Who Needs a Comedy Special When You Have These Boomer Dad Jokes?

World’s Worst Tour Guide

At first, it sounds deep: remembering everyone you’ve lost. But then — bam! The punchline spins it all into comedy: maybe tour guiding wasn’t the best career. The delivery is everything, transforming something heavy into laugh-out-loud dark humor.

This joke works because it plays on self-deprecation and subverted expectations. It’s bold, clever, and perfectly timed. And while he may not be cut out for leading city tours, this dad might just have a future in stand-up. After all, if you’re going to get lost, you might as well laugh doing it.