Dishes that were intended to be eaten as well as entertain can be traced back at least to the early Roman Empire. In his Satyricon the Roman writer Petronius describes a dish consisting of a rabbit dressed up to look like the mythical horse Pegasus. The earliest mention of a specified entremet can be found in an edition of Le Viandier, a medieval recipe collection, from ca 1300. It described a comparatively simple dish; boiled and fried chicken liver with chopped giblet with ground ginger, cinnamon, cloves, wine, verjuice, beef buillon and egg yolks served with cinnamon on top, and was supposed to be of a bright yellow color. An even simpler dish, like millet boiled in milk and seasoned with saffron, was also considered to be an entremet. The most noticeable trait of the early entremets was the focus on vivid colors. Later on the entremets would take the shape of various types of illusion foods, such as peacocks or swans that were skinned, cooked, seasoned and then redressed in their original plumage (or filled with the meat of tastier fowl) or even scenes depicting contemporary human activities, such as a knight in the form of a grilled capon equipped with a paper helmet and lance, sitting on the back of a roast piglet. Elaborate models of castles made from edible material was a popular theme. At a feast dedicated to Pope Clement VI, one of the Avignon popes, in 1343, one of the entremets was a castle with walls made from roast birds, populated with cooked and redressed deer, wild boar, goat, hare and rabbit.
Starting around 1300 the entremets began to involve not just eye-catching displays of amusing haute cuisine, but also more prominent and often highly symbolic forms of inedible entertainment. In 1306, the knighting of the son of Edward I included performances of chanson de geste in what has has been assumed to be part of the entremets. During the course of the 14th century they would often take on the character of theatrical displays, complete with props, actors, singers, mummers and dancers. At a banquet held by Charles V in honor of Emperor Charles IV in 1378, a huge wooden model of the city of Jerusalem was rolled in before the high table. Actors portraying the crusader Godfrey of Bouillon and his knights then sailed into the hall on a miniature ship and reenacted the capture of Jerusalem in 1099. In late medieval and early modern England, entremets are referred to as subtleties from the late 14th century and onwards. The English term was derived from an older meaning of the word "subtle" with the meaning "clever" or "surprising". The English term did not include entertainment involving actors and these were reffered to as pageants.
At the end of the Middle Ages, the level of refinement among the noble and royal courts of Europe had increased considerably, and the demands of powerful hosts and their rich dinner guests resulted in ever more complicated and elaborate creations. Chiquart, cook to Amadeus VIII, Duke of Savoy, described an entremet entitled Castle of Love in his 15th century culinary treatise Du fait de cuisine ("On cookery"). It consisted of a giant castle model with four towers, carried in by four men. The castle contained, among other things, a roast piglet, a swan cooked and redressed in its own plumage, a roast boar's head and a pike cooked and sauced in three different ways without having been cut into pieces, all of them breathing fire. The battlements of the castle were adorned with the banners of the Duke and his guests, manned by miniature archers, and inside the castle there was a fountain that gushed rosewater and spiced wine.
Entremets also made an effective tool for political displays. One of the most famous examples is the the so-called Feast of the Pheasant, arranged by Philip the Good of Burgundy in 1454. The theme of the banquet was the fall of Constantinople to the Ottoman Turks in 1453, and included a vow by Philip and his guests to retake the city in a crusade, though this was never actually realized. There were several spectacular displays at the banquet referred to by contemporary witnesses as entremets. Guest were entertained by a wide extravagant displays in the form of automatons in the form of fountains and pies containing musicians. At the end of the banquet, an actor representing the Holy Church rode in on an elephant and read a poem about the plight of Eastern Christianity under Ottoman rule.