December 7, 2023
Star Wars | Defining Moments: Obi-Wan Kenobi

Annlyel continues her series focussing on the defining moments of the heroes and villains of the Star Wars universe.

For me, the Star Wars prequels didn’t get a lot of things of right. In fact, they barely got anything right. The one thing, however, that all us Star Wars fans can definitely agree on when it comes to the prequels is that Obi-Wan Kenobi was the highlight of that trilogy. Obi-Wan was an immediate icon after Alec Guinness portrayed the Jedi Master so flawlessly in A New Hope, earning him an Oscar nomination for his stunning and unforgettable performance. He appeared as barely more than a cameo in the next two installments in the original trilogy but his impact on the films was monumental. When it was announced that George Lucas would be creating another trilogy and people found out they were going to have a young version of the iconic Obi-Wan Kenobi I’m sure Star Wars fans were highly skeptical.

Star Wars | Defining Moments: Obi-Wan Kenobi

With the ingenious casting of Ewan McGregor, all of that worry was flushed down the drain as he perfectly portrayed a young Obi-Wan Kenobi in the trilogy. He made the movies worth watching and his scenes in the movies were ridiculously enjoyable.

So today, on this segment of The Defining Moments, I’m going to talk about Obi-Wan Kenobi’s journey throughout the seven films that he has graced, whether it’s in a major role or a tiny cameo that’s barely noticeable. Be Warned. I would like to let you know, Obi-Wan has had an extensive history so this will be a long read.

1. Sensing the Dark Side

At the beginning of The Phantom Menace, Qui-Gon and Obi-Wan infiltrate the Trade Federation. Qui-Gon senses are muted to trouble but Obi-Wan can sense something aloof in an instant, displaying his strong sense of intuition with the Force. This gift would help him many times before his life’s end.

Star Wars | Defining Moments: Obi-Wan Kenobi

2. “The boy is dangerous.”

Before Obi-Wan Kenobi took Anakin Skywalker as his padawan he, like the rest of the Jedi Council, knew that there was something very dangerous about the Force-sensitive boy. He tried to convey his concerns to his master, Qui-Gon Jinn, but the warning fell on deaf ears. He had no idea how right he would end up being.

3. Defeating Darth Maul

After watching his master defeated by the powerful Sith Lord, Darth Maul it was the first time Obi-Wan Kenobi let hate fuel him in battle. He ferociously fought Maul in a lightsaber duel that still stands the test of time but ultimately got beaten, for he couldn’t channel his anger as well as the trained Sith. In the final moments before Darth Maul was about to finish him off he managed to use the Force to propel himself upwards, Force-pulled Qui-Gon’s lightsaber to him, and slice! Darth Maul was “no more”. This was the ultimate test for him as a Jedi padawan and he passed with flying colors.

Darth Maul

4. Qui-Gon’s Death

The hardest thing for a Jedi padawan is to lose their master and Obi-Wan was one of the unfortunate padawans to have this happen. Qui-Gon’s dying wish was for him to train the young boy, Anakin Skywalker and because Obi-Wan loved him he made sure to abide by his wishes. This was a turning point for Obi-Wan as it was what set him on the path to training who would eventually become the infamous Darth Vader.

5. Becoming a Jedi Master

With the death of Qui-Gon and the “killing” of Darth Maul, Obi-Wan Kenobi was adorned as Jedi Master by Yoda. He was also given permission to take the young boy, Anakin Skywalker, as his apprentice despite the elder Jedi’s suspicions about the consequences of training an individual to become a Jedi after they have grown up beyond the years of a toddler. As Yoda chillingly says, “Your apprentice, Skywalker, will be” this is the true beginning of Obi-Wan’s destiny.

Yoda and Obi-Wan

6. Count Dooku Tells The Truth

During Obi-Wan’s capture on the desolate planet, Geonosis, he was visited by none other than Count Dooku, Qui-Gon Jinn’s former-master-turned-Sith-Lord. In their brief encounter Count Dooku actually told Obi-Wan the truth that a Sith Lord named Darth Sidious was controlling the Republic. Unfortunately, Obi-Wan believed it was too preposterous of truth to be real but he did take the information to heart, later telling Masters Yoda and Mace Windu about the possibility of the Republic being under control of a Sith Lord.

Maybe if they had reacted quicker the events that took place wouldn’t have happened. Imagine his horror when he learned that what Count Dooku had told him was one hundred percent accurate.

