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

All Aboard

The brilliance of this joke is its brutal simplicity. “I lost people along the way” sounds reflective, almost poetic — until the punchline crashes in with the force of, well, a train. Turns out, he was a terrible tour guide… or maybe just a very literal one.

There’s a dry humor to this one that hits harder the second time you read it. It’s dark, yes, but also wonderfully absurd. Only a dad could deliver that kind of deadpan twist and turn it into a life lesson: maybe your job isn’t the problem — your sense of direction is.