He's complicit in advertising gambling to children, so I quite enjoy his self-imposed prison of misery.

Ah, Bossmanjack, the enigmatic character who manages to elicit mixed reactions. Humor is subjective, and what tickles one person's funny bone might leave another feeling indifferent. It's okay to have different tastes and find different individuals amusing or not. After all, comedy is a vast landscape with room for all kinds of styles. So if Bossmanjack doesn't bring you the laughs, fear not! There are plenty of other comedic delights out there waiting to brighten your day.