Whether you first heard it on the playground, from that one eccentric uncle at family gatherings, or through books, movies, or TV shows, almost everyone can recall a riddle that had them scratching their heads for days. Some are lighthearted classics with simple yet clever answers, like the infamous “cement room” riddle. Others are mind-bending logic puzzles that still leave us baffled—like the tricky “12 men on an island” riddle featured in Brooklyn Nine-Nine. No matter the difficulty, these brain teasers have a way of making us feel both nostalgic and utterly clueless.

Take a look at these classic riddles that have perplexed people over the years. Which ones had you completely stumped when you first heard them? And if you still can’t figure out the answer, don’t worry—you’re not alone!

1. The Case of the Two Masked Men

Submitted by Facebook commenter Juan Crespo

Riddle: A man leaves home on foot one evening, makes three left turns, and arrives back home—only to find two masked men waiting for him. Who are they?

Answer: The catcher and the umpire. The man hit a home run in a baseball game!

If you didn’t immediately get this one, don’t feel bad—many people struggle with the sports-related twist. It’s one of those riddles that seems completely unrelated to its answer until you put the pieces together.

2. The Mysterious Cabin in the Woods

Submitted by Facebook commenter Matt Bishop

Riddle: There’s a cabin deep in the woods. No footprints can be seen around it. Inside, there are seven people, all dead. They all died at the same time. No one else is in the cabin. How did they die?

Answer: It’s an airplane cabin—the plane crashed in the woods.

This one is a perfect example of how wording can completely throw you off. When most people hear “cabin,” they immediately picture a log cabin, not an airplane cabin. The key to solving this riddle is thinking outside the box—literally!

These are just a couple of the riddles that have confused and entertained people for years. Some of them rely on clever wordplay, while others require lateral thinking. No matter the approach, they all have one thing in common: they make you think twice.

Which of these riddles stumped you the most? And do you know any others that have left people scratching their heads? Let us know!