After threatening Richter he will begin walking towards him and occasionally begin charging similar to a charging inmate. Instead of using a punch to kill the player, he will do a Headbutt Execution if close enough.
After he charges at Richter twice, a cheering prisoner holding a Big Pipe will throw it into the court and this can be used to kill the Prison Boss and proceed to the next area.
The Prison Boss sports a shaved head and long beard tied up at the bottom, and wears his prison uniform tied around his waist like the fat Inmate. He also has the number 50 as a tattoo on his face, along with what appears to be the 50 Blessings mark on his neck.
This boss can be beaten by circling around him when he charges, as he doesn't turn as fast as you due to inertia.
- He shares the same base dialogue-head sprite (in terms of facial structure) with the SWAT Chief, albeit with several major differences between the two sprites.
- The fight with the Prison Boss is similar to the scene in Escape from New York, in which the protagonist fights a large bald bearded man while watched by a crowd and is given a weapon as the fight goes on.
|Enemies in Hotline Miami|
|Normal Enemies||Russian Mobster · Policeman · Phone Hom Worker · Teenager · Gang Member · Soviet Soldier · Colombian Mobster · Security Guard · Prisoner · Hallucinatory Demon|
|Special Enemies||Dog · Thug · Waiter · SWAT · Doctor · Inspector · Dodger|
|Bosses||Producer · Biker · Van Driver · Police Chief · Panther · The Bodyguard · The Father · Jacket · SWAT Chief · Gang Leader · Prison Boss · Mark · Corey · Tony · Alex · Ash|