Jack Rider is the special boss for the Halloween update to SAO. In comparison to the other special bosses, Jack Rider is the deadliest. His appearance is a muscular man in black clothing, and riding a black steed with glowing red eyes. As obvious appearance goes, he is headless. His head is strictly a glowing pumpkin with a menacing facial expression cut into it.
To emphasize the boss's threat level, a new location has been added to the game. The Hollowed Forest is a section of the Arglades Forest (on Floor 25) where the life has been drained from the landscape. The trees are rotted inside and out, and all signs of green, vibrant life disappears completely. The only way to summon Jack Rider, and fight him, is by traveling to a foggy clearing and lighting a carved pumpkin on fire. The pumpkin's carved face with come alive and laugh as the horse and its headless rider emerges from the ground. The rider will then take the pumpkin and activate the battle.
Its attacks are mostly close ranged, however, it is able to throw exploding pumpkins. These pumpkins can also be summoned as minions to help fight the player(s). The minions are easy to defeat (as easy as a Frenzy Boar) and only have a single attack of launching small blobs of fire from their lit mouths.
Reward for killing this boss include:
- Completion of special quest: "The Headless Horseman".
- Exploding pumpkin bombs (Irreplaceable item. 20 bombs dealing 1000 damage each. Cannot replenish supply)