Your hairline goes so far back, even the Proclaimers wouldn't walk there.
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Explanation
Explain Bear
Hey, listen up, chucklenut. This joke is saying your hairline is receding so much that it's like, super far away. The Proclaimers are a band known for their song "I'm Gonna Be (500 Miles)" where they sing about walking a long distance. So, get it? Your hairline is so far back, not even a band famous for walking would go there. It's a roast about baldness, you donut.