The Unluckiest Characters in Fiction (and Why They Deserve It)

In the world of fiction, some characters seem cursed by fate itself. They suffer one misfortune after another, often dragging themselves (and sometimes others) through an endless gauntlet of pain, heartbreak, and existential crises. But while we may feel sympathy for their suffering, not all of these unlucky characters are exactly innocent. In fact, some of them seem to have brought their misery upon themselves through poor choices, arrogance, or outright hubris. Let’s take a closer look at some of the most unfortunate characters in fiction — and why they probably had it coming.

1. Hamlet (from Hamlet by William Shakespeare)

Why He's Unlucky:

Hamlet’s life is essentially a Shakespearean fever dream of betrayal, madness, and death. His father is murdered by his uncle, who then marries his mother. Hamlet himself is haunted by the ghost of his father, torn between avenging the murder and spiraling into existential dread. By the end of the play, Hamlet’s entire family is dead, including himself, and Denmark is left in political shambles.

Why He Deserves It:

Hamlet’s tragic flaw is indecision. Despite being handed fairly concrete evidence of his uncle’s guilt, he spends the entire play overthinking and staging elaborate mind games instead of taking action. Had he acted sooner — or not at all — he might have avoided the complete collapse of his life (and everyone else's). When you spend more time brooding and soliloquizing than actually fixing the problem, bad things are bound to happen.

2. Jay Gatsby (from The Great Gatsby by F. Scott Fitzgerald)

Why He's Unlucky:

Gatsby dies for a crime he didn’t commit, abandoned by the very people he built his life around. Despite his lavish parties and immense wealth, Gatsby is lonely and heartbroken, pining for Daisy Buchanan, who ultimately lets him take the fall for her own recklessness.

Why He Deserves It:

Gatsby's downfall stems from his obsession with recreating the past. His fixation on Daisy — a shallow, manipulative woman — blinds him to reality. He builds his entire identity on the illusion that he can win her back, even after it’s clear that she’s not worthy of his devotion. Gatsby ignored every red flag, and the universe decided to cash in on that naivety.

3. Tess Durbeyfield (from Tess of the D'Urbervilles by Thomas Hardy)

Why She's Unlucky:

Tess is seduced (or outright assaulted) by Alec D’Urberville, leading to a life of shame, poverty, and tragedy. When she finally finds love with Angel Clare, he abandons her upon learning about her past. By the end, Tess is arrested and executed for murdering Alec after he manipulates her once again.

Why She Deserves It:

Okay, Tess probably doesn’t fully deserve her misfortune — Hardy was clearly leaning into the whole "suffering maiden" trope — but Tess repeatedly places her trust in men who have already proven themselves unworthy. Alec is a predator, and Angel is judgmental and unforgiving. While society’s double standards play a major role in Tess’s downfall, her pattern of trusting the wrong people seals her fate.

4. Victor Frankenstein (from Frankenstein by Mary Shelley)

Why He's Unlucky:

Victor’s life falls apart after he creates life in the form of the Creature, who becomes a walking symbol of his failures. The Creature kills Victor’s younger brother, best friend, and wife, leaving Victor emotionally shattered and seeking revenge until he dies in the Arctic.

Why He Deserves It:

Victor's misfortune is pure hubris. He plays God without considering the consequences, then abandons his creation out of fear and disgust. Instead of taking responsibility and helping the Creature integrate into society, he leaves it to suffer — which directly leads to the creature’s violent acts. Victor essentially triggers his own downfall through cowardice and moral failure.

5. Anakin Skywalker (from Star Wars Prequel Trilogy)

Why He's Unlucky:

Anakin is manipulated by Emperor Palpatine, loses the love of his life, and ultimately becomes Darth Vader — one of the most tragic figures in cinematic history. After years of torment and regret, he finally redeems himself by sacrificing his life to save his son.

Why He Deserves It:

Anakin's downfall stems from his fear of loss and his overwhelming need for control. Instead of trusting those who cared for him, he lets his paranoia and anger drive him into the arms of the dark side. Anakin made the choice to slaughter younglings and betray his friends, and the universe handed him exactly the kind of fate that tends to follow mass murderers.

6. Willy Loman (from Death of a Salesman by Arthur Miller)

Why He's Unlucky:

Willy spends his entire life chasing the American Dream, only to realize too late that he’s been sold a fantasy. His career is in shambles, his family is fractured, and his death is framed as a tragic inevitability.

Why He Deserves It:

Willy's blind faith in the capitalist ideal — that success and wealth are the markers of a meaningful life — leads him to neglect emotional fulfillment and honesty with his family. He raises his sons to believe in empty charm over hard work and moral integrity, setting them up for failure. His misfortune isn’t just fate; it’s a product of his misguided values.

7. Ned Stark (from Game of Thrones by George R.R. Martin)

Why He's Unlucky:

Ned Stark is one of the most honorable men in Westeros — and it gets him killed. His decision to reveal the truth about Joffrey’s parentage leads directly to his execution, sparking the War of the Five Kings.

Why He Deserves It:

Ned’s tragic flaw is his rigid sense of honor in a world where honor is a death sentence. He trusted people who had already proven themselves deceitful (Littlefinger, anyone?) and mistakenly assumed that justice and truth would prevail. In Westeros, that’s basically asking for a death wish.

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The unluckiest characters in fiction aren’t just victims of fate — they’re often the architects of their own misfortune. Hamlet’s indecision, Victor Frankenstein’s arrogance, and Anakin Skywalker’s thirst for control all lead to their respective downfalls. Tragedy, in many cases, isn’t just about bad luck — it’s about poor choices, misplaced trust, and the consequences of trying to defy human nature. And maybe that’s why their stories resonate so deeply — because deep down, we know they could have chosen differently.