Anti-Climax Boss: Many enemies are this, considering how simplistic the combat is. Notable examples include the sheriff himself at the end of his questline as well as a snow bear that Crossley asks Joe to kill.
Why does the mob suddenly have its stuff all set up right near Joe's house?
Why does no one care when Joe murders people in public, except for the police?
How is Joe able to take down enemies of all kinds, with only his fists? This includes the sheriff, various criminals armed with knives, bears, by the way.
Narm: Many scenes are hard to take seriously with the cartoonish artstyle. Keep in mind that this series also gets very dark, involving things such as murder, cannibalism, and generally ruining people's lives. All with blocky bodies and items.
The player's family can be this, considering that they're quite clingy and always need Joe around, even when he already spends enough time with them as is. It can be hard to keep their happiness meters filled, especially when the player is trying to focus on money.
The player's best friend fits into this category quite well. He's unreliable, gets the player into trouble, and his death ends up kickstarting the entire plot. Doesn't help that even Joe doesn't really care about his death after it happens and doesn't bring up his best friend much. As a result, the best friend's wife also fits here by being connected to him.
The Woobie: Lucy Lane can end up being this if Joe performs surgery on her and makes her a mess of a human being. All to get Star some more followers.