A misplaced elbow here. An untied shoelace there. Falling down a flight of stairs and landing on a collection of 300-year-old vases. It’s a clumsy art-lover’s worst nightmare.

From priceless native art to a $130 million Picasso, we take a look at the worst smashes, rips, shreddings and bulldozes in art history.

Lucian Freud Drawing

Lucian Freud

A drawing by Lucien Freud, valued at $157,000 and still in its wooden packing case, was accidentally placed in a crusher at Sotheby’s Auction House in 2000. Workers thought it was empty, and by the time they realized their error the crushed drawing had already been carted off to the incinerator. Lucien Freud is the grandson of Sigmund Freud, and one of the most collectible of modern British artists. The painting, an early oil study of plants dating back the 1960s, was owned by a private collector and was scheduled to be studied, photographed and catalogued for the upcoming auction.

Picasso - The Actor

The Actor

In 2010, a woman visiting the Metropolitan Museum in New York “lost her balance” and crashed through a $130 million Picasso painting. Her fall caused a 6-inch gash in the ‘The Actor,’ one of Picasso’s larger paintings. Museum experts were able to fix the tear, but the painting has since lost half of its value. The woman was uninjured.

Qing Dynasty Vases

Qing Dynasty Vases

While Nick Flynn was visiting Cambridge’s Fitzwilliam Museum in 2006, he had an unfortunate incident involving a loose shoelace, a lack of handrails and a $550,000 collection of Qing Dynasty vases. According to Flynn, disaster struck after he went up the wrong staircase and swung around to come down. He tripped on his untied shoelace, fell down the stairs and hit the first vase, which knocked over two more. Museum workers spent several months gluing the 400 pieces back together. And by gluing, I mean carefully restoring the vases using ceramic conservation techniques. They’re now back on display in a specially-designed case.

Picasso - La Reve

La Reve

Billionaire Steve Wynn, a casino magnate, real estate mogul and art collector, inadvertently put his elbow through one of the paintings in his office, leaving a small hole. Unfortunately, the painting was a $139 million Picasso painting that he had just agreed to sell. The painting, called ‘La Rêve’ (‘The Dream’), depicts Picasso’s 22-year-old mistress, Marie-Thérèse Walte.
Before the accident, the painting would have been the most expensive piece of art ever sold. After a $90,000 repair, the painting was re-valued at $85 million.

Giorgio de Chirico - Piazza d'Italia

Piazza d’Italia

‘Piazza d’Italia,’ a painting by Italian artist Giorgio de Chirico, was worth hundreds of thousands of dollars before a wrecking ball smashed a huge hole in the middle of it. The painting was part of a private collection that had the misfortune of being hung next door to a bank that was being demolished. The crane operator accidentally swung through the collector’s living room wall and permanently destroyed the de Chirico. Thankfully, the painting was insured.

Wampanoag Village

Wampanoag Village

In 1987, a bulldozer operator accidentally destroyed an 800-year-old Native American village near Plymouth, Mass, when he graded the wrong the property. Known as Nook Farm in recent years, the 5.5 acre site would have given archaeologists a rare glimpse into Pre-European American culture. Prior to the accident, archaeologists had unearthed 12,000 artifacts dating back to 6000 years, including clay pots, soapstone art and various human and animal bones. Archaeologists have been aware of the site for over a century, and had left it unmarked because of the possibility of looting.