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 does Mexico never win the Olympics?

Because anyone who can run, jump, or swim already left.

How do you congratulate a fighter after winning a match?

Good jab.

Race Jokes More Race Jokes

Who won the race?

Society.

Why can't mites race in NASCAR?

Because mites make rights, not lefts.

Head Jokes More Head Jokes

How do you know Kurt Cobain didn't have dandruff?

A bit of his head and shoulders were found behind the couch.

What's the difference between spit and swallow?

A firm grip on the back of her head.

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 was the Headless Horseman depressed?

He could never seem to get ahead in life.