Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

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Life Jokes More Life Jokes

When does a cup stop being a cup and start being a mug?

When it gets a handle on life.

Why don't we wait for life on other planets to find us?

Why do we have to do all the work

Depress Jokes More Depress Jokes

How do you depress a room full of geeks?

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

What kind of car does depressed Daniel drive?

Sad Dan

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 couldn't the headless horseman win the race?

He couldn't get a head.