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 something that can breakdance on the floor only once on their life?

A fish

What is life like for a wood worm ?

Boring !

Depress Jokes More Depress Jokes

Why was the dolphin happy and the shark depressed?

The sharks life lacked porpoise.

Why was the diamond depressed?

He had been under a lot of pressure lately.

Headless Horseman Jokes More Headless Horseman Jokes

Why couldn't the headless horseman win the race?

He couldn't get a head.

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.