The Headboys wear black leather jackets with a symbol of two bloody folding knives on the back. They also wear police helmets.
Events of We Happy Few Edit
Act One Edit
One of the first tasks that Arthur is given is to retrieve some war medals stolen by the Headboys. Arthur goes into their "fortress" through the back door, but gets captured and is forced to fight in their arena. After winning the fight against the first opponent (Danny Defoe), Arthur fights two more contestants before being let out, in which he is dumped into a room full of bodies. He is forced to sneak (and fight) his way out, along with collecting the medals and a Power Cell.
Later, when approaching the Train Station, Arthur sees some Headboys arguing with a strange bald man (Ollie Starkey), who is supposedly hoarding all of the Victory Meat. He chucks bottles down at them before they use explosives to break into the building. Arthur later fights some more Headboys while attempting to enter the Cathedral via the old train station. After this, they can be randomly encountered in the Garden District.
Act Two Edit
While having little to no impact on Sally's campaign, the Headboys can be randomly encountered in the Garden District by her.
Act Three Edit
At the beginning of Ollie's story, the Headboys begin to bomb the Train Station shortly after Arthur and Ollie bid each other farewell. They have acquired a large quantity of explosives after having captured and interrogated a soldier from the Home Army. Ollie kills many of them before having to escape the Train Station using a parachute, all while it is collapsing. Ollie then goes to break out the soldier, facing even more Headboys. From there, they can be randomly encountered in the Garden District.