Almost every Dating Sim ever, usually regarding whom your character ends up with. Some of the dodgier games even have a "Harem Ending", which allows your character to end up with them all.
Prevalent in the main works of the Nasuverse; all of them are Canon, considering the nature ofThe Verse. Various scenarios in the game are generally heroine-focused and mutually exclusive, and there are Good (happy), True (medium-happy to Tear Jerker), and Normal (outright depressing) Ends, depending on whether characters act in-personality or not, and what decisions they choose. There are also Bad Ends in the dozens, premature endings to the plot which may or may not result in death. Each Bad End will be followed by a comical, No Fourth Wall sequence where advice is given (and stupid choices are admonished) by various characters, including villains. Oddly enough, Bad Ends have a tendency to expand considerably on the Canon, to the point where the whole plot can only be figured out by seeing all of them.
Tsukihime has five heroine-focused scenarios and 9 endings total: 5 True Ends, 3 Good Ends, and 1 Normal End. Bad Ends range from being completely disabled to the infamous "eaten by a shark on the ninth floor of a hotel", followed by a "Teach Me, Ciel-Sensei!" session. Completing all Endings unlocks the "Eclipse" Epilogue where the protagonist meets with an old friend/teacher...
Fate/stay night has three different scenarios which branch out depending on several choices in the beginning of the story. The first route has a single True Ending, while the latter two have multiple endings that depend on your relationship with a specific character — one route (UBW) has a Good End and a True End (both rather optimistic), while the other (HF) has a True End (positive) and a Normal End (ungodlydepressing). There are 40 numbered Bad Ends followed by a "Taiga Dojo" sequence that either gives advice to the player or admonishes you for getting a stupidly-obvious choice wrong. One dojo even criticizes the player for looking up the very specific steps needed to reach that dojo and purposely seeking it out. Each sequence gives a "stamp" which are collected to unlock extra bonus videos.
Oh, and also once you get every death stamp and every game ending, you unlock the continuation of the Fate Route ending, revealing it to be both a Good and True end (Shirou reunites with Saber in Avalon, letting them be together for eternity in what amounts to FSN's version of heaven.) Certainly a step up for the first Fate ending.
This is, however, subverted in Kagetsu Tohya. Very often they lead you to a situation that looks very much like it should be a Bad End, such as being eaten by a Jaguar in Arcueid's room (It Makes Sense in Context... wait, no it doesn't) or having your head pulled off. Yet these are actually all necessary parts of the continuing storyline. If you want to defeat your nightmare, Nanaya, you have to let him kill you a whole bunch. The next day simply starts like any other.
School Days is known for its more unique multiple endings compared to other visual novels. But when that's said, no one cares about the happy endings, this game is infamous & notorious for its bad endings in which someone will always get grotesquely killed some way or another. Otherwise, there's those orgy-crazed endings which make the main character look more of a douchebag than he already is...
The ending picked for the anime is worse than any of the bad endings, and comes directly as a result of Makoto acting like a Jerkass to pretty much everyone he was romantically involved with.
Little Busters also plays with the multiple endings. Completing certain endings can change the main route for future playthroughs: e.g., completing Rin's first miniroute has her noticeably more confident the next time around. So far not too unusual... except for the fact that this is integral to the plot: the game takes place in a world created by Kyousuke, Masato, and Kengo after a bus crash caused the entire class bar Riki and Rin to be lethally injured, and for Kyousuke the sole purpose of this world is to make them strong enough that they can handle the aftermath on their own. So he has them repeat the same semester of school over and over, starting again each time it becomes clear they still aren't strong enough, with the different timelines having ripple-like effects on future playthroughs. Only by meeting and befriending all of the girls is Riki able to gain the confidence he needs. Therefore, it's totally possible that every single route really did happen in that world and that Kyousuke just rewound time at the end because it wasn't quite enough. To continue to talk about Earn Your Happy Ending...
Both halves of the Muv-LuvVisual Novel (Extra and Unlimited) have endings for each heroine. Unlimited happens in a continuity very different from that of Extra. Alternative (the sequel game) reveals that, like CLANNAD above, each of the routes in both ExtraandUnlimited really happened (in alternate universes), and that, similar to Higurashi below, the protagonist has (due to a complicated "quantum causality" phenomenon) lived through all of the route-universes in Unlimited, and has memories of those of both Extra and Unlimited, though he is not able to recall everything except in brief flashes. Gamewise, this is implemented by Unlimitedreading the savefile ofExtraand displaying new content accordingly, andAlternativereading bothExtras and Unlimited's savefiles in turn to do the same thing.
