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 do you call a wizard with a good outlook on life?

An Opti-Mystic.

Why didn't the astronauts land on the moon?

Because it was full. * (from a taffy taffy wrapper--oh my god what am I doing with my 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 is the archaeologist depressed?

Some old stuff just got dug up

Headless Horseman Jokes More Headless Horseman Jokes

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

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

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.