Ichabod Crane treated his students with a mix of sternness and fairness, typical of the education standards of his time. He believed in "spare the rod, spoil the child," administering punishment primarily to stronger students while sparing the weaker ones. Despite his strictness, Ichabod aimed to fulfill parental roles, engaging with students in extracurricular activities and maintaining a professional distance. His approach combined discipline with a degree of kindness and consideration for individual student needs.

Ichabod Crane is an anti-hero in "The Legend of Sleepy Hollow." His cowardice, avarice, and peculiar appearance are all in opposition to the archetypal hero. Brom Bones is a much more conventionally heroic figure.

Ichabod Crane's large appetite for food and ghost stories makes him an easy target for Brom Bones' tricks. Crane's gullibility and superstition, alongside his vivid imagination, lead him to believe in the supernatural tales he hears, making him susceptible to Brom's mischief. Brom, who is eager to eliminate Ichabod as a rival for Katrina Van Tassel's affections, exploits Crane's fears, likely impersonating the Headless Horseman to scare him away.

Ichabod Crane can be described as a teacher and singing master by profession. Physically, he is tall, skinny, thin, awkward, and emaciated, with a nerdy appearance. His personality traits include being effeminate, weak, cowardly, envious, greedy, gluttonous, and prideful. Ichabod is a "yes" man, easily frightened despite his interest in spooky tales, and lacks high moral standards. He is slothful, working mainly out of necessity rather than ambition.

Ichabod Crane's main job is as the schoolmaster in Sleepy Hollow, where he teaches in a one-room schoolhouse. For extra income, he works as a singing teacher, providing choir lessons to the community. Additionally, he assists farmers with light chores like haying and mending fences, and occasionally babysits. These roles allow him to integrate into the community, save on expenses, and pursue romantic interests, such as Katrina Van Tassel, for potential financial gain.

Ichabod Crane demonstrates his gullibility by eagerly believing in the supernatural tales told by the townspeople, particularly the old Dutch wives. He is fascinated by the story of the Headless Horseman, a ghostly Hessian soldier, and becomes frightened by every shadow and sound when walking through Sleepy Hollow at night. His belief is so strong that he is ultimately chased away by what he perceives to be the Headless Horseman, possibly Brom Bones in disguise.

Ichabod Crane's competence as a teacher is questionable due to his biased discipline methods and self-serving behavior, such as favoring students with pretty sisters or good-cooking mothers. These actions suggest he was unfair and possibly devious. Regarding his disappearance, it is likely that Ichabod fled the town out of embarrassment and fear after being disappointed by Katrina and being spooked by his own vivid imagination of the supernatural.

Women consider Ichabod Crane important because he is an educated man in a rural community, which elevates his social status just below the parson. As a schoolmaster and singing instructor, he is seen as a gentleman with superior tastes and accomplishments. His education and storytelling, especially about the supernatural, intrigue the women, who view him as a leader and authority figure. His presence in their homes is a source of excitement and honor.

Ichabod Crane's fate after leaving the Van Tassels' party is left ambiguous. He mysteriously disappears after being chased by the Headless Horseman, with some speculating he was spirited away or met with foul play. Others believe he fled the town out of shame and fear, eventually moving to another area to restart his life.

Brom Bones recounts a tale of encountering the Headless Horseman while returning from Sing Sing. During the encounter, Brom challenged the ghostly rider to a race, with a bowl of punch as the prize. Brom took the lead, but as they neared the church bridge, the ghostly rider and his horse suddenly vanished in a flash of fire. This story later haunts Ichabod Crane as he rides home on his horse, Gunpowder.

Two actions Brom Bones takes against Ichabod for courting Katrina include harassing him by plugging up the chimney of his singing school and breaking into the school to rearrange his things, making Ichabod think he has supernatural enemies. Additionally, Brom disguises himself as the Headless Horseman and frightens Ichabod, ultimately scaring him away from Sleepy Hollow.

Brom Bones plans to counter Ichabod's interest in Katrina by using practical jokes rather than engaging in physical violence. Although Brom is confident he could win a fight, he is wary of Ichabod's social status and community leadership, which could make Brom appear as a bully. Brom, characterized by mischief more than malice, opts for pranks to undermine Ichabod without causing real harm.

Brom Bones feels triumphant after Ichabod disappears, as he quickly marries Katrina Van Tassel, whom Ichabod also admired. Brom's knowing look and laughter when people mention the smashed pumpkin suggest he may have been involved in Ichabod's disappearance. If Brom was indeed the "headless horseman," he likely feels victorious for scaring away his rival and winning Katrina's affection, reinforcing suspicions about his possible role in Ichabod's fate.

Brom Van Brunt is nicknamed "Brom Bones" due to his Herculean frame and strength, contrasting with Ichabod Crane's frailness. His nickname highlights his physical prowess and solid nature, opposed to Crane's delicate and bookish demeanor. Brom resembles modern characters like superheroes or Mr. Incredible from The Incredibles, known for strength and good nature. Brom's American hero archetype represents robust, pragmatic qualities versus the more effete European characteristics embodied by Crane.

In Washington Irving's "The Legend of Sleepy Hollow," Brom Bones, also known as Abraham Van Brunt, is portrayed as a strong, broad-shouldered man with curly black hair, embodying a robust and athletic persona. He is sociable, often accompanied by a "gang," and acts as an umpire in disputes. Initially depicted as more brawn than brain, Brom demonstrates cleverness by possibly disguising himself as the Headless Horseman to scare Ichabod Crane away, showcasing some character development.

Katrina Van Tassel is known for her beauty and "vast expectations." Her attire reflects these qualities by combining ancient and modern fashions, showcasing her beauty and wealth. She wears antique gold jewelry, linking her to her family's heritage and wealth, and a stylish "stomacher." Her provocatively short petticoat highlights her shapely ankles and feet, underscoring her flirtatious nature and the expectation of attracting suitors who can match her social standing.

In "The Legend of Sleepy Hollow," Brom Bones impersonates the Headless Horseman by carrying a pumpkin, which he holds as if it were his head. Bones throws the pumpkin at Ichabod Crane during their chase.

The Headless Horseman in "The Legend of Sleepy Hollow" is a legendary figure believed to be the ghost of a Hessian soldier who lost his head to a cannonball during the Revolutionary War. His primary motivation is to search for his missing head, and he is said to ride nightly, haunting the area around Sleepy Hollow in pursuit of this goal.