Bossmans are enemies that are found in the Underworld and Stone Pit levels but they also appear at Loony Park in Painkiller: Overdose and High Seas in Painkiller: Resurrection. There are 2 versions of them.
The Red Bossman is the first bossman enemy you will ever meet. He is one of the pirates who didn't lose his flesh. Also his clothes are very similar to the Red Pirate's suggesting that he was also a guard because of its movement nature being only standing in place or moving in a specific spot and also the fact that he spawns with the Red Pirates. He is holding 2 cannons in his both hands which will shot 2 cannon balls at you. They act similar to the Bolt Gun's bombs but these ones are bigger.
The Yellow Bossman is the second bossman enemy you will ever meet. He is also one of the pirates who didn't lose his flesh. Also his clothes are very similar to the Yellow Pirate's suggesting that he was also a member of the crew because of the fact that he spawns with the Yellow Pirates. He is holding one single cannon in his both hands which will shot one cannon ball at your location. The cannon ball cannot be seen so it will always hit its target if he stays too long in the same place.
- These enemies were likely going to appear in the unreleased Galleon level and were probably carried over to Underworld and Stone Pit as returning enemies.