Dark Sided: The Most Tragic Villains of Star Wars

Did you ever hear the tragedy of Darth Plagueis the Wise™? You may not have — it’s a Sith™ story, not spoken aloud in most respected circles. But you might have heard the tragedies of many other villains from a long time ago in a galaxy far, far away.

Let’s break down their fraught histories below.

Anakin Skywalker

Anakin Skywalker™ never chooses evil; evil puts its claws in him and never lets go. A sensitive and caring man, Anakin is born a slave on Tatooine™ who is eventually freed by the Jedi™. As a Padawan™ learner in Star Wars Episode II: Attack of the Clones™ he excels, but often feels out of place and unable to control emotional impulses. He still carries attachments — he loves his mother Shmi Skywalker™, his wife Padmé Amidala, and his Master Obi-Wan Kenobi despite attachments being expressly forbidden by Jedi creed.

Often his empathy and compassion benefit his missions during the Clone Wars™, though they can also blind him, since he tends to trust those who show him the smallest kindnesses. Time and time again he loses people he holds dear: Shmi is killed by Tusken Raiders, his apprentice Ahsoka Tano leaves the Jedi Order, and he has premonitions of Padmé dying in childbirth.

Birth of a Villain

Emperor Palpatine exploits both Anakin’s fear and love, inverting any positive emotions in order to manipulate and corrupt Anakin. In Star Wars: Episode III: Revenge of the Sith™, Anakin never feels his actions are villainous. He believes what he’s doing is heroic and for the good of everyone he loves, even if only he can see that path, and his entire quest for power is simply a desperate attempt to save his family from death. However, his righteous anger continues to be exploited by the Sith, turning him into the villain that we know as…

Darth Vader

Darth Vader™ is an antagonist in the original Star Wars™ trilogy, which encompasses Episode IV: A New Hope™, Episode V: The Empire Strikes Back™, and Episode VI: Return of the Jedi™. In the first film, he seems a powerful yet rather stock villain who destroys planets, tortures our heroes, and kills a beloved Jedi mentor. Yet in the second film, our perspective begins to shift in Cloud City™ when we learn that Darth Vader did not kill Anakin Skywalker. Instead, that broken man is the same one who breathes behind the mask. Vader is the father of Luke Skywalker and Leia Organa, and his villainous behavior may be the result of someone far more … insidious … hiding behind the scenes.

During Return of the Jedi, we watch Vader try to turn Luke to the dark side and Luke try to bring his father back to the light. Their intimate filial struggle is symbolized on a larger cinematic scale by the Rebel Alliance’s plight to restore peace to the galaxy by defeating the evil Empire. In fact, Vader’s final scenes directly influence the Rebel victory. Darth Sidious™ tortures Luke with his Force lightning, and at the sight of his son’s agony, Darth Vader intervenes.

Prophecy Fulfilled

Sidious fatally wounds Vader. Although weakened himself, Luke carries his father across the Death Star to save them both. At the end, Vader asks Luke to remove his mask/respirator, which will cause his death, but he wants to see his son’s face with his own eyes. It’s an incredibly moving scene, and perhaps an indication that Anakin Skywalker is still the prophesied Chosen One, as his choice to die that day and allow Luke to emerge victorious led to the fabled balance in the Force.

Trilla Sudari / Second Sister

The Second Sister™ is the main antagonist of the Star Wars Jedi: Fallen Order™ video game. She is an Inquisitor™, or a Jedi Hunter™ that works for the Empire and uses the dark side of the force to aid them in capturing and/or executing remaining Jedi or Force-sensitive children. In most instances, Inquisitors are former Jedi with more ambition or violent tendencies than were encouraged in the peaceful Order.

In Trilla Sudari’s™ case, she was among a collection of apprentices who were taken by other Inquisitors and tortured until they turned against their previous ideals. The methods to turn a Jedi are both psychological and physical, with the end goal being complete hatred of Jedi principles as well as so much anger and pain that the dark side is the only viable power source to tap into.

Breaking the Cycle

The cunning and ruthless Second Sister pursues young Jedi Cal Kestisuntil the end of the game, where she recognizes the harm done to her, the harm she’s doing, and the cycle of abuse from her captors to her treatment of her own victims. In one last redemptive act, she fights Darth Vader to give Cal more escape time. Though the Sith Lord kills her, her sacrifice saves many lives on Nur.

Reva / Third Sister

In Obi-Wan Kenobi™, the Inquisitors are brought to live action and Reva Sevander™ is introduced. Immediately, something seems different about this Jedi Hunter. She’s obviously very powerful and skilled, and her hatred for the Jedi is palpable. Yet for some reason Reva is ostracized by her fellow Inquisitors, even singled out and belittled by the Grand Inquisitor™ himself. It seems to be related to her connection to the Force.

Third Sister™, as she’s known among the Inquisitors, gets closer and closer to delivering Obi-Wan to Darth Vader. She seeks Vader’s approval and rises through the ranks, displaying a ruthless nature that even outsmarts the Grand Inquisitor. Still, this all seems a bit personal for Reva. Her reactions are volatile and fueled by dark side emotions.

