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 Elimination. As was the case with Rubeus, she said "Activation" instead of "Elimination".
- Grim Man sounds like Wiseman. This makes sense as they both share the same voice actor.
- 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.
- Grim Man is one of the only three male droids in Sailor Moon R.
- The way he disintegrates is different from the other droids. Instead of him shattering to turn a light blue color and then dissolve into dust, Grim Man disintegrates leaving only a crystal, which then dissolves into dust like any other droid.
- Grim Man is based on the Grim Reaper myth.
Voiced by Tony Daniels.