- Air Pressure, a depressing exploration into addiction, self-abuse, need, and boredom in a relationship.
- Ever17, especially Tsugumi's and Sora's paths, or worse yet, the Tsugumi/Sora bad ending.
- Higurashi: When They Cry and its Spiritual Successor Umineko: When They Cry form an interesting variation. Their main objective is not to make the players cry, but to scare them. Despite this, the games still manage to move the player emotionally. They succeeded in doing both in both series. The question arcs are supposed to confuse and scare us, but the answer arcs are straight Utsuge. Well, except for Matsuribayashi-hen. Tatarigoroshi-hen is also fueled by tears.
- Kana: Little Sister, an image source for the trope, it's premise is based on the illness of the main character's little sister and it's exploited to the fullest extend possible in the H-Game.
- Private Nurse: Come for the marketing as an H-Game, stay for the many, many moments of crying your damn eyes out. There is basically one path that leads to a triumphant ending, the rest count as Bittersweet Ending if not outright Downer Ending.
- Saya no Uta is a Cosmic Horror love story. Besides the gorn, the nature of the bishoujo, and the other delightful elements, it fits this trope perfectly.
- Yume Miru Kusuri has three paths - one for the socially isolated school idol, one for the druggie kid, and the last one for the poor girl who is bullied with tasers in a classroom while the teacher assumes she is constantly falling out of her chair and screaming for no particular reason.
- To explain just how far own the rabbit hole this game goes, then ending of the above third girl's arc culminates in the player character and the girl strangling their primary bully while sweet and soft music plays in the background. The scene progresses to the point where the bully begins convulsing and pisses herself, followed by the two characters letting go of her throat and laughing about how close they just came to actually killing her. Despite the obscenity of it all, it still manages to come off as a highly cathartic and agreeable ending after everything the MC and girl had been put though for the last 5-10 hours of play.
- Katawa Shoujo falls under this heading as the routes can be heartbreaking. Every route has at least one Downer Ending and even some of the good endings are Bittersweet Endings. Rin Tezuka's route fits this trope the most. Hanako's route isn't too far behind, either.
- Hatoful Boyfriend. Most of the endings to the otome routes range from bittersweet to out and out tearjerkers — and that's just the main game. When you've finished all of those, there's still Bad Boys Love, the second half of the story, which, well. Let's just say it's nicknamed Hurtful Boyfriend for a reason.
- The Nitro Plus boys' love game DRAMAtical Murder is a nakige. The character routes of Clear, Koujaku and especially Ren have the most positive endings. Ren's is specifically considered the True Ending since 60% of the story is revealed in it.
- Fragile Dreams: Farewell Ruins of the Moon was so depressingly sad that even the translators for the English release were brought to tears.
- The Crooked Man is pretty sad. At the beginning of the story, the main character David has a really bad life; his sick mother can't remember who he is, his fiancée has just left him, and he's moved to a squalid little apartment. David is constantly haunted by the fact that he can never achieve his dreams of being a pilot due to his colour-blindness. Over the course of the game the ghost of the previous tenant, who was severely depressed, tries to drag David down with him. A lot of the endings feature David killing himself. At the end, just after confronting the Crooked Man, David's mother finally remembers who he is, before dying. It gets better for David, fortunately.
- Eden They Were Only Two On The Planet
- Sweet Pool is another Nitro+Chiral game that is famous, or infamous rather, for having no happy ending. All six possible endings are bad endings, and they are filled with either Tear Jerker, Nightmare Fuel, or both.
- To the Moon: You play a pair of scientists who go into a dying man's memories and try to implant a memory that he has been to the moon... except he has memory problems and doesn't know why he wants to go, so you have to find out why. Throughout the game you discover many tragic events in his life, the most well-known of which is the story of his wife's death, and their promise to meet again on the moon.
- All of the games made by the extremely popular company Key/Visual Arts, with CLANNAD often being considered the pre-eminent example of Nakige in the West. There's a reason why the Laconic page for each game ends with 'bring tissues'.
And now you know all there is to know about The Crying Game.