7. Doubting Anakin

Anakin, by this time, is his closest friend and ally but as times grow darker and the war seems to be drawing towards an end he begins to see a new side of Anakin that he hasn’t seen before. Anakin has always been one to question Obi-Wan for his decisions and sometimes his leadership but Obi-Wan had never seen him so distrustful of the Jedi Order.

After speaking with young Skywalker about the secret mission he had been given to spy on the Chancellor he starts to feel doubt about Anakin being the Chosen One. This harks back to The Phantom Menace when he felt, through the Force, a wariness towards Anakin. He knows Anakin is one peg loose from tumbling and he’s afraid of what that exactly means. He remains hopeful that Anakin won’t turn to the Dark Side but he can already sense that he will.

Star Wars | Defining Moments: Obi-Wan Kenobi

8. Wishing Anakin Farewell

Obi-Wan was sent, by the Jedi Council, on a mission to Utapau to finally defeat General Grievous. Anakin was not sent on the mission with him and so they had to part ways. Obi-Wan knew that Anakin’s faith in the Jedi was on the edge but he believed that Anakin would eventually snap out of it. This is one of the most important moments of Obi-Wan Kenobi’s story because the next time he would see Anakin would be on the lava planet of Mustafar and that scenario would be very far from pleasant.

9. Betrayal

General Grievous was dead and it seemed like the war would finally come to an end but it was only the beginning of a treacherous nightmare none of the Jedi saw coming. Obi-Wan’s closest Clone comrade, Commander Cody, after given Order 66 blasted the Jedi Master out of the sky believing he had killed Obi-Wan. Of course, Obi-Wan survived but just imagine his shock when he discovered that it wasn’t the Separatists but his own men who had tried to kill him.

At that moment he knew something was terribly wrong and the horror was just beginning.

Commander Cody (Order 66) Revenge of the Sith

10. “It Can’t Be. It Can’t Be.”

Obi-Wan Kenobi had seen the slaughtered Jedi younglings, he knew that Darth Sidious had taken over the Republic, and he knew it was through the help of a Jedi turned bad but he didn’t know who it was that would commit such an atrocious act. Or at least he didn’t want to believe the truth.

When he saw the records and was faced with the truth that his best friend, Anakin Skywalker, was the one who had performed the unthinkable acts he couldn’t believe it. Who was this other person, this man supposedly named Darth Vader, that his friend had become? What had happened in the time that he had been gone?

I can’t imagine the sorrow he felt in knowing what he had to do. It’s not only a shocking moment for Obi-Wan but was probably also one of the saddest moments of his life.

11. Telling Padme the Bad News

Obi-Wan’s mission, placed upon him by Yoda, was to find and kill Anakin and he knew the exact person that knew where Anakin was. He had a suspicion that Anakin and Padme’s relationship was beyond mere friendship but this scene practically confirmed that as she took the news of her husband’s betrayal so hard. Because he was a very good friend of Padme’s he completely understood the utter pain she was probably feeling.

This is one of the most momentous scenes in Revenge of the Sith because of his acknowledgement of her pregnancy. To find out that not only was Anakin and Padme a couple but that they were also going to have a child was probably a heartbreaking realization for Obi-Wan, considering how Anakin turned to the Dark Side. When those children would be born without a father it would be Obi-Wan who was the cause of that and that’s a hard duty to take.

Star Wars | Defining Moments: Obi-Wan Kenobi

12. The Battle

Obi-Wan didn’t want to fight Anakin but he had to in order to protect the galaxy from anymore Anakin could’ve inflicted. They duked it out but ultimately Obi-Wan won and he had to watch as his brother of all but blood was reduced to a limbless, burnt crisp. The pain, the sorrow to find out that those suspicions he had all of those years ago would come true and he would end up being the one to have to stop this monster was probably almost unbearable for him.

In his mind when he left him there screaming on the shore of Mustafar’s burning lava river he thought he had left him for dead. How wrong he would end up being.

Star Wars | Defining Moments: Obi-Wan Kenobi

13. Witnessing the Birth of Luke and Leia

Even though he failed Anakin Skywalker he was determined not to fail his children. He watched as Padme died with the belief that Anakin was not fully turned to the Dark Side and then he became the new caretaker of the destined twins. Even though so many terrible things happened he understood at the moment when the children were born that hope wasn’t lost, for the Jedi would live on through them, and he was determined to make that happen.

14. Delivering Luke to the Lars Family

This is a haunting but hopeful ending to the man named Obi-Wan Kenobi. The world has been taken under control by the notorious Empire, Anakin is no more, and Padme is dead, but with Leia and Luke he knows that hope has found a way to live on.

