- Big-Lipped Alligator Moment: Rockapella once performed their song "Zombie Jamboree". Awesome? Definitely. It Makes Sense in Context? Not even remotely.
- Cowboy Be Bop At His Computer: Two of the wrong answers in a Lightning Round question were Iggy Koopa and Lemmy Koopa. None of the contestants got the correct answer. Greg went on to mention that the Koopas were from the Super Mario Bros. video game. While the Koopas are indeed from the Mario series, they did not appear in the 1985 Super Mario Bros. game. An honest mistake, to be fair.
- Ear Worm: The theme song. Oh Lord, the theme song. To the point that some consider it a Bootstrapped Theme for the entire franchise.
- 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.
- Ensemble Dark Horse:
- People often remember Rockapella more than anything else on the show.
- The Chief, to the extent that she even appeared in later editions of the computer games and even the 2019 cartoon series.
- 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.
- "Funny Aneurysm" Moment: 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, since 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 is extinct.
- Hilarious in Hindsight: 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.
- 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!"
- Just Here for Godzilla: Older viewers usually only watch 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, Patty Larceny once stole an entire railroad, and one time, the Earth's core was somehow stolen without any consequences to the planet's physical integrity).
- Memetic Mutation: Saying it again isn't necessary, but you know you want to. "Do it, Rockapella!"
- Mythology Gag: The two-note, "wrong answer" buzzer from the bonus round sounds quite similar to a sound effect from the 1989 version of the Where in Time is Carmen Sandiego computer game, which plays whenever you click on something that cannot be interacted with. Whether this was intentional or merely a coincidence is unknown.
- Retroactive Recognition: Vice President Joe Biden spoke to Greg over the phone back in 1993.
- 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.
YMMV / Where in the World Is Carmen Sandiego?