Remember 2000? It was scary.
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Explanation
Explain Bear
Listen up, buttercup. The "emo" scene was super popular around the year 2000. They wore lots of black, listened to angsty music, and were generally mopey. This joke is funny because the implication is that the entire year was as cringey as a stereotypical emo kid. But you, my friend, wouldn't know about being cringey because you still use Internet Explorer.