Why couldn't the headless horseman win the race?

He couldn't get a head.

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Win Jokes More Win Jokes

Why won't Bernie Sanders win the rational election?

Because he's two radical.

Why has /r/jokes won an environmental award?

Everything gets recycled.

Race Jokes More Race Jokes

Why couldn't the headless horseman win the race?

He couldn't get a head.

What does a Persistent Jedi do when he gets destroyed in a race?

An all day run

Head Jokes More Head Jokes

How can you tell if a shark has dandruff?

He left his head and shoulders on the beach.

What do you call a bloke with a bus on his head?

Dead.

Headless Horseman Jokes More Headless Horseman Jokes

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

Why couldn't the headless horseman win the race?

He couldn't get a head.