Following Higurashi, Umineko: When They Cry has multiple self-contained "episodes" in which things happen differently, but end in disaster for the characters involved. This time, the different episodes are different "what-if" scenarios set up by a Game Master, who exists in a "Meta World" along with "other selves" of the characters on the "game board" and witches. Events from across the episodes are used by the said "Meta-characters" in debating and arguing about the identity/ies of the culprit(s) behind the killings.
It's only towards the end of the last game when the player can actually choose between two endings: the "Magic" ending or the "Trick" ending. The Trick ending is a rather cynical one, but the Magic ending is more bittersweet. Which one is canon is ultimately up to the reader's interpretation of the events of the series.
The Magic ending can then be interpreted in two different ways depending on whether or not you believe the story is a fantasy or a mystery. The fantasy side is bittersweet, where the Metaworld is real and the ending shows how Battler finally reunites with Beatrice and his family in the golden land. The mystery approach, on the other hand, is more depressing as the ending is just a metaphor for how Tohya is finally able to come to terms with his memories as Battler. The downer part is especially apparent when it's made clear that no matter what side of the fence you are standing on almost everyone who was on the island is dead and Ange has no family left even after finally meeting her brother again.
Yo-Jin-Bo has a total of eighteen possible endings, three for each bodyguard: the Good endings involve a final confrontation with the Big Bad and a Happily Ever After, usually with Sayori choosing to stay in the past to be with her chosen love interest, while the Bad endings involve Sayori being yanked back to the present, typically immediately after she and her love interest admit their feelings for one another. And then there's the "forgotten dream" ending, in which the guy simply leaves and Sayori wakes up in the present with only vague memories of the experience and a feeling that she has lost something.
This is actually mostly averted in Suika. The first chapter has one ending, the second chapter has one ending, the third has two, but only one appears to be canon. The fourth has multiple endings and a true ending when you've unlocked both of the best endings from it. This unlocks an alternate route in the second chapter focusing on Mie and Souji's Broken Ace personality.
There are seven heroines in Canvas 2, and each one has her own ending.
In Matches And Matrimony, there are seven unlockable endings in which the player character gets married to one of Jane Austen's heroes (or villains) — and two in which she remains single.
Nine Hours, Nine Persons, Nine Doors features 5-6 endings. Most of them are of the "Bad End" variety, featuring the player's untimely death. The "Safe" ending isn't really "good," but it explains certain plot points and is necessary for completion to get the True Ending. They're all canon, as the game is being controlled by a multidimensional entity with the ability to see through time, and it was exploring multiple possibilities in order to determine the best route to ensure a little girl's salvation. Which may or may not be the entity herself, or something outside of her.
The sequel has a whopping 24 endings. In order to facilitate easily exploring them, it uses a branching game pathway that allows you to go back to points where you make storyline-altering decisions and re-do them. As in the first game, they're all canon, and the 'scene select' feature is an ability of the protagonist rather than a convenience for the player.
In the Chinese PC fan made game Fullmetal Alchemist: Bluebird's Illusion, there's a choice of 4 possible endings depending on what you've done during the game and where you've been, the most famous being Edward becoming the homunculus Pride.
Kara no Shoujo has no real good ending and a lot of downer endings. There are only two or three endings that can really qualify as bittersweet... and the true ending is not really one of them.
A Profile has five endings, two each for Miku and Rizu and one for Miou, the last heroine. None of these are bad endings, and as a whole, are all rather optimistic.
Katawa Shoujo has a Good End and Bad End for each of the five girls, plus an extra neutral end for two of them (Rin and Hanako), and a Bad End you get at the end of Act 1 if you haven't managed to get one girl by the end. In this one, Hisao has a manly picnic with Kenji, gets drunk, and falls off the roof and dies. The other bad ends generally just involves the girl becoming angry/sad at Hisao and their relationship breaking apart... which, of course, makes them much more heartbreaking.
Lilly's bad ending is unique in that the game stops after a certain scene late in the route, when she says goodbye to Hisao and Hanako, instead of showing a scene you would not see otherwise. If, however, the player has made all the right decisions, the story continues until it reaches the good ending.