He then goes into hiding, changing his alias to Ben Kenobi, and must wait for the moment when the galaxy needs Obi-Wan Kenobi to return again.

owen lars and beru

15. Ben Kenobi To The Rescue

When Ben Kenobi found Luke with the droid, R2-D2, he had no idea the Force was leading him to his eventual destiny upon the built Death Star. Imagine having to watch Luke from afar as he grew up and knowing that you can’t teach him to become the Jedi you know he can be. But, as the Force would have it, this ended up happening anyway and this tiny rescue would become something much more.

16. Telling Luke of the Force

Obi-Wan knew it was time to begin showing Luke the way of the Jedi and so, at this moment, he presented Luke with a lightsaber for the first time before telling him about the Force. It was a proud moment for him seeing Anakin’s son as a fine young man. Luke was a pilot, a farmer, but more importantly, he had that adventurous spirit that Anakin once had as his own padawan and Obi-Wan knew that spirit would eventually bring hope to the galaxy.

Ben Kenobi Reveals All

17. Facing Darth Vader

The last time Obi-Wan saw Anakin he was a burnt husk of a man lying on the planet of Mustafar. He knew that Anakin had survived and had become a cyborg of sorts but when he saw him in person I’m sure he felt a hint of that early sorrow all over again. He wasn’t going to shrug away from duelling him, for he knew that it was his destiny to face Darth Vader one last time.

This was the perfect ending to his story, for he had faced all sorts of situations and passed many trials but he knew his time as a Jedi Master had come to an end and that his true journey had just begun.


20. “Go to the Dagobah System.”

Even though Obi-Wan was dead his spirit still lived on and would help propel Luke’s destiny forward. Him telling Luke to go to the Dagobah system was not only a turning point for Luke’s story but it also showed how powerful the Jedi Knight had become, for even in death he was still able to aid Luke through the power of the Force.

21. Telling Luke the Truth

Obi-Wan Kenobi had told Luke on Tatooine about his father’s death and while it wasn’t the full truth it was, as he reminded him, from a certain point of view. He didn’t want to hurt Luke and tell him the truth about Darth Vader being his father but the Force made sure of that happening whether he wanted to or not. The sad thing about this moment is seeing Obi-Wan’s bitterness towards the man he once knew as Anakin Skywalker. Luke believed there was still good in Darth Vader but Obi-Wan highly believed otherwise. The monster that was Darth Vader had consumed the man he once knew and loved and he wasn’t ever going to allow himself to be that heartbroken again.

This scene is also important because of the infamous sister reveal. It was one of the shocking surprises in the original trilogy and Obi-Wan probably wanted to alleviate the suspense.

From a Certain Point of View

22. Three Happy Ghosts

Obi-Wan Kenobi had seen a lot of pain and sorrow transpire throughout the decades but imagine the pride and happiness he felt seeing Luke save not only the galaxy but the soul of his best friend as well. Darth Vader had been restored back into the man he once knew, Anakin Skywalker. It was a beautiful conclusion to the six-movie-long storyline revolving around and Anakin and Obi-Wan Kenobi.

23. Spurring a New Hero Forward

Thirty years after the events of Return of the Jedi the galaxy is still in turmoil but a new hero’s path with the Force has arisen. During Rey’s vision in Maz Kanata’s castle in The Force Awakens Obi-Wan speaks to her twice. At one time he says her name and at another moment he tells her, “These are your first steps.”

Because Obi-Wan has become one with the Force his spirit lives eternally and it is partly because of him that Rey ended up finding Luke, his former pupil, on that island, Ach-To. Just like the Jedi mind trick he performed on Tatooine, when he spoke to Rey there wasn’t anything elaborate about the moment. He didn’t appear floating in a cloud of hazy smoke and speaking to her in epic riddles, there wasn’t a great boom of thunder rumbling through Maz’s castle, and that is the way of the Jedi. There’s nothing fancy about their presence but their silent impact on the galaxy is immense and Rian Johnson, using the legend of Luke Skywalker, was able to build on this concept.


I honestly wasn’t expecting there to be this many moments that would define Obi-Wan Kenobi but as you look at his history (and that’s outside of The Clone Wars and Rebels) you realize just how great of a Jedi he really is. And this list will only surely increase after he eventually gets his destined series on Disney+.


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Annlyel James is a prolific Staff Writer for The Future of the Force. She is passionate about Star Wars and Marvel but loves a wide variety of movie genres. Follow her on Twitter @annlyeljames where she channels the Force frequently!


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