Artists throughout history have never shied away from controversy—in fact, many even try to court infamy. (Need proof? Just look at Banksy, the anonymous street artist who recently created a work that self-destructed the moment it was sold at auction—for a whopping $1.37 million.) While it’s up to critics and historians to debate technique and artistic merit, there are some works of art that shocked most people who saw them. From paintings deemed too lewd, too rude or too gory for their time to acts of so-called desecration and powerful political statements, these are some of the most controversial artworks ever created.

1. Michelangelo, “The Last Judgement,” 1536–1541

Some 25 years after completing the Sistine Chapel ceiling, Renaissance polymath Michelangelo returned to the Vatican to work on a fresco that would be debated for centuries. His depiction of the Second Coming of Christ in “The Last Judgement,” on which he worked from 1536 to 1541, was met with immediate controversy from the Counter-Reformation Catholic church. Religious officials spoke out against the fresco, for a number of reasons, including the style with which Michelangelo painted Jesus (beardless and in the Classic style of pagan mythology). But most shocking of all were the painting’s 300 figures, mostly male and mostly nude. In a move called a fig-leaf campaign, bits of fabric and flora were later painted over the offending anatomy, some of which were later removed as part of a 20th century restoration.

2. Caravaggio, “St. Matthew and the Angel,” 1602

Baroque painter Caravaggio’s life may be more controversial than any of his work, given the fact that he died in exile after being accused of murder. But his unconventionally humanistic approach to his religious commissions certainly raised eyebrows in his day. In the now-lost painting “St. Matthew and the Angel,” created for the Contarelli Chapel in Rome, Caravaggio flipped convention by using a poor peasant as a model for the saint. But what upset critics the most were St. Matthew’s dirty feet, which illusionistically seemed to jut from a canvas (a recurring visual trick for the artist), and the way the image implied him to be illiterate, as though being read to by an angel. The work was ultimately rejected and replaced with “The Inspiration of St. Matthew,” a similar, yet more standard, depiction of the scene.

3. Thomas Eakins, "The Gross Clinic," 1875

This icon of American art was created in anticipation of the nation’s centenary, when painter Thomas Eakins was eager to show off both his talent and the scientific advances of Philadelphia’s Jefferson Medical College. The realist painting puts the viewer in the center of a surgical amphitheater, where physician Dr. Samuel Gross lectures students operating on a patient. But its matter-of-fact depiction of surgery was deemed too graphic, and the painting was rejected by the Philadelphia Centenary Exhibition (some blame the doctor’s bloody hands, others argue it was the female figure shielding her eyes that put it over the edge). However, a century later, the painting has finally been recognized as one of the great masterpieces of its time on both its artistic and scientific merits.

4. Marcel Duchamp "Fountain," 1917

When iconoclastic Marcel Duchamp anonymously submitted a porcelain urinal signed “R. Mutt 1917” as a “readymade” sculpture to the Society of Independent Artists, a group known to accept any artist who could come up with the fee‚ the unthinkable happened: the piece was denied, even though Duchamp himself was a cofounder and board member of the group. Some even wondered if the piece was a hoax, but Dada journal The Blind Man defended the urinal as art because the artist chose it. The piece marked a shift from what Duchamp called “retinal,” or purely visual, art to a more conceptual mode of expression—sparking a dialogue that continues to this day about what actually constitutes a work of art. Though all that remains of the original is a photograph by Alfred Stieglitz (who threw the piece away) taken for the magazine, multiple authorized reproductions from the 1960s are in major collections around the world.

5. Robert Rauschenberg, “Erased De Kooning," 1953

In some ways, Robert Rauschenberg’s “Erased De Kooning” presaged Banksy’s self-destructing painting. But in the case of the 1953 drawing, the artist decided the original artwork must be important on its own. “When I just erased my own drawings, it wasn’t art yet,” Rauschenberg told SFMoMA in 1999. So he called upon the most revered modern artist of the day, the mercurial abstract expressionist Willem de Kooning, who, after some convincing, gave the younger artist a drawing with a mix of grease pencil art and charcoal that took Rauschenberg two months to erase. It took about a decade for word of the piece to spread, when it was met with a mix of wonder (Was this a young genius usurping the master?) and disgust (Is it vandalism?). One person not particularly impressed was de Kooning himself, who later told a reporter he initially found the idea “corny,” and who some say resented that such an intimate interaction between artists had been shared with the public.

6. Yoko Ono, “Cut Piece,” 1964 / Marina Abramovic, “Rhythm 0,” 1974

As performance art emerged as an artistic practice in the postwar years, the art form often pushed toward provocation and even danger. In Yoko Ono’s “Cut Piece,” a 1964 performance, the artist invited the audience to take a pair of scissors and cut off a piece of her clothing as she sat motionless and silent. “People were so shocked they did not talk about it,” she later recalled.

