Even allegedly smart people can make life-changing blunders that seem very, very obvious in retrospect.
What did web browsers look like 20 years ago, and what kind of crazy features did they have?
Push the Button!
Scenes from Half-Life 2:Episode 2, showing Gordon Freeman being a jerk.
Lost Laughs in Leisure Suit Larry
Why was this classic adventure game so funny in the 80's, and why did it stop being funny?
In Defense of Crunch
Crunch-mode game development isn't good, but sometimes it happens for good reasons.