Carmen Sandiego/YMMV

Alternate Character Interpretation: One potential explanation for the Good Guides' apparent Idiot Ball in "Great Chase through Time" is that sometimes they know just where the thieves are at, but they want you to figure it out. Especially prevalent in 1808, since Renee Sance should have spotted the sousaphone right off the bat, Course, this doesn't excuse the Idiot Ball of the people in said-timeframe not spotting the thieves themselves. (Honestly Edison? Dee Cryption was RIGHT THERE IN FRONT OF YOU.)
Crack Pairing: Carmen and Waldo.[1] Less often but Carmen and a younger Ms. Valerie Frizzle [2].
Evil Is Sexy: Let's face it, Carmen is hot.
It Was His Sled: Carmen Sandiego was once an ACME detective.
Memetic Badass: Carmen can steal anything. Anything.
Memetic Mutation: Circa 1990s or so, everyone knew that Carmen Sandiego could steal anything, even if they had no familiarity with the games themselves. As a result, she's also likely the Trope Codifier for Impossible Thief.
Older Than They Think: News about Jennifer Lopez's involvement in a potential Carmen Sandiego movie can be traced as far back as 1999.
That One Level: 1492 in Great Chase Through Time. You have to sail all the way across the Atlantic ocean tile by tile and repeatedly click on it. Think that's annoying enough? Well Rock Solid announces what direction you're heading in every time you move, and you hear that annoying ship bell every time.

"We're now aiming toward the wild, wild west!"

- 1776 also deserves a mention.
- If you are tone deaf -- Hollywood or otherwise, Beethoven's era is a pain in the ear. Music pun totally intended.
  - But if you remember Fantasia, the Pastoral part will at least be a bit easier.
- The ending. You chase her through all the places you've been before. Good luck figuring out where to go next.
  - Although it's actually fixed, not randomized, and you can Take Your Time all you want - and they usually give you some good clues about where she went. If anything, this was a Final Exam Boss