Of course, the 1985 version was made before the Hole in Flag revolutions, so it features the Soviet Union still being a country, etc. The 1992 deluxe edition has a reunited Germany alongside an existent Soviet Union, the game having fallen victim to the same period of short map shelf life as the game show's first season. The 1994 revamped version of the '92 game was the first to feature Russia instead of the Soviet Union.
While the 1996 version came out late enough to have cleared the end of the Cold War, it was nonetheless caught off guard by the fall of Zaire. In the 1998 revamped version of that game, the Democratic Republic of the Congo is still called "Zaire" for the most part, but its entry in the in-game database has been rewritten so that it awkwardly explains that "Zaire" is now technically the country's former name.
All three versions give population statistics that are, of course, outdated now.
All three versions predate the introduction of the euro, so they're all dated when they give as a clue the name of a European currency that has since been replaced by the euro.
In the 1996 version, your location for Afghanistan is one of the Bamiyan Buddha statues, both of which were dynamited by the Taliban in 2001.note Incidentally, Afghanistan's flag in the in-game database is that of the pre-Taliban government, which was undoubtedly still in power when the game was in development. Around the time of the game's release in 1996, the Taliban took over, and the previous regime became the Northern Alliance resistance. However, the Northern Alliance continued to be internationally recognized as Afghanistan's de jure government, so it is technically correct that the Northern Alliance flag was the official flag of Afghanistan in the late '90s. A new Afghan flag was adopted following the defeat of the Taliban in 2002, so the flag does date the game to before that.
"DO IT, ROCKAPELLA!" Some consider that famous theme song a Bootstrapped Theme for the entire franchise (Where on Earth, Where in Time, and the 2019 series' themes notwithstanding... though even the last one has since acknowledged how iconic it is).
The "How much you gonna risk?" and "Where do you wanna go?" think music.
"The loot! The warrant!" It might be said several times in an episode before The Crook is found.
Fridge Logic: During the bumpers that bookend the show, the Chief mentions that Carmen's gang is bankrolled by the Corporation for Public Broadcasting and Viewers Like You. Sure, the Chief is just talking about the show itself, but she comes off sounding as though VILE gets its money not through theft, but from generous donations, and doesn't sound the least bit concerned.
Genius Bonus: Rockapella's flourishes during the second round often got rather creative in order to stay on the standard rhythm. An episode featuring a looted railway used "finagled funicular!" and one about kidnapped whales included "sedated cetaceans!"
One episode had Double Trouble stealing the World Trade Center. Fast forward a decade later...
Double Trouble also stole the famous replica of the HMS Bounty, which has since been lost to Hurricane Sandy.
In the second round of the episode "White Out", a contestant picks Baldy Mountain and Rockapella says, "Greg's been there!" Greg then jokes that this will be Rockapella's last year on the show. In fact, this was from the last season before World changed to Time, so it really was Rockapella's last year on the show.
Top Grunge stole the entire rhinoceros population. Now one subspecies of black rhino has gone extinct.
In "Signed, Stealed And Delivered," the Chief describes Patty as "Carmen Sandiego's twinkling teenage terrorist." Let's just say the word "terrorist" would not be used so blithely on a children's program after 9/11.
Heartwarming Moments: In "Tango Mysterioso", the special informant is Greg's own mother. Greg did not know this ahead of time, and was shocked to see her on the screen. During and after her clues, he was visibly holding back Manly Tears. He then says, "Can we please have a nice round of applause for the finest informant ever on this show?"
Lynne Thigpen made an appearance on Sesame Street playing an official for the worm version of NASA around three and a half years after Robocrook stole NASA Space Camp.
In Seasons 3 and 4, the Chief traveled from Greg's office to the Jailtime Challenge via a small screen that Greg would pull out of his TV set upon leaving and later insert into the Jailtime Challenge board. In a sense, the technology of this portable screen is eerily similar to a Nintendo Switch - twenty-three years before said console was even revealed.
The presence of Mayim Bialik in the celebrity episode, given that she would become a Jeopardy! host as an adult.
Older viewers usually only watched the show either for Rockapella's antics, or to see what logic-defying heist Carmen's goons have pulled off (and keep in mind, they're always able to make off with things they realistically shouldn't, such as buildings, monuments, an entire railroad, even abstract concepts on occasion - and one time, the Earth's core was somehow stolen without any consequences to the planet's physical integrity).
With the advent of YouTube, people will watch an episode just to see someone defeat the infamous Africa map.
Nintendo Hard: The Surprise Difficulty was in the bonus game, where the contestant carried around posts and marked off countries on a giant floor map — starting from the north side, which made the map appear upside-down to the contestant. Even if you knew all the answers, the fact that they needed exact placement (seriously, the posts didn't work if they weren't perfectly on top of the target), the actual shuttle running and keeping the things from falling over, coupled with a brutal time limit, made it extremely hard to win. Usually, one double-miss meant Carmen could safely escape.
Ironically, every season after they changed to 8 markers had more grand prizes awarded than Season 1 (even when they added bodies of water as potential locations in Season 4).
The Africa map in particular is generally believed to be the hardest of the maps, due both to its high country tally and the fact that many kids are simply not that familiar with its geography compared to the other continents. Victories on the Africa map did happen, but they were rare.
Squick: At least a few episodes had the Chief somehow grow an extra face to try to help with searching for Carmen before Greg convinces her to make the prize a trip to anywhere in the lower forty eight U.S. States (or North America depending on which season you're watching.) There was also one episode where the Chief's head POPPED OFF and the reason she called Greg into her office was to help her screw her head back on (while still being able to talk somehow...). Could also count as Nightmare Fuel if you don't know that it's all special effects and/or try to consider how that could have happened.
Tear Jerker: During The Chief's Office sketch in "The Nefarious Nobel Napper", which are typically comedic, there's one where Greg is in the office while Da Chief is late and discovers a "Dear John" Letter from a guy named Horus, who is implied to be The Chief's boyfriend. As the Chief comes in and tries to play it off, after Greg leaves The Chief retrieves a hidden portrait from her desk and begins sobbing while saying Horus' name.
That One Level: As mentioned several times on this and the main page, the Africa map in the bonus round. Its country count is unusually high and the target audience of the show tended to be the least familiar with that region of the possible maps for the round. As a result, it was infamous for having the lowest win rate of all of them, on a round already infamously brutal in its difficulty, so any wins on this map effectively made the contestant a Memetic Badass by default.
Unintentional Period Piece: During Season 1, much of the geographical information was rendered outdated due to the rapid collapse of the communist bloc in Eastern Europe that signalled the end of the Cold War. Starting in Season 2, a disclaimer was added at the end that all information presented was accurate at the time the episode was recorded, and the date said episode was recorded was even included. This is one of the reasons the series has never received a home video release, as well as basically disappearing from television after the '90s.
Some consider that famous theme song a Bootstrapped Theme for the entire franchise (Where on Earth, Where in Time, and the 2019 series' themes notwithstanding... though even the last one has since acknowledged