
Fast forward to 2015, when Nelson Shanks revealed that he had subtly referenced Monica Lewinsky in the painting, explaining, “The truth is, he’s probably one of the most infamous liars in history. His administration did some commendable things, sure, but I couldn’t shake the Monica issue, and it’s discreetly embedded in the artwork.”
So, where exactly is the reference in the portrait? If you observe closely, you’ll notice a shadow cast over the fireplace. This is thought to allude to the infamous dress worn by Monica Lewinsky during one of their encounters.
7. George H.W. Bush

Gregory Heisler, a photographer whose works have adorned the covers of Time magazine on numerous occasions, created one image in 1990 that stirred significant controversy. The double exposure photograph portrayed President George H.W. Bush with two faces. It was selected for the magazine's Man of the Year feature.
Some critics believed there was an artistic reason behind the double exposure. While Bush had some success in foreign policy, particularly regarding Iraq, his domestic achievements were less notable. Despite any artistic rationale, the image was undeniably contentious and perhaps too on-the-nose in depicting the president as literally two-faced.
The White House did not take kindly to the portrait, and as a result, Heisler’s press credentials were temporarily revoked.
6. Marie Antoinette

In the 18th century, when it came to painting kings and queens, there was a certain expectation—to capture majesty, power, and authority. So when Madame Vigee Le Brun, a celebrated female artist and close confidante of the French queen, painted Marie Antoinette in a simple muslin dress, it sparked outrage. Today, the painting seems innocent, but at the time, being portrayed in a chemise was considered scandalous, akin to being depicted in one’s undergarments.
The queen, however, was thrilled with the portrait. At the time it was painted, Marie Antoinette was stepping away from the lavish, elaborate court dresses that had unfairly contributed to her image as a reckless spender while the people suffered.
Additionally, the queen showed remarkable political insight regarding vanity during the sitting. Vigee Le Brun had suggested that Marie Antoinette forgo the typical powdered hairstyle worn by aristocrats of the time, but the queen declined, not wanting people to think she was trying to hide her prominent forehead.
5. Danish Royal Family

The Danish royal family, like their British and French counterparts, has also been subject to controversial portrayals in art. Queen Margrethe II, to mark the 150th anniversary of the Glucksburg family’s reign in Denmark, commissioned painter Thomas Kluge to create a family portrait.
However, the portrait Kluge produced stirred mixed reactions, being labeled as unsettling. The royal family is depicted in a direct stare toward the viewer, with many of the children absorbed in toys like dolls and Legos. Yet it is Prince Christian, second in line to the throne, who stands out in the center of the portrait, staring intensely at the audience, enveloped in dark shadows, evoking the sinister image of Damien from The Omen.
Kluge, taken aback by the public’s response, explained that his intention was to position the royal family within the framework of a modern democratic society, adding, 'This is satire.' Queen Margrethe, though privately unsure of the painting, graciously gave her approval.
4. Anne of Cleves

King Henry VIII had a notoriously rocky path when it came to marriage. He divorced one wife, executed another, and lost a third during childbirth. In 1539, Henry set his sights on a fourth wife, and sent his court artist, Hans Holbein the Younger, to Cleves to paint Anne and her sister. Holbein was instructed not to flatter the princesses. Upon seeing the portrait, Henry was pleased and initiated talks for Anne’s marriage.
Yet, when Anne arrived in England, Henry was taken aback, remarking, 'She is nothing so fair as she hath been reported.' Despite his disappointment, the marriage went forward, though it was never consummated.
Henry sought an annulment, and Anne wisely agreed. In gratitude, the king bestowed upon her lands, wealth, and the honorary title of the King’s Beloved Sister. Anne not only outlived Henry, but also his many other wives.
3. Queen Elizabeth II

With Queen Elizabeth II's reign spanning over six decades, it’s no surprise that numerous portraits of the monarch have been created. While some have had varying levels of success, few have garnered as much recognition as those by Andy Warhol, as noted earlier.
In 1985, the iconic artist produced the Reigning Queens series, and his prints of the British monarch quickly became the most famous. Through his distinctive screen printing method, Warhol transformed the queen into a modern pop art figure, elevating her from a respected royal to a pop culture sensation.
At the time, these portraits may have seemed controversial, but as art values and perspectives evolved, the queen herself came to recognize the worth of owning a Warhol. In 2012, she acquired the prints, solidifying their investment value.
2. Michelle Obama

Immediately after the portrait of Barack Obama was unveiled, a second artist revealed her own portrait of the former president’s wife, Michelle. It proved equally as eyebrow-raising. Amy Sherald painted the former first lady seated, dressed in a floor-length gown and sporting an elegant, calm expression.
The only problem was that the woman Sherald painted arguably doesn’t look like Michelle Obama. Art critic Holland Cotter was disappointed, saying, “I was anticipating—hoping for—a bolder, more incisive image of the strong-voiced person I imagine this former first lady to be.” Moreover, the portrait seemed to focus more on what Michelle Obama was wearing rather than the woman herself. The bold, geometric design of the gown takes up almost half the picture and draws attention away from the woman.
Despite the controversies surrounding the portraits of the former president and first lady, they nonetheless have sparked a conversation about art and artists, and that is surely a good thing.
1. Barack Obama

The latest portrait featured on our list is the official portrait of Barack Obama, which was unveiled at the National Portrait Gallery in Washington, DC, in February 2018. Painted by Kehinde Wiley, the portrait shows the first African American president of the United States sitting against a lush backdrop of vibrant green foliage. While the pose itself didn’t spark much debate, the portrait did stir controversy when rumors circulated that the artist had subtly incorporated sexual imagery, including a sperm cell painted on Obama’s head.
While this observation might have been better left to interpretation, perhaps even more unsettling than the supposed hidden sperm is the fact that Kehinde Wiley has a known history of depicting portraits of black women holding the severed heads of white women. In a 2012 interview with New York magazine, Wiley mentioned that these artworks were intended as a “play on the ‘kill whitey’ concept.”