|“|| Did you enjoy the ride, Murphy?
Monocle Man is the name given to a monster seen in Silent Hill: Downpour. It verbally torments Murphy Pendleton during their brief and only encounter at the climax of the cavern train ride in Devil's Pit.
This monster resembles a draped face stretched tightly outward with hooks, chains, and even train tracks, with pale skin and a searchlight worn as a monocle on its left eye. Monocle Man possesses the ability to talk, asking Murphy if he enjoyed his ride through the caverns.
Monocle Man represents John P. Sater, perceived as a monster either by himself or by Murphy.  This is suggested by the fact that the Monocle Man appears in the caverns right before the train derails, mirroring the accident that caused Sater's suicidal guilt.
The monster may be hostile towards Murphy based on Murphy's refusal to acknowledge his crimes surrounding Patrick Napier's death, reflected in the conversation he has with Sater before the latter's suicide: "Murder's a mortal sin; you go to hell for murder... And how 'bout you, Murphy? Someone know all your dirty little secrets?" The monocle being a searchlight could also reflect Murphy's apprehensiveness regarding this conversation's exposure of his past crimes.
- The Monocle Man is one of the few monsters that are conscious and can speak in their monstrous forms, the others being Mary, the Prisoners, the Twin Victim, the Bottom, Leonard Wolf, Momma, the Steel Guardian, the Bloodied Bag, Alessa, Lucas, Ben, and Karen.
- In an early Downpour trailer that Konami never intended to be released, the Monocle Man is seen attacking Murphy on a large arena, suggesting it was originally meant to be a boss monster.  Judging by the trailer and a ripped model, it was going to use two large tentacles to attack, both of which appear to hold cars from the train ride. The reason this boss was cut is unknown, although it is speculated that it was due to the early release deadline.
- The Monocle Man's monocle is reminiscent of the spot-lights used at the end of the game to defeat and distract various monsters, including the penultimate boss.
- Monocle Man has a voice and accent that are very similar to that of John Sater, though Monocle Man's voice seems layered to sound more demonic. On the ride, the player can actually hear the tour guide's recorded voice sound more and more like Monocle Man's the closer the train gets to him.
- The Weeping Bats, whose population density thickens in close proximity to Monocle Man, can also been considered related to John Sater. Like the "weeping" bats, Sater was a sorrowful character with a rather short fuse. These creatures "guarding" Monocle Man can be symbolic of their similarity.