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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

What is twitter?

3. Twitter is beautiful. 4. What is life

What's on a gangster artist's t-shirt?

Still Life.

Depress Jokes More Depress Jokes

Why was the diamond depressed?

He had been under a lot of pressure lately.

Why was the calendar depressed?

His days were numbered.

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?