25. How the West Was Fun (1994)
Far and away, this is the worst title out of the dozen or so films the Olsen twins churned out in the '90s and early 2000s. It was a close race between How the West Was Fun, Double, Double, Toil and Trouble, and Billboard Dad, but ultimately, this takes the prize.
The sin: a miserable, miserable pun. You might be thinking, "They were just kids making movies for kids." But remember that these films served as the seed money for their billion-dollar fashion empire. There are likely many embarrassing childhoods out there that were far less profitable.