No other painting by El Greco takes on a classical myth quite like Laocoön, and it is the only known work where the artist sets an ancient Greek legend in the rolling hills of his adopted city, Toledo. This bold relocation has puzzled viewers and scholars alike, as El Greco was famed for his religious scenes, not for tales from Homer. The painting’s date remains uncertain, but it was likely created late in the artist’s life, when his style had reached its most expressive and experimental form.

The myth itself had been a favorite of Renaissance artists, yet El Greco’s version stands alone for its stormy, haunted mood and its departure from classical ideals. At the center of the canvas, the doomed Trojan priest Laocoön writhes in agony as monstrous serpents—sent by the gods—coil around him and his sons. According to the myth, Laocoön had warned his people against bringing the Greeks’ wooden horse into Troy, earning the wrath of Athena or Poseidon. El Greco captures the moment of divine punishment: the figures' elongated limbs twist in unnatural poses, their faces contorted in terror and pain.

The sky churns with dark, swirling clouds, echoing the chaos below, while the city of Toledo looms in the background, its towers and walls standing in for ancient Troy. Unlike the harmonious marble group of the same subject in the Vatican, El Greco’s vision is restless and jagged, emphasizing human agony over heroic beauty. The origins and early history of Laocoön are shrouded in uncertainty; there is no record of a specific patron or commission. The work remained in Spain after El Greco’s death and was not widely known outside Toledo for centuries.

Its bold style and mythological subject have made it a subject of debate among art historians, who see it as both a personal statement and a challenge to classical tradition. Today, Laocoön is recognized as a singular achievement within El Greco’s oeuvre, marking his only foray into pagan myth and reflecting the unique blend of Venetian color, Byzantine form, and Spanish mysticism that defines his late period. The painting now hangs in the National Gallery of Art in Washington, D.C., where it continues to intrigue and unsettle viewers.