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 did Earth say to the Sun?

My life revolves around you!

What do you call someone who isn't a redhead but colors there hair red later in life?

A trans-ginger

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How does a pair of pants feel when it is ironed?

A: Depressed.

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

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.