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?

I've Got a Whole Latte Jokes

I've Got a Whole Latte 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.