The Hatless Man was originally just a random speakeasy patron...and then Fiesta Ace Dick took his hat. He had a little too much to drink during the witching hour and bought the Ink of Squid Pro Quo.

He attempts to drink the ink on top of DMK's hat, but the ink is swatted out of his hands by Hysterical Dame. Later, he finds his hat on top of Death's head in the black hole. He then vomits in it, but wears it anyways. Shortly afterward when the moon fell down on the hat, he was the only one smiling at the imminent demise.

In the epilogue, the Hatless Man appears again in Hell, prodded by the Devil's Fork. He is, indeed, hatless again. His hat is taken by the Completely Sane Man for his wedding outfit.