- Complete Monster: The Ripper, who, depending on the playthrough, can be Detective Vince Magnotta, Dr. Claire Burton, or hacker Joey Falconetti, is a Serial Killer who feels inspired by the original Jack the Ripper. The Ripper uses the computer technology of 2047 to murder many people and make the murders untraceable and as graphic as possible, using a form of bioengineering to raise the victim's internal pressure to the point that their organs explode. When Catherine Powell tracks The Ripper down, The Ripper sends her into a coma.
- Dull Surprise: Dr. Burton is not particularly emotive, this is even more apparent when in a scene with Falconetti or Magnotta.
- Fridge Logic: Hamilton Wofford's cyberspace-doppleganger is called an Artificial Intelligence, yet it fails to recognise that Quinlan isn't his brother Covington. Particularly baffling, as Quinlan even says he's not.
- Ham and Cheese: Christopher Walken's performance, which can best be described as him making an hours long bad impression of himself.
- Hilarious in Hindsight
- Just Here for Godzilla: Magnotta is the reason why some people even know this game exist.
- Memetic Mutation: "Dis gai...is un-FUCKING-believable!"
Vigo: Ah, please have a seat. Now let me tell you how you fucked me...and how I'm going to fuck you.
- The game's script never misses a chance to punctuate a sentence with curses even when it renders dialogue incredibly unnatural. With special mention to Vigo's (John Rhys-Davies) introduction:
- Burton, Falconetti and Magnotta's old Webrunner photos. Especially Magnotta's, who looks like a emo.
- The surly bartender at the Cafe Du Champ, especially in one scene where he hardly even tries pouring beer into a glass.
- Narm Charm:
- Christopher Walken's aforementioned performance coupled with some of his lines:Magnotta: You're lucky I'm in a good mood today Quinlan...otherwise you'd find out what it's like...to be a human shiskebab...rotating...in one of our fine penal institutions.
- Not to mention the incredibly awkward gesture hes making while saying "Ooh, please dont" when Quinlan threatens to mention Magnotta falsely accusing Falconetti in The Herald.
- Spoony even manages to highlight an actually well-acted scene here from 11:00-11:37.
- Christopher Walken's aforementioned performance coupled with some of his lines:
- One-Scene Wonder: John Rhys-Davies shows that in one scene he can out-perform anyone else in the game, playing a Faux Affably Evil mobster who has vital information but holds Quinlan over a barrel by threatening to expose a falsified story his editor made some years ago.
- And yet he's also inexplicably drowned out by the soundtrack for most of the conversation, something that isn't really a problem anywhere else in the game.
- And he also inexplicably has a fondness for using the f-word in a very...uncomfortable connotation.
- AND... thanks to some rather oddly-designed artwork, at times it can seem as though his legs have disappeared from underneath the table. Also, his recently-thrown teacup reappears on his table. Seen here at 3:54.
- Retroactive Recognition: Paul Giamatti appears as a doctor, about 2 years before his big break in films like The Truman Show and Saving Private Ryan. Nowadays, he just naturally fits with the rest of the All-Star Cast, but when the game was made he was a relative unknown.
- So Bad, It's Good: The game's story, puzzles, cutscenes, and voice acting are really silly, but the Hollywood actors and Don't Fear the Reaper as the theme song even it out.
- That One Puzzle: For a time, there was a screenshot◊ from Ripper that was universally used as the example of a "ridiculously hard" puzzle. Specifically, you're given a motherboard with a bunch of microchips with arcane instructions and serial numbers on them and expected to put them all in the right places. The real kicker is this is just the most visually intimidating puzzle; there are puzzles that are even harder.
- WTH, Casting Agency?: Jimmie "Dy-no-mite!" Walker as a hacker.
YMMV / Ripper