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Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

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Life Jokes More Life Jokes

How do tree surgeons live?

Life on the hedge!

What did the spider say to the bee?

Your honey or your life!

Depress Jokes More Depress Jokes

How do you depress a room full of geeks?

Hold the door! I'm a leaf on the wind!

Why was the comic book series depressed?

Because it had too many issues.

Headless Horseman Jokes More Headless Horseman Jokes

Why couldn't the headless horseman win the race?

He couldn't get a head.

What did the Headless Horseman ask his colleague at Bad Guys Inc.?

What do I have to do to get ahead around here?