Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

Previous Random Joke Next
Life Jokes More Life Jokes

What do you call a dinosaur that raps about life?

A philosorapper

Why did the hearing aid saleman give it up for a life of piracy?

A: Because he only made a good buccaneer.

Depress Jokes More Depress Jokes

Why was the diamond depressed?

He had been under a lot of pressure lately.

What does a guy with no friends be for Halloween?

Depressed

Headless Horseman Jokes More Headless Horseman Jokes

Why was the Headless Horseman depressed?

He could never seem to get ahead in life.

What did the Headless Horseman ask his colleague at Bad Guys Inc.?

What do I have to do to get ahead around here?