Frozen Essence has six paths to choose from, and each of them have both a Light End and a Dark End. The Light Ends generally have Mina being happily together with her love interest or at least being alive and reasonably happy, while the Dark Ends generally have her dying, being resealed, or being trapped in a very twisted relationship with her love interest. In addition, the Life path has three more endings: two are more like Non Standard Game Overs than anything else, but the third one happens to be the game's True End.
Winter Shard has eight endings: a Non-Standard Game Over early in the game, a "worst" ending where Frederone dethrones Krotus and rules the entire world with an iron fist, two variations of the "worst" ending where Frederone dethrones Krotus but isn't quite as ruthless as he is in the worst ending, a neutral ending where Frederone remains in Undying Loyalty to Krotus, a "better" variation of the neutral ending where Marliene joins Frederone in his Undying Loyalty, a "better" ending where Frederone and Rosetta are married, and a "true" ending that's the most conclusive but bittersweet one.
The Yarudora series, an interactive anime visual novel franchise by Sony initially released in 1998, had this trope as one of its big specialities. Each Yarudora game would sport lots of Endings, divided in 3 categories: Good (usually 3 to 5 ones), Normal (usually 3 to 5 ones too), and Bad (usually 17 to 20 ones; Yukiwari No Hana had 32). This series, and its first game, Double Cast, in particular (due not only to the interactive anime style and the numerous gruesome bad endings, but also because Double Cast's main heroine is ultimately revealed to have a YandereSplit Personality, were so revolutionary at the time, they would become a primary inspiration for the creators of School Days cited above.
Aoi Shiro has several different types of ending. Each in addition to the numerous bad ends where the protagonist Syouko dies or becomes possessed by the <<Sword>> each co-protagonist has two or three 'Normal Ends' where everyone survives but wind up parting ways and a 'Good Ending' where they are Syouko stay together or are re-united with the same pattern for the Grand Route involving all the main heroines together. There are also a handful of route independent 'Normal Ends' that cut the story short be leaving early.
Plumbers Don't Wear Ties had this. Besides the Hollywood ending, there are other endings. The Angry Video Game Nerd, aka James Rolfe, got to the final choice screen in the game, but he ended up picking, "Gimme something different," and James Rolfe demands for another game and throws it. Taco Man, on the other hand, does not choose the chase scene, and instead picks a option that lead to an ending that was never EVER selected in the Angry Video Game Nerd's review.
Phoenix Wright: Ace Attorney: Justice for All has two endings. In the good ending, Shelly de Killer breaks up his contract with Matt Engarde, releases Maya and Engarde is sent to jail. In the bad ending, the guilty-as-hell defendant is sent away scot free, an innocent woman is declared guilty of murder and Phoenix up and quits being a lawyer. "But the miracle never happen..." Only the good ending is considered canon.
Phoenix Wright: Ace Attorney - Dual Destinies has several endings, all but one are a variation of a Non-Standard Game Over, that showed just how much you screwed up. They range from Athena being sent to jail and charged with murder, Trucy vanishing with the kidnapper and is never seen again, Simon being charged with the murder and executed on the same day, and Athena and Simon both proven to be innocent while the identity of the real killer is never found.
Dra Koi has four endings: There's a good ending where you picked all the right options, a bad ending where you either failed to go on the date or made the wrong final choice but still complete the story and then there are two bad endings that skip the final fight. Either you get killed or the dragon does, based on which of the fights you refused to step in and help out.
The Romance Games produced by Voltage Inc typically have two endings: a reasonably happy "Good Ending" in which the couple have more or less gotten together but still have some obstacles to overcome, and a "Happy Ending" in which everything works out and they presumably live happily ever after. Only rarely do they include endings that could be considered less than good, although this is notably the case in Office Secrets, which replaces the "Good Ending" with a "Normal Ending" in which the player character does not get the guy.
Dramatical Murder has ten different endings: a good and bad end for each character, with a Secret Character becoming available after you finish all the other routes. Notable for the bad endings being absolutely horrible.
Sweet Pool, made by the same company, has six endings depending on how much you gave into your "instinct" or "reason". Notable for none of the endings being happy; the least depressing one has Youji sacrifice himself to save Tetsuo and even the "true end" is soul-crushingly sad.
Sacred Sand has twenty-one endings in total and while Aydin and Rhael have the majority of these endings, you can get an ending with anyone who has a character sprite in this game. This includes the man who has a wife of his own, Rhael's brother who's in a coma for most of the game, the sort-of-villainous general, the only girl in the entire BL game world, and even Rhael's father.