A Tricky Monkey, true to its name, is a monkey-like creature with dark grey skin. It has small ears that are black on the inside, as well as two large, jagged horns on its head. Its face is pitch-black with glowing yellow eyes. It wears a high-collared, slightly tattered, purple coat with white cuffs and thin, white lines decorating its collar. It holds two gold, diamond-shaped cymbals in its hands, and its Heartless emblem is printed on the front of its coat.
The Tricky Monkey's name and appearance refer to cymbal monkey toys, which it resembles. The "tricky" half of its name may refer it its ability to disguise itself as a treasure chest.
The Tricky Monkey has the ability to fire three music note-like projectiles, which reverse the player's direction for a period of time if hit. The treasure chests that it hides in are the only treasure chests seen in Mission Mode, thus making them easy to avoid.
However, if it is summoned, it'll immediately fire the projectiles, which can be deflected back and deal high damage to itself.