One funny haircut story involves a mother who asked the stylist to trim her young son's curls. After going next door for a beverage, she came back, and much to her dismay and horror, saw that all the curls had been completely removed. The hairdresser exclaimed that the boy looked like a college student. The mother had to admit that he certainly had a new identity.
Another haircut story involves a blog account, which conveys a woman's nervousness about having to sit in silence while a beauty school student cuts her hair. In her account, she says that any quietude makes her anxious, and when she feels that way, she cannot seem to shut up. She notes that is why she would not make a credible witness at a trail. She would start out as the witness and talk herself into being the prime suspect.
In yet another story, one model did not find her haircut so funny. She agreed to getting her strands sheared by a Miami stylist who said she'd cut her hair for free. However, the model said she had to wear wigs after the cut for photo shoots and similar modeling gigs. She blamed the new "style" for hurting her career.
Apparently, many funny or sad haircut stories involve a stylist who is a bit too exuberant about cutting hair.