Ten years later, Marina Abramovic unknowingly revisited the concept with “Rhythm 0,” in which the artist provided the audience with 72 objects to do what they “desired." Along with scissors, Abramovic offered a range of tools: a rose, a feather, a whip, a scalpel, a gun, a bullet, a slice of chocolate cake. Over the course of the six-hour performance, the audience became more and more violent, with one drawing blood from her neck (“I still have the scars,” she has said) and another holding the gun to her head, igniting a fight even within the gallery (“I was ready to die”). The audience broke out in a fight over how far to take things, and the moment the performance ended, Abramovic recalled, everyone ran away to avoid confronting what had happened. Since then, Abramovic has been called the godmother of performance art, with her often-physically-extreme work continuing to polarize viewers and critics alike.

7. Judy Chicago, “The Dinner Party,” 1974–79

With her “Dinner Party,” Judy Chicago set out to advocate for the recognition of women throughout history—and ended up making art history herself. A complex installation with hundreds of components, the piece is an imagined banquet featuring 39 women from throughout mythology and history—Sojourner Truth, Sacajawea, and Margaret Sanger among them—each represented at the table with a place setting, almost all of which depict stylized vulvas. With its mix of anatomical imagery and craft techniques, the work was dubbed vulgar and kitschy by critics, and it was quickly satirized by a counter-exhibition honoring women of “dubious distinction.” But despite the detractors, the piece is now seen as a landmark in feminist art, on permanent display at the Brooklyn Museum.

8. Maya Lin, “Vietnam Veterans Memorial,” completed 1982

Maya Lin was only 21 when she won the commission that would launch her career—and a national debate. Her design for the Vietnam Veterans Memorial was chosen by a blind jury, who had no idea the winning designer was an architecture student. While the proposed design fit all the requirements, including the incorporation of 58,000 names of soldiers who never returned from the war, its minimalist, understated form—two black granite slabs that rise out of the earth in a “V,” like a “wound that is closed and healing,” Lin has said—was immediately subject to political debate by those who felt it didn’t properly heroize the soldiers it honors. One veteran called the design a “black gash of shame,” and 27 Republican congressmen wrote to President Ronald Reagan demanding the design not be built. But Lin advocated for her vision, testifying before Congress about the intention behind the work. Ultimately it came down to a compromise, when a runner-up entry in the competition featuring three soldiers was added nearby to complete the tribute (a flag and Women’s Memorial were also added later). As the distance from the war has grown, criticism of the memorial has faded.

9. Ai Weiwei, “Dropping a Han Dynasty Urn,” 1995

Chinese artist and activist Ai Weiwei is one of art’s most provocative figures, and his practice often calls into question ideas of value and consumption. In 1995 the artist nodded to Duchamp with “Dropping a Han Dynasty Urn,” a piece he called a “cultural readymade.” As the title implies, the work consisted of dropping, and thus destroying, a 2,000-year-old ceremonial urn. Not only did the vessel have considerable monetary value (Ai reportedly paid several hundred thousand dollars for it), but it was also a potent symbol of Chinese history. The willful desecration of an historic artifact was decried as unethical by some, to which the artist replied by quoting Mao Zedong, “the only way of building a new world is by destroying the old one.” It’s an idea Ai returns to, painting a similar vessel with the Coca Cola logo or bright candy colors as people debate whether he’s using genuine antiquities or fakes. Either way, his provocative body of work has inspired other acts of destruction—like when a visitor to a Miami exhibition of Ai’s work smashed a painted vessel in an illegal act of protest that mirrored the Ai’s own.

10. Chris Ofili, “The Holy Virgin Mary,” 1996

It’s hardly shocking that an exhibition called “Sensation” caused a stir, but that’s just what happened when it opened in London in 1997 with a number of controversial works by the so-called Young British Artists: Marcus Harvey’s painting of killer Myra Hindley, Damien Hirst’s shark-in-formaldehyde sculpture, a installation by Tracey Emin titled “Everyone I Have Ever Slept With (1963–1995),” and Marc Quinn’s self portrait sculpture made of blood. When the show hit the Brooklyn Museum two years later, it was “The Holy Virgin Mary,” a Madonna by Chris Ofili that earned the most scorn. The glittering collage contained pornographic magazine clippings and hunks of resin-coated elephant dung, which media outlets erroneously reported was “splattered” across the piece. New York mayor Rudy Giuliani threatened to pull the city’s $7 million grant for the show, calling the exhibition “sick stuff,” while religious leaders and celebrities joined the protests on opposite sides. Two decades later, Ofili’s controversial painting has earned a place in the arc of art history—and in the permanent collection of the Museum of Modern Art.