One of April's old toys that she brought with her to Newport when she left home. Constable Guybrush is "part man, part ape - in addition to being an officer of the law, of course". When the key in his back is wound up, Constable Guybrush sings 'Do the Monkey' and plays the cymbals he carries. Unfortunately one of his eyes has come loose over time, though as April discovers, it does come in handy later on. She also uses Constable Guybrush in the alleyway behind the Mercury Theatre to fool Freddie Mellon into thinking Frank Minelli is there, waiting to take revenge for Freddie chasing him down Metro Circle with a broom. If the eye is not removed after the first shift, it can be re-obtained by returning to the alleyway, allowing the toy to be carried with April for the remainder of the game (though it serves no further purpose).
The name 'Constable Guybrush' is a clear homage to the character Guybrush Threepwood from the Monkey Island games. April also whispers that Constable Guybrush "doesn't much like being called 'monkey' ", which refers to the Librarian from the Discworld novels. He was turned into an orang-utan and is usually quite affable, unless anyone is stupid enough to use the word 'monkey' in his presence.
Obtained from the bottom of April's closet.