The 20 Most Important Christmas-Themed Art Pieces of All Time

Image via Complex Original

No, it’s unlikely you’d find us purchasing a piece of art for a loved one at the local mall’s Thomas Kinkade store this holiday season. At the same time, when you consider that the late Painter of Light's work hangs in one out of every 20 homes in America, and that The Christmas Cottage is his most popular print, well, you do the mass market math.

Dubbed "The Pavement Picasso," U.K.-born pavement artist Julian Beever has dazzled unsuspecting pedestrians all over the world with his 3D chalk illusions. In 2008, he delighted shoppers (young and old) at The Atrium shopping center in Camberley, England when he applied his trompe l’oeil style to create a 3D version of Santa's workshop.

Self-taught Abstract Expressionist Richard Pousette-Dart surprised industry know-it-alls when his holiday themed Christmas Tree sold for more than 10 percent higher than its estimate ($22,325 to be exact) when it went to auction at Christie's in 2001.

Street artists sure are a philanthropic bunch. In 2010, Banksy's buddy Mr. Brainwash created less than 100 of these four-color prints, each one signed, numbered, and thumb-printed by the artist, to benefit Toys for Tots.

Pop art pioneer Richard Hamilton took a slightly darker and more commercial view of the most wonderful time of the year with this limited-edition print. Number 140/150 fetched $26,760 in 2008, when it went to auction at Christie's in London.

It takes a confident artist to ignore the advice of Paul Gauguin, which is exactly what Danish painter Viggo Johansen did when Gauguin saw Merry Christmas in its earliest stages and suggested that Johansen make the tree brighter. Johansen clearly didn't take the advice to heart.

For the past 25 years, renowned art collector and MoMA trustee Peter Norton has commissioned a series of holiday-themed works from artists included in his own collection to create a limited number of affordable pieces in a variety of mediums as a way to share one's love of art. In 2000, contemporary Japanese artist Takashi Murakami took part in the project to produce 3,000 of these plastic sculptures, perfectly sized to sit atop a desk or a mantel awaiting Santa's arrival.

Quick—can you spot the anachronism? Nativity paintings are nothing new. But Italian artist Lorenzo Lotto, whose work best fits within the Venetian school, made a very bold statement when the deeply religious artist opted to paint a crucifix behind the proud parents in his Nativity. Were Joseph and Mary aware of the their newborn's destiny?

Damien Hirst restrained his love of dots (mostly) for this foil block print, which is inscribed "For Ella" and stamped with a "Happy Christmas 2010" greeting. All 150 prints are signed and numbered.

If this image from Joseph Farquharson looks familiar, that's probably because it has been reproduced for just about every piece of holiday paraphernalia you can imagine, from greeting cards to ornaments. Amazingly, the original painting's whereabouts were unknown for many years, until its owner emerged in 2008 looking to sell—for 50 times more than the original purchase price. It sold. Quickly. And with fanfare.

Four decades after beginning work with The Coca-Cola Company, where he helped to define the modern-day version of Santa Claus, illustrator Haddon Sundblom was creating a holiday-themed piece of a slightly naughtier nature: a Christmas-themed Playboy cover. 

In 2008, Mark Ryden unveiled his largest work to date, The Creatrix, which took him an entire year to complete. Like all of Ryden's work, there's a lot going on here—but Santa Claus' outsized appearance makes classifying this as a Christmas piece appropriate. Ryden says that its meaning "is difficult to put into words… What the viewer thinks the work is about is more important than the reasons I may give. That may sound evasive, but to explain the painting takes the best part, the mystery, away from it. It’s for others to ponder and draw their own conclusions."

Andy Warhol was an artist who knew a thing or two about the holiday spirit (he created enough holiday-inspired work that Christie's was just able to put together an entire online-only auction surrounding it). And he clearly had a particular affinity for poinsettias, as evidenced by this silkscreen ink on canvas creation from 1982.

Since 1987, music producer Jimmy Iovine's A Very Special Christmas series of celeb-sung holiday classics has raised more than $100 million for The Special Olympics organization. Keith Haring's iconic work has remained the symbol of this do-gooder collaboration.

Banksy's 2004 ode to the commercialism of religious holidays paints a simple (and to some, offensive) message that is as appropriate a depiction of the Christmas season as it is the Easter holiday.

On its own, George Henry Durrie's pastoral scene of a snow-covered farm is pleasing enough, but it became an iconic image of the holiday season in 1975, when Gerald and Betty Ford chose to reproduce it on the official White House Christmas card. The original painting still hangs in The White House.

More than 150 years before 'Twas the Night Before Christmas confirmed the chimney as Santa's entryway into the homes of all good boys and girls, Dutch master Jan Steen hinted at this same scenario.

Four years before he began his legendary—and long-lasting—collaboration with the Saturday Evening Post, which included annual Christmas cover illustrations, Norman Rockwell was the art director at Boys' Life. In 1912 he created his first Santa-themed cover for that very publication. Though not his most famous Santa painting, Santa and the Scouts is a great example of an artist in the early days of his career.

Though Thomas Nast and Norman Rockwell are the two names usually associated with the creation of Santa's image as we know it today, Nast was working steadily a good five decades before Rockwell. Like Rockwell, over the years Nast would contribute near-annual depictions of Santa Claus for the cover of Harper's Weekly. His first, published on January 3, 1863, showed Santa handing out gifts to Union soldiers.

One year before his passing, Italian master Caravaggio painted this Baroque nativity scene. Exactly 360 years later, the piece was stolen from its home at the Oratory of San Lorenzo in Palermo, Sicily and has never been seen since. Valued at approximately $20 million, rumors have long abounded that the piece was stolen by the local mafia. Its whereabouts are still a hot topic, with one former mafia hitman claiming it was actually burned in the 1980s.