- Acting for Two: Along with their regular roles, Greg Lee, Lynne Thigpen and the members of Rockapella all appeared as different informants, with Greg's and Lynne's characters being pre-taped and appearing on the monitor.
- The Cast Showoff: Rockapella did this every episode, obviously. We also got to enjoy Lynne Thigpen's singing talents whenever she served as the "Acmettes", or when we saw footage of some of her earlier work.
- Missing Episode: "Auld Lang Gone" (Season 2), which went unaired because the winning gumshoe fell and suffered an arm fracture on the Europe map. Sure, they got the runner-up to take her place (and he won, meaning they both got the trip), but it remains an Old Shame for WGBH Boston and WQED Pittsburgh, the stations that produced the show. It's especially regrettable as the episode featured a guest appearance from none other than Gene Wilder.
- There were other issues as well, Such as Sean ripping Greg Lee's jacket, The Plastic Diver Guy's tank broke down, etc. Also, Lynne Thigpen had a sore throat at this time. So Greg Lee took over as the substitute chief and Double Dare (1986) host Marc Summers took over as a guest host.
- Screwed by the Lawyers: In 2009, Warner Music Group (WMG) claimed the theme song on YouTube. And many uploaders of Where in the World is Carmen Sandiego? were banned from YouTube because of that.
- Star-Making Role: Before this show, Rockapella was just another college a cappella group. Now everyone thinks of them whenever someone brings up the style.
- Throw It In!:
- Most of Rockapella's sound effects. Many of their antics were built around this.
- In one bonus round, the kid was on his last country, with not quite enough time to run to the country, so he dived - and broke the siren off the pole it was mounted on. The producers not only decided to count it as a win, but let him keep the broken siren as a souvenir in addition to all the other prizes.
Trivia / Where in the World Is Carmen Sandiego?