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- A scene from Mark Latus' "Thy Kingdom Come" story, from the Sailor Moon Expanded community, has this. In the story, a portal is opened between the normal SM universe and a much Darker and Edgier Bad Future where The Bad Guys Win. The changes hinge on Calcite, who in the normal 'verse is an Aloof Big Brother who is a human-formed youma who tries to protect his family and friends from discovery, as they suffer from a genetic defect which makes them Renegades, and therefore not Always Chaotic Evil and thus open to destruction. But in the alternate dimension, Calcite takes this one step further, using his and his friends' abilities in a marvelous plan to imprison Metallia within himself. But to keep her contained, he has to calm her with negative emotional resonance, which leads him to commit greater and greater atrocities. And Now You Know.
- His true Moral Event Horizon comes when he reveals what he's done to the sailor senshi of his universe. Most were killed normally as they traveled to the north pole to confront Queen Beryl. But after Calcite subsumed Metallia, he then killed Endymion and Usagi, followed immediately by Beryl. The Outer Senshi tried to counterattack soon after, but were no match for him. Only Pluto escaped, having the ability to cast her soul into the future, rather than waiting to be reincarnated. Normally, the senshi's souls are born again and reincarnated in infants. Using a device invented by his Mad Scientist cousin, he tracks down the pregnant mothers of the reincarnated fetuses and brings them to his fortress, giving them the best medical care possible until the girls were born. Once that was done, he placed the infants into stasis chambers, which would allow aging only over the course of many decades. The plan was that when they reached adolescence, they would be released and, as teenagers with the minds of infants, be "mercifully" killed off. Only to have the whole cycle repeat itself.
- Trinity's death scene in The Matrix Revolutions managed the amazing feat of making the audience ready to scream 'JUST SHUT UP AND DIE ALREADY!' in less than six minutes. Even if it felt like six hours.
- In Reservoir Dogs, Mr. Orange gets shot early on and spends the rest of his screen time (barring flashbacks) dying in agony until he's finally shot again near the end.
- Hoster Tully from A Song of Ice and Fire lasted more than two books before succumbing - and he spent all of his appearances delirious from painkillers. In a possible acknowledgment of this, by the time he died his daughter had become inured enough to death that she barely reacted either.
- Dido in Virgil's Aeneid, making this one Older Than Feudalism.
- Stones from the River does it with both the main character's father and her dog, in an apparent attempt at Death by Newbery Medal.
Live Action TV
- Dr. Auschlander from St. Elsewhere was diagnosed with terminal cancer in the pilot episode, and residents bet on when he was going to croak. He survived 6 seasons of crises, chemotherapy, accidents, the deaths of several major characters, before dying in the final episode. (or did he...?)
- Mark Greene's death on ER.
- ...Which was preceded in pathos by Bobby Simone's death on NYPD Blue.
- Laura Roslin on Battlestar Galactica. Twice. Notable in that although her illness only becomes majorly visible on those two occasions her very first scene had her being informed she had cancer and she spent the entire run of the show dying in varying degrees. Though on that show it is likely everybody felt they were going through this trope.
- The first season of Black Adder has a Shout-Out to The Importance of Being Earnest (see below) when it mentions a character who has been on his deathbed for so long that everyone is thoroughly sick of it and want him to either recover or die, but "it's this shilly-shallying that's so undignified". That said, given that the man in question is an extremely wealthy noble, both potential claimants to his property would much rather he died asap... provided his will says the right thing, of course.
- For Better or for Worse has made Grandpa Jim progressively sicker and sicker with strokes and heart attacks, and done several "fakeouts" of his death. And has him have yet another heart attack at the end of the strip, on the day of Liz's wedding. Yet he never actually dies until the age of 89- somehow surviving two more years (he was born in 1921) after the end of the strip!
- Funky Winkerbean has Lisa who spent months slowly dying of a cancer that had returned. Every so often, there was a Hope Spot where it looks like she'd recover, but eventually she died and the creator initiated a Time Skip to the future.
- Gasoline Alley has Walt who, in order to keep up with the strip's real-time aging, has hung around to be over 110 years old, and ever more decrepit each year.
- Parodied (like everything else) in The Importance of Being Earnest. Quoth Lady Bracknell about Algernon's "sick friend" Bunbury (who Algernon made-up as an excuse to avoid unwanted social engagements, and has been using as an excuse for years) "I think it is high time that Mr. Bunbury made up his mind whether he is going to live or to die. This shilly-shallying with the question is absurd."
- Solid Snake in Metal Gear Solid 4 might qualify for this; he starts off already rapidly aging and coughing, proceeds to get the shit kicked out of him at the end of every mission, gets fried, shot, blown up, beaten, injected repeatedly for self-medication, and doesn't quit smoking. It's admirable how much punishment he can take, but Hideo Kojima is definitely punishing Snake in as many ways as humanly possible.
- Parodied in Bruno the Bandit with 'Uncle Lucius'. He's been 'dying' in one of the Bunkleyutz's back rooms for over thirty years! No one can bear to kick him out, even though he's not actually related to them - "I thought that he was your Uncle Lucius!"
- Hospitals occasionally have to deal with these sorts of people in the real world- continually sick with some unknown illness which will almost certainly kill them (or believing themselves to be so). The term used for such unfortunate figures is GOMER- Get Out of My Emergency Room.
- And even outside of hospitals, some people hold on surprisingly long before succumbing, whether to extreme old age, terminal illness, or injuries that are ultimately mortal but not quite severe enough to be quick about it.