- "Oh goodie, this should be a scream. Your scream!"
- —Grim Man, Ep. #68
The Grim Man is a droid that Prince Diamond sends to capture Rini. He has the appearance of a hooded cloaked figure (though he looks slightly different from Wiseman) and uses a scythe. He appeared in Sailor Moon R Episode 28, The Secret of the Luna Sphere.
Diamond sent Grim Man into Rini's dreams to keep her asleep until he could capture her. Sailor Pluto contacted the Sailor Scouts from the future through the Luna Sphere and transported them into Rini's dream world where the Sailor Scouts fought the Grim Man. None of the Sailor Scouts could even damage the Grim Man, until Sailor Moon, after saving Rini from falling to her death, attacked the Grim Man with her scepter, and then destroyed him with Moon Scepter Activation.
- The Grim Man attacks Rini inside the dream world. This is similar to an iconic horror movie villain, Freddy Krueger from A Nightmare on Elm Street, but his overall look is based on the Grim Reaper myth.
- The Grim Man is one of only three male Droids used by the Negamoon.
- The way he disintegrates is different from the other droids. Instead of outer layer shattering then turning into dust, the Grim Man disintegrates leaving only a piece of Dark Crystal, which then dissolves into dust. This makes him a very unique Droid.