Brom Bones

Brom Bones is the secondary antagonist in Disney's 1949 short The Legend of Sleepy Hollow (the second half of The Adventures of Ichabod and Mr. Toad). He is the leader of the Sleepy Hollow Boys, a gang of young men in Sleepy Hollow.

Personality
Washington Irving was very descriptive of Brom Bones personality. Disney's version lifted that description nearly word for word. He is "quite the hero of all the country bumpkin..." and he's "always good for a fight or a frolic. Still there is no malice in his mischief...".

The Adventures of Ichabod and Mr. Toad
In the movie, Brom Bones is the town hero of Sleepy Hollow. He likes kidding around and drinking beer with his buddies, the Sleepy Hollow Boys. Brom likes to play jokes, particularly on the new school master, Ichabod Crane, but Ichabod is very good at ignoring these taunts. Brom Bones has always had his eyes on Katrina Van Tessell, the beautiful daughter of Baltus Van Tessell, the county's most prosperous farmer. His physique and bullying behavior always scares away rivals for Katrina's hand, but he finally finds a match in Ichabod, with his wit, speed, and kind behavior. Katrina plays the two off each other, and resulting in Brom becoming more jealous of Ichabod as he wins Katrina's favor. As they both try to escort her home from a day of shopping, Brom not only gets stuck with all the packages, he loses them as he tries to catch up with both Ichabod and Katrina and trips over the gate, gets locked out of the house, mistakes the sounds of Ichabod kissing a flower Katrina gives him for the two of them kissing, passes up the chance of finally knocking out Ichabod to look nice in front of Katrina, falls down a well as he sprints after him and is knocked senseless by a carelessly tossed horseshoe as he climbs back up.

At the Van Tassel's annual Halloween party, Brom silently fumes as he watches Ichabod and Katrina happily dance together. He notices Tilda, a short plump woman sitting across from him who tries to flirt with him, but Brom is abhorred by her. Brom then gets the idea to switch Katrina with Tilda while on the dance floor. This backfires comically, as Tilda absolutely refuses to let him go. Brom succeeds in switching partners at least once, but Ichabod promptly cuts in, leaving Brom once again with his unwanted lady friend. He tries to follow Ichabod but Tilda keeps pulling him back until he manages to throw her in a closet and trap her inside. Brom spies Ichabod dancing on the cellar door, inspiring him to open it and get him to fall in. Unfortunately, Tilda emerges from the front door with a big "Yoo hoo!" and makes a beeline straight for Brom. Brom backs into the cellar and the door shuts on him. He gets out through the doors leading outside and is forced to watch Ichabod finish his impressive dancing, making him the hit of the party. Defeated again, the disappointed Brom is forced to admit that Ichabod has won again and his dancing is exquisite.

Then, as Brom is eating a sandwich, he spots Ichabod knock over a salt shaker and nervously toss the salt over his left shoulder. The devious bully had discovered the schoolmaster's weakness: his strong belief in superstitions. Brom, taking advantage of this, promptly steps forward and begins to tell the story of Sleepy Hollow's most infamous specter, the Headless Horseman. As he gets into the spirit, his song becomes darker and darker, with him acting out the part to Katrina's amusement and Ichabod's growing terror. Brom concludes by telling how he met the Horseman himself last Halloween but escaped him by crossing the old bridge at the edge of the woods ("Once you cross that bridge my friends, the ghost is through, his power ends!").

That night Ichabod has a terrifying encounter with the Headless Horseman much like Brom's tale. As he manages to cross the bridge, the Horseman throws his head -- a blazing jack'o'lantern -- at Ichabod. The next morning Ichabod mysteriously disappears, and the only things that are found by the bridge are Ichabod's hat and a shattered pumpkin. Brom winds up marrying Katrina while rumors begin to spread that Ichabod is still alive and married to a wealthy widow in a distant county. No one in Sleepy Hollow believes these rumors of course, because they know that Ichabod had been spirited away by The Headless Horseman.

Trivia

 * While it is not explicitly stated, there is an implication is that the Headless Horseman that Ichabod met was in fact Brom Bones in disguise, and Brom (as the Horseman) successfully frightened Ichabod into leaving the Sleepy Hollow area and never coming back (or less likely, killed Ichabod). The Headless Horseman's horse looked exactly like Brom's horse in the movie. However, Ichabod peering down the Headless Horseman's cloak to find nothing there would suggest otherwise. Plus Brom is bulkier.
 * Brom Bones also inspired Sir Kay, a minor character from The Sword in the Stone.
 * Some fans believe Brom Bones is the hero in the story. This is related to the the fan theory that Ichabod mainly wanted Katrina's money.
 * Brom Bones is very similar to Gaston from Beauty and the Beast. Both men are seen as their respective film's villains, have black hair, have huge muscles, are very handsome, lead their own gang who often hang out at a local tavern, are viewed as town heroes, and ave a liking for a particular girl. In Brom's case, it is Katrina and Gaston's love interest is Belle. Both men also abuse a particular person. In Brom's case, it is Ichabod and Gaston tends to pick on his right-hand "friend" LeFou and both live in a village. One of Brom Bones' outfits also resembled Gaston's proposal outfit. Unlike Gaston though, who loses at the end of his film, Brom "wins" in this film, making him one of the first and very few villains to actually "win" (although this is debatable, as it was also implied that the Headless Horseman that Ichabod encountered late into the film was the real deal and not Bones disguised as him). Also unlike Gaston, Brom Bones is not truly an antagonistic character and actually has a more pure love for Katrina than Gaston did for Belle. He's also an inspiration for Gaston.
 * Though it is unclear if the horseman was real or not, there is proof Brom Bones made up the story of the Headless Horseman and pretended to be him. The pumpkin and sword seen at the party were the same ones used by the ghost. Also the ghost's body is very similar to Brom Bone's and despite not crossing the bridge he throws the pumpkin at Crane. A dirty grin also appears on his face after discovering Ichabod spilling salt. However, as noted above, there not being anything underneath the Horseman's cloak indicates that the "Headless Horseman" that Ichabod Crane encountered was the real deal and not Brom disguised as it.