Hustler's Hallmark

“

Oh they’re gonna find ya all dead in the alley, with cats lickin’ at ch’ya! Click to listen — The Demoman

”

The Hustler’s Hallmark, or Pimp hat, as it is often referred to, is a community-created headwear item for the Demoman and was chosen by Valve to be released with the first wave of community-contributed content due to its outstanding quality. It appears as a wide-rimmed hat with a feather sticking out of the side, held by a flannel band.

Trivia

• This hat is commonly referred to in-game as "The Pimp Hat."
• In keeping with the Demoman’s other Blaxploitation themed hat, the Hallmark bears a strong resemblance to stereotypical pimp hats.
• The Hallmark is one of the few hats that is jiggleboned, meaning that it will jiggle realistically as the player moves around. Namely, the feather is what jiggles around.
• It could be said that the Hallmark has also been influenced by Juan Sánchez Villa-Lobos Ramírez’s (Sean Connery) Hat from the Film Highlander. This would make sense as one the Demoman’s weapon unlocks is called the "Eyelander" and both hats look similar, even down to the stripe that is on both hats.