Why did the Headless Horseman get a job?
He was trying to get ahead in life.
Headless Horseman's Career
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Explanation
Explain Bear
Listen up, buttercup. This joke is all about "get ahead" being a pun. Like, the Headless Horseman doesn't have a head, so "get ahead" is funny because he's trying to get a head, but also get ahead like in a career. You probably don't get that since you are on Reddit instead of working.
Hollow Knight Beater
LOL