- Early in the game, Erica mentions a rumor that the enigmatic bartender, Boss, wears his Sunglasses at Night to avoid a Woman Scorned. After sleeping with Catherine and finding out she's a Yandere, it cuts to Vincent wearing a similar pair of shades while on a date with Katherine, who points out they do a lackluster job of hiding his face.
- And towards the end of the game, when Boss is revealed to be Thomas Mutton and Vincent is demanding answers about the nightmares, he suddenly shouts "AND WHAT IS WITH THESE FUCKING SHADES? YOU ARE INDOORS!" and tears off his sunglasses. Mind you, he very quickly wishes he hadn't.
- When Vincent sees that all evidence of Catherine has been removed from his phone, he says something along the lines of, "It's all gone!" and Orlando takes it to mean he's out of toilet paper. The Mood Whiplash in the scene really needs to be seen to be appreciated.
- Earlier in the same scene, Vincent wonders if he's still dreaming. Orlando points out that Vincent would then be dreaming about two guys using the bathroom together.
- In Catherine's Good/True ending:Nergal, Lord of the Netherworld: You promised you'd play video games with me tonight!
- "Fucking blocks. I'm gonna climb the shit out of you!"
- During the credits in Katherine's true ending, the second picture has a series of cakes shaped like the blocks from the nightmares. But the funny part came from Vincent and Boss arguing with the latter blowing a raspberry at the former,◊ obviously designing the cake that way just to spite him.
- Some of the text reply options can be pretty snicker worthy. For example, when responding to Katherine in an early part of a game, you can say you're too tired and your brain's full of stuff. Which results in "NOT ENOUGH THINKING POWER. SHUTTING DOWN." Then shortly after that, Catherine asks if you want pictures of her. If you're going for a chaos route, one of the answers is "PIX NAO PLZ".
- Catherine's true ending. Just Catherine's true ending. Especially when her father came. (Get your mind out of the gutter.) Also, the random succubus in the post-credits scene who falls over out of sheer lust.
- Many of the confessional questions are surprisingly funny.
- One is "What are your thoughts on underpants?" and the answers are, "It can go anywhere." or "You wear it... Under your pants."
- A noteworthy one near the end is "Would you marry the perfect...robot?" One of the answers is "Is it...fully functional?" It is worth nothing that there was a point where in the answer stats for this question, the "Is it...Fully Functional?" option just barely outnumbered the "I don't do Robots option", this means that quite a few people playing Catherine would do a robot...
- One of the early questions is "Are you a pervert? Be honest now." The poll afterwards shows that the majority of people answered to say "No use in denying it."
- "This is the bathrooom ghoooooooossssttt!"
- A mixture of awesome and funny: the defeat of the Stage 3 boss (Immoral Beast). As the boss dissolves Vincent does his little victory dance and yells "Suck it!"
- When Toby finds out that Erica used to be male.Toby: I want my damn V-Card back!!
Erica: Sorry, but once that hole's been punched, there's no refund!
- The freedom/neutral endings has Vincent arguing with Boss/Mutton over having Vincent's wish granted: Vincent wants Mutton to loan him some money... so Vincent can bet on a wrestling match. To go into detail, he was actually asking for the money ($500) to bet on a wrestling match because a god somehow wasn't able to give him 50 grand initially to go on a space trip, which, in itself, is a pretty hilarious prospect. Then in the True Freedom Ending, you really need to see the dumbfounded face on Mutton when he sees Vincent won the bet.
- Boss's hammy "FIFTY THOUSAND?!".
- There's loads of Black Comedy in Catherine's bad ending; after becoming manic after getting dumped by Catherine, Vincent runs outside to find her. He gets hit by a car. He then runs about inside the bar to let everyone know he was hit by a car.
- The fact that Boss/Mutton casually reveals that he was the one behind the nightmares and realizing that, that wasn't what Vincent was asking about is in itself hilarious, his face when he realizes this and him trying to backpedal.
- His Boss Banter, which consists of hilarious lines like "Boy, stop moving!" and "Head goes BOOM!" Yes, they're cheesy, but they work.
- In the next stage, "It's a fine night for a curse!!!"
- You might expect him to have died after defeating him in the final stage, but if you got to Katherine's Good/True end, he returns in the Stray Sheep to help back Vincent's story up... albeit with a few bumps and bandages on his face.
- There's even a moment in the drink trivia that you get whenever you finish a drink in the Stray Sheep- the unfailingly calm, informative narrator has this to say after explaining what's in a Prairie Oyster cocktail. note Narrator: Who thought this up in the first place?!
- One of the drink trivia for sake. It's referring to the old words that were used for sake. Same word can also be read as Masamune. "All that history, just for a pun?"
- Midnight Venus actually has one of this when she introduces the Colosseum Mode. As she says farewell, the camera pans away from her just like every appearance she made... when she suddenly gasps in realization that this is her only appearance in the Colosseum Mode.
- The completely out of nowhere reveal that Rin is an alien. To put it to context, this is after you finish up Mutton's stage in their true route. In the other two routes, this would be the end; you'd get your ending depending on how you chose, and finish up a few loose ends. Not here; As Vincent and Rin are about to depart from the bar, Mutton suddenly panics, and then a god damn angelic portal swallows the couple up whole, where they meet a giant angel-statue thing. And then Rin calls said angel Big Brother. What follows is an absurd obsessively protective brother act that requires Vincent to complete a new set of Nightmare puzzles before Rin's brothers begrudgingly accept the relationship and the ending makes it even better; Katherine, alongside Vincent's friends, join his and Rin's wedding. While in a spaceship. And it's shown that Jonny fell for one of the aliens on board, as well!
- Also, the fact the aliens' true form are a multitude of round, pink one-eyed blob creatures and the archangel appearance is actually their suit for going out. And as Rin warns Vincent, they're still just as powerful in this form as they were in their boss fight.
- Completing a solo Babel run as Joker leads to a quick scene where Trisha teleports into the Phantom Thieves meeting in LeBlanc to tell them that what they experienced was All Just a Dream, before advising Joker to "not get carried away" after referring to him as a "heartbreaker", referencing his promises with the girls that he has kept putting off which are brought up during the Axis Mundi stage. After she disappears, the female Thieves passively-aggressively advise him to also watch his step, probably to avoid any funny business themselves.
- See that page image up there? That's Vincent's reaction to Catherine suggesting that she breast-feed him.
Funny / Catherine