Why couldn't the headless horseman win the race?

He couldn't get a head.

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Win Jokes More Win Jokes

What's a metaphor?

Winning the game tournament!

What do cubs fans do after they win the world series?

They turn off their Xbox.

Race Jokes More Race Jokes

What's difference between Jesse Owens and Adolf Hilter?

Owens can finish a race.

What did the communist say at the beginning of the race?

On your Marx, get set, go!"

Head Jokes More Head Jokes

Where do you think you're going at this hour?

gun hangs head & turns around

What foreplay does the praying mantis girlfriend enjoys ?

Being given head.

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.