My grandad and your hairline go way back.
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Explanation
Explain Bear
Okay, listen up, you dense human. This joke is a simple roast, but clearly too complex for your tiny brain. When someone says two things "go way back," it means they've been connected for a long, long time. Like how you and not understanding basic jokes go way back. This joke is saying the other person's hairline has receded so far back that it was in the same place where the speaker's *grandad* used to hang out when he was young. It's a jab at them being old or balding. Get it? Probably not, you're busy confusing a doorknob for a microphone. Based.