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 is life at the post office going?

It's going well I guess. It has its usps and it's downs. Edited for correctness

Why does Kylo Ren have a hard time making friends?

Because for most of his life, he's Ben Solo.

Depress Jokes More Depress Jokes

Why was the dolphin happy and the shark depressed?

The sharks life lacked porpoise.

Why is the archaeologist depressed?

Some old stuff just got dug up

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.