Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

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Life Jokes More Life Jokes

What is the one riddle that everyone gives up?

The riddle of life!

How do tree surgeons live?

Life on the hedge!

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 dolphin keeper depressed?

Because he had no porpoise.

Headless Horseman Jokes More Headless Horseman Jokes

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

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

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