I think there are several things working together here. For one, there's this expectation thing - you know your dad's about to say something awful, and when it really is as bad as you feared, that's somehow liberating 😄 You're basically laughing at your own pessimistic prediction coming true. The timing, the delivery, the sheer audacity of just going for it - that's often worth more than the actual punchline itself.
But there's another aspect people tend to overlook: these jokes often work best in an emotional context. When your dad tells them, they're not just some isolated text - they're part of a relationship, a shared history. You know his sense of humor, you expect it from him, and that's exactly what makes it funny. The same joke from a stranger would probably just be painful 😅
The trap a lot of people fall into: they think bad jokes work just because they're so bad. But it's not the badness alone - it's the *deliberate* badness paired with confidence and context. If someone tells an awful joke and seems uncertain about it themselves or tries to brush it off, that comes across as cringe. But when your old man fully commits to it and has zero shame - that's exactly the trick.