When discussing important stolen and lost oil painted pictures, World War II is going to have to be addressed.The theft and purposeful destruction of numerous works of art by the Third Reich has been well-documented (the film The Rape of Europa presents a particularly good history), and just as significant were the accidental destruction of works caught in the middle of battle – collateral damage of bombings and the razing of cities. This is how one of Caravaggio’s most pivotal large original oil paintings, Saint Matthew and the Angel, met its end. When the Allies bombed Berlin in 1945, the oil portrait painting, then housed at the Kaiser-Friedrich-Museum, the painting was completely destroyed.

When it was painted in 1602, the painted portrait of the Gospel writer St. Matthew caused a scandal. Caravaggio, who often portrayed Bible elites as the poor Romans he knew and lived alongside, had gone too far in the eyes of his patron, Cardinal Matthieu Cointrel. Cointrel had hired the oil portrait painter to create three scenes from the life of his namesake, to display in a chapel in the Roman church of San Luigi dei Francesi. When Caravaggio delivered his interpretation of St. Matthew writing his Gospel, Cointrel was appalled.

It’s rare for the visual arts to make headline news, and it’s unfortunate when they do in a story like this one. On the night of May 19, a masked man entered the Musée d’Art Moderne de la Ville de Paris through a window and stole five oil painted pictures, removing them from their frames and escaping without setting off an alarm. The story quickly made headlines, partially because of the crime’s lurid intrigue and partially because of the estimated value of the words – over $120 million. Since then, we’ve all seen a picture of the painting Le pigeon aux petits pois by Picasso or of La Pastorale by Matisse alongside an article. Those two landscape portraits are usually the only ones mentioned, as the significant but lesser known Modigliani, Léger, and Braque works are often unfortunately lumped together as “three other paintings”.

What can this man possibly be planning to do with his contraband? Plenty of art thieves actually count on simply ransoming the stolen goods back to the owner. More strangely, after a painting has passed through several different owners, it can often be sold to an unknowing customer who is led to believe that the painting is a very high quality reproduction – not the work itself but a skillful oil painting from a picture of the original. What’s most likely in this situation is a third option. Although the value of a stolen painting is markedly less than the official value, the underground art market is unfortunately very healthy. The authorities seem to suspect that this is what’s happening with the five stolen oil portraits, as Interpol has issued a global alert, implying they believe the works may already have been removed from France.

Vincent & Theo

Starring: Tim Roth, Paul Rhys

Release: 1990

If you’ve been following this list, right now you might be thinking, “Wait, another Van Gogh movie?” Yes, Vincent & Theo (1990) traces the relationship and lives of brothers Vincent (played by Tim Roth) and Theo (played by Paul Rhys) Van Gogh, the oil portrait artist and his art dealer brother. The film follows the brothers’ turbulent but supportive relationship, as it also documents their individual struggles with mental deterioration. Where Lust for Life presented a dignified and sanitized version of this descent, Vincent & Theo is much more honest and brutal. Vincent’s mental illness is well known, but Theo also battled with mental deterioration caused by syphilis, and the film represents these struggles with a frankness that can be downright scary.

As it emphasizes the inner lives of the portrait painting artist and his brother, the film emphasizes the connection between those inner lives and artistic passion.

Frida

Starring: Salma Hayek, Alfred Molina

Release: 2002

Frida (2002) follows the life and work of Frida Kahlo (played here by Salma Hayek) from her youth through her death. The film represents the Mexican surrealist and self portrait painter as influenced primarily by two things: the bus accident that nearly killed her as a teenager and her two turbulent marriages to muralist Diego Rivera (played by Alfred Molina). As it focuses on such a broad expanse of experience, the film proves to embody both the very worst aspects of so-called “biopics” and the very best.

When it comes down to it, a number of the films on this list (particularly Basquiat, Pollock, and Lust for Life) all suffer from the same problem that Frida does: they try to address an entire life in the length of a few short hours, which is nearly impossible. The result is that the life is boiled down to a few events, with pictures of paintings interspersed. This can, unfortunately, give a film a bit of a hollow feel, which does happen sometimes in Frida.

Girl with a Pearl Earring

Starring: Colin Firth, Scarlett Johansson

Release: 2003

Girl with a Pearl Earring is a unique entry on this list, primarily in that the artist represented in the film, Johannes Vermeer (played by Colin Firth), really isn’t the movie’s main character. He’s a key figure to be sure and the film offers an interesting perspective on his work, but the story really revolves around a fictional character named Griet (played by Scarlett Johansson), a maid in Vermeer’s home.

After Griet shows an intelligent appreciation for her employer’s work – unsurprising, given that her father was himself a painter before being blinded and losing the use of one hand in an accident – Vermeer begins to view her as a sort of muse, basing paintings on her daily activities (particularly Woman with a Water Jug, shown below) and requesting her assistance in the mixing of paints. Eventually, the film shows her sitting as the subject of the film’s namesake, the stunning and intimate portrait Girl with a Pearl Earring. The film follows Griet’s journey as she enters into domestic servitude, spars with Vermeer’s wife and daughter, and becomes romantically involved with the local butcher’s apprentice, Pieter.