Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

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Life Jokes More Life Jokes

How long does it take to reach the ground from 110 stories up?

The rest of your life.

What's the best moment of your life?

me: That time I won a stuffed dino- wife: That didn't involve a dinosaur me: Our wedding

Depress Jokes More Depress Jokes

Why is depressed clothing so convenient?

It hangs itself

Why was the dolphin keeper depressed?

Because he had no porpoise.

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.