Philippe le Picard's Laborer (c. 16th Century)
Because of several accounts detailing the uncertainty of attaching a pair of wings to one's arms and falling several stories, there were many stories and moral tales describing the dangers of flight attempts before the beginning of modern aviation. One 16th-century writer named Phillippe le Picard, who went by the penname of Philippe d-Alcripe, wrote one such story, infusing his fable with a bit of humor.
Le Picard's moral tale involves a French laborer, known across Normandy as a great swearer and drunkard. The fable says that one day, when the laborer had too much curdled milk to drink, he decided on a whim to make himself a flying apparatus and have a bit of fun. Without notifying his wife (who most likely would've scolded and slapped him into his senses), the worker cut a winnowing basket, used to separate corn kernels from husks, in half, fashioning them to his back. After failing to lift himself off the ground, the man got a brilliant idea: He needed to find a tail in order to look and act more like a bird.
Being a laborer, the man had a nearby shovel, which he placed between his legs and secured with his belt. Climbing to the top of a nearby pear tree, he jumped off, soared through the air for a split second and then fell headfirst to the ground, where he broke his shoulder. The shoulder never healed properly, preventing him from making any more drunken, misguided attempts.
Although le Picard's story is fictional, these kinds of experiments were common in that era. The following story, however, is probably the first attempt at human flight to be recorded in history.