- Animorphs has quite a few, most prominently Tobias, after Rachel's death, and Aldrea, once her consciousness returned to a body only to find that Dak had been killed years before. Elfangor as well fits, though to a somewhat lesser extent, because of his loss of Loren.
- F. Scott Fitzgerald's The Great Gatsby: Jay Gatsby, a genius from a humble background who, after returning from WWI to find his teenage crush married to a wealthier and hunkier man, turns himself into the richest and most popular playboy-gangster around. But of course, all he ever wanted was her.
- Since Stephen King's The Dark Tower contains pretty much every other badass-related trope, it's not entirely surprising that they've got this one as well. Most of Wizard and Glass is spent exploring Roland's Heartbroken Badass past.
- King Arthur novels:
- Older Than Steam: Sir Pelleas in Le Morte Darthur. Sir Gawain promises to help him win the heart of Ettarde, who finds him weak and doesn't return his feelings. Upon meeting her, Sir Gawain forgets his vow to Pelleas and ends up falling in love with her. Some time later, Pelleas comes across the two sleeping together and he struggles with himself whether to kill them. He decides against it and goes off, heartbroken. Soon he finds love with Nimue, and Ettarde is heartbroken.
- In Idylls of the King, it's also implied that Pelleas subsequently becomes the Red Knight of the North, who ends up horribly mutilating a peasant, among other things.
- Surprisingly, Nick Chopper in The Wonderful Wizard of Oz. He's by far the best fighter in the party, and positively deadly with the axe when Baum still had death as part of Oz. Still, the whole reason he wants a heart? He wants to return to his girlfriend and be a proper husband for her. When he does find her again? It doesn't end well for Nick. One of his live-action counterparts had equally bad luck.
- In J.R. Ward's third entry in the Black Dagger Brotherhood series, Lover Awakened, Tohrment falls victim to this once he learns his most cherished wife, Weslie, and their unborn child, were viciously murdered.
- In Ed McBain's 87th Precinct novel Lady, Lady I Did It! Bert Kling is completely broken by murder of his girlfriend Claire Townsend. It turns him not only to mere Heartbroken Badass but to real Bad Cop/Incompetent Cop. Despite his recovery from this, McBain made him constantly heartbroken because of he is repeatedly kicked, cheated and betrayed by his girlfriends and wives.
- The Heroes of Olympus: Annabeth when her boyfriend Percy is kidnapped. Her few scenes show how distraught she is, knowing that even if he is still alive, his memory has probably been erased. Thankfully this only lasts for the first book, the second book reveals he's alive and still remembers her and they reunite in the third book. The same thing goes for Nico who was in love with his friend Percy who couldn't return his love.
- Vampire Hunter Aeneas in Midnight World, after losing his wife. It took him more than 2 months to recover from Heroic B.S.O.D., and 2 years to start a new romance... which caused a new heartbreak.
- A Song of Ice and Fire: Robert Baratheon. After Lyanna died, Robert gained "200 stones", became an alcoholic, and generally lost his will to live.Robert: I was never so alive as when I was winning this throne, or so dead as now that I've won it.
- Harry Potter:
- Albus Dumbledore, who many decades ago had to defeat and help imprison the love of his young life, Grindelwald. Also, Severus Snape, whose Heel–Face Turn and subsequent badassery were driven by the death of his childhood best friend, Lily. He was by no means a perfect person, but his drive to try and fight against his former friends in her memory is admirable .
- The supplementary website, Pottermore, has also revealed that Professor McGonagall is one. She abandoned her Muggle fiancé because she couldn't part with the Wizarding World; something that her mother had done before her.
- The Dresden Files: What Murphy has become in Ghost Story following Harry's death. A rare genderswapped version.
- This happens often to Harry, Susan being the cause on at least on occasion.
- Herald Vanyel in the Heralds of Valdemar series. The love of his life commits suicide shortly after the near-fatal accident that turned Vanyel into a mage. He goes on to become one of the most powerful Herald-Mages adepts ever to live, yet to a large extent lives most of his life in mourning.
- Ripred, from The Underland Chronicles is revealed to be this in the final book. His entire family drowned in an attack and he was unable to save them, which made him suicidal (for a while). In particular, the loss of his young daughter Silksharp seems to have carried over into his "tender" and protective attitude towards Gregor's sister Lizzie.
- In Catching Fire, Katniss believes that Peeta will be able to make good use of this trope in the rebellion if she dies in the Quarter Quell and he lives.
- In Mockingjay, the trope applies to Katniss herself after losing Peeta's love.
- Luke Skywalker in the later part of the Star Wars Legends series; he's hit really hard when he loses his wife to, as he ultimately discovers, his own nephew.
- In the Honorverse, Eloise Pritchart loses the love of her life, Admiral Javier Giscard, at the Battle of Lovat. This doesn't stop her from getting even more badass as the series goes on, and she's strong enough (and has enough to live for) that it doesn't destroy her, but she never stops grieving him... and never stops loving him.
Heartbroken Badass / Literature