Reva’s Time at the Jedi Temple

Eventually, Reva’s past comes to light. She was one of the younglings present at the Jedi Temple™ during the Great Jedi Purge™. While Order 66™ crackled over clone trooper™ comms, she watched as Anakin Skywalker slaughtered her friends and mentors in cold blood. Miraculously, she survived the attack.

Afterward, Reva was consumed with revenge against Skywalker, whom she tracked on his path to become Darth Vader. Her rage proved to be a disadvantage not only in standing up to Vader but also in accepting help from Kenobi himself. Though she ultimately decided against killing young Luke Skywalker, lest she become another Vader, Reva’s fate is still unknown.

Kylo Ren

Kylo Ren™ is introduced in Star Wars: The Force Awakens™ as one of the main villains of the Sequel Trilogy. This dark, brooding baddie is the son of Han Solo and Leia Organa, and despite his relation to the galaxy’s greatest heroes, he’s been led astray by the dark side of the Force. In The Force Awakens, Leia, Han, and Rey think that Kylo can be redeemed. During a tense scene on Starkiller Base™, our worst fears are confirmed — there’s no turning back for a patricidal maniac. Or is there?

Over the course of The Last Jedi™, more of Kylo’s story unfolds. A scared young man who was almost cut down by his own uncle, a powerful Force-wielder with a familiar inability to control strong emotions, and now a man who struggles between his desire for power and his impulses to do good, Kylo Ren is more complex and worthy of forgiveness than previously imagined.

Ren’s Retribution

His arc culminates in The Rise of Skywalker™. Time and time again Kylo is offered redemption, and time and time again he refuses. In a fateful duel, Rey stabs him, and he faces certain death until she uses her Force healing. This event makes Kylo self-reflect quite a bit. He imagines if his confrontation with Han Solo on Starkiller Base ended differently, and at the end of this scene, he casts away his red lightsaber™ to become Ben Solo™ once more. Now on the side of the heroes, Kylo races to Exegol™ to confront Palpatine and defeat him; to do so, he transfers his life force to Rey, making the ultimate sacrifice as a true tragic hero.

Asajj Ventress

As shown in Star Wars: The Clone Wars™, Asajj Ventress™ was born into a coven of Force-sensitive Nightsisters on the planet Dathomir™. Often exploited by criminals and those in the galaxy with more power, the Dathomirians have a huge population of sisters and brothers taken as slaves, and Ventress is no exception. She serves her enslaver until he is murdered by pirates, who are then defeated by a Jedi Knight named Ky Narec™. Recognizing her talents, Narec trains Ventress, though the pirates eventually seek their revenge on him and she is orphaned once more. Alone and afraid, and under the influence of Sith Lord Count Dooku™, Ventress turns to the dark side.

She is so competent and skilled as a Sith warrior that Darth Sidious orders her execution — betrayed and left for dead yet again, Ventress soldiers on, allying with various Jedi during the Clone Wars and eventually returning home to the Nightsisters. But because her life is one filled with pain, Dooku dispatches General Grievous to slaughter her new family.

Asajj, Assassin for Hire

Forced on the run once more, Ventress turns to bounty hunting, using her skills as an assassin to survive in a cruel, unjust world.

During this time she and Jedi Knight Quinlan Vos™ fall in love … except, Dooku tortures Vos to the point of turning him to the dark side. Ventress sacrifices herself to save his life and turn him back to the light, and she is honored by the Jedi Council for her heroic deeds. Her story is a reminder to the Jedi that the pan-galactic civil war is one of the greatest harms ever wrought, and that their so-called fight for peace comes with a heavy cost.

Darth Maul

Like Ventress, Darth Maul™ was born on the planet Dathomir and his history is similarly distressing. He is a Nightbrother with a strong connection to his brothers, Savage Opress™ and Feral™. This doesn’t save him from selection by Darth Sidious, however, who selects Maul as his newest Sith apprentice. A Sith Lord and strategist, with deadly combat skills, Darth Maul quickly becomes a force to be reckoned with. Indeed, his lightsaber skills are so legendary that in Star Wars Episode I: The Phantom Apprentice™ he is able to kill Jedi Master Qui-Gon Jinn, and though Maul is defeated in the aftermath, his ruthlessness and resiliency allow him to survive.

Disillusioned with the Sith’s power structure and hierarchy, Maul and Savage Opress insist they are the true Sith Lords and lead a campaign against both the dark and light sides of the Force. For this insolence, Opress is murdered and Maul escapes, later establishing himself as a crime lord and leader of Mandalore™.

Darth Maul and the Crimson Dawn

Abandoning his allegiance to the Sith, Maul establishes the Crimson Dawn crime syndicate and amasses power through the galaxy’s underworld. While these aren’t the most heroic deeds, he often allies with heroes to get what he wants, at least aiding them and not the villains.

Maul’s last appearance is in Star Wars: Rebels™. His time on the show is brief, yet his impact is unforgettable; the Dathomirian attempts to take Ezra Bridger™ as his apprentice with somewhat pure intentions, and he also unlocks a Sith Holocron, as well as discovers Ben Kenobi’s™ hiding place. The two old rivals duel, and Maul finally finds peace in the last moments of his life.

Who is your favorite tragic villain in Star Wars? Share your thoughts with other fans at side.show/geekgroup, and don’t forget to Let Your Geek Sideshow!