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5 Things Obi-Wan Kenobi Should Have Told Luke Skywalker (Instead of LIES)

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5 Things Obi-Wan Kenobi Should Have Told Luke Skywalker (Instead of LIES)

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5 Things Obi-Wan Kenobi Should Have Told Luke Skywalker (Instead of LIES)

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Published on December 19, 2018

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Calling yourself “Old Ben” is fine. Saying mean things about someone’s uncle is rude yet necessary. Pretending that you don’t remember your BBF’s old copilot droid is crappy, but saves time. Does that excuse all the outright lies that Obi-Wan Kenobi tells to Luke Skywalker? Maybe if those lies were truly essential to getting the kid to bring down the Empire. But they’re not, so most of those lies (and omissions) are pretty egregious.

Here are a few things that Obi-Wan could have said to avoid the most ridiculous ones. Because let’s face it, most of Ben’s lies are just kind of… ill-conceived.

 

1. Darth Vader and Your Dad Are the Same Guy, Sorry That Your Dad is Evil

When I’m trying to explain to people how I screwed something up, I always come up with a story—for framing purposes! Let’s say I kind of missed out on preventing a friend’s fall to evil? When I tell that story, I make sure to separate my friend into two different entities; the guy I drank brewskis with, and the fellow I trained who murdered the guy who I drank brewskis with. Two totally different bros. That sounds like a nicer story, yeah?

Okay, there are a few legitimate reasons for not immediately explaining to Luke that Vader is his dad. And telling the kid that Vader murdered a father he never knew is a good way to get him to care about bringing down the Empire. But there are so many ways that this plan could have backfired. Luke could have easily gotten fixated on vengeance. He could have said whoa, that’s kind of freaky, maybe I should sit this one out. He could have decided that he needed to know much more, and grilled Obi-Wan long after Alderaan had been reduced to space dust. Creating this whole goofy backstory about how Vader killed Luke’s dad just reads like a desperate attempt from Obi-Wan to sidestep the unfortunate fact that he is partly responsible for Anakin’s turn to the Dark Side. He’s really lucky that Luke didn’t tell his Force ghost to shove it once he learned the truth on Cloud City.

 

2. Your “Uncle” and Your Dad Only Met, Like, Once

Doesn’t it seem like one of the easiest ways to get Luke ready for a space-faring journey away from his family on Tatooine would have been to clue him in that they… weren’t really his family? Sure, neglecting that fact is kinder, but it results in Obi-Wan spinning this wild story about how Luke’s Uncle Owen didn’t “hold with your father’s ideals” and told his dad not to get involved in the Clone Wars. Which never happened because Owen Lars is Anakin’s step-brother, and the only time they met was years before Luke’s birth when the prodigal Jedi son returned to Tatooine to find his mother, and ended up returning to the family homestead with her dead body instead.

Owen and Beru Lars have been good guardians to Luke all this time, but they’re not related to him. Obi-Wan could have saved himself a lot of time by just telling the kid that he was hidden away to protect him from the Empire, and now it’s time to step out. It probably would have been a shock still, but at least you don’t have to spend several hours convincing the kid that he doesn’t have to do what his uncle taught him. It shouldn’t be a hard sell to get a teenager away from a life of moisture farming, but Luke is weirdly reasonable for an adolescent (trips to the Tosche Station not withstanding).

 

3. Here’s Some Background On the Jedi Order and the Empire

This isn’t a lie, but it is a gigantic omission that contains a lot of vital information. This is what you get for being shortsighted and short on time. Obi-Wan (and Yoda too, for that matter) give Luke practically zero background information on the war he’s entering into. It’s obvious why; they want Luke to do something very specific, wiping out the Emperor and his right hand guy. They’re not in education mode, they’re in weapons-making mode. As a result, Luke gets no rundown on the Jedi Order, their downfall, or the rise of the Empire. He gets the micro tale over the macro one — the Empire is the reason your dad is evil. Care about that part.

But the rest of that stuff? Is kind of important for the future that will come about if Luke is successful. If he doesn’t know much about the Jedi, he’s stuck putting the pieces together after the fact. Which could cause all the same problems that led to their destruction and a mega-evil Empire all over again. Case in point? From what we know about Luke post-Return of the Jedi, his whole new Jedi school kinda blows up in his face. When he fails to prevent the fall of his nephew. Does this sound familiar? I feel like I’m repeating myself. I feel like this also could have been avoided if you’d given him some Jedi books from the Jedi library. (I know, they’re gone now. But people have some holocrons of knowledge squirreled away and Yoda was old enough to have a lot of facts stored up that in green brain.)

 

4. Burying Your Feelings Deep Down is Not a Good Way to Defeat the Emperor

To be fair, this is one of those places where Obi-Wan got so good at lying, he even lied to himself. On a regular basis, in fact. It sort of makes sense, considering the fact that his best friend in the whole universe went berserk and killed practically everyone they knew, younglings included. Problem is, Obi-Wan bought into the Jedi doctrine wholesale, even in the places where it obviously came up short. Insisting that Anakin keep his emotions buried is part of what caused his fall to the Dark Side. His advice seems really even on this account—your feelings are a credit to you, but they might be of use to the Emperor, so just push them way down there—but it’s advice that also goes against all of his former training. Most of Obi-Wan’s first lessons to Luke in using the Force were about “trusting” his feelings and “stretching out” with his feelings. We’re mixing our messages here.

More importantly, trusting those feelings as he was initially instructed is how Luke actually works things out in the end. After burying his feelings until he rage-explodes, the kid finally takes a pause in the middle of thrashing his pops and realizes that he’s gone too far. He takes a deep breath, re-centers himself, and tells the Emperor that he will always be a Jedi—just like his father was. This declaration, along with some previous needling is precisely what allows Anakin Skywalker to resurface and kill the Emperor. If Luke had kept his feelings buried, he probably just would have wound up dead, and nothing would have changed. Emotion was the name of the game.

Of course, the most important lie-by-omission has a lot less to do with the Force…

 

5. That Princess is Your Sister, DO NOT Spend Time Thinking That Your Sister is Cute

Dude, we’re not in the Dune universe. Mating with your sister to keep the bloodlines pure is not a thing that we do around here. Letting this kid think that the princess in that holovid message is cute, then walking him onto one of the most dangerous weapons in the galaxy to rescue her? Ben, you know how forbidden love works. You’ve witnessed it, this is not funny, do your damn job and tell the kid that the princess is his sister. It’s like you don’t even remember that Order 66 was a thing, or that your apprentice and best pal flipped out when he thought that his secret wife was going to die.

You’ve witnessed enough of the Skywalker family to know that they’ve got some issues around their emotions, you are just setting this kid up to fail, what I’m saying is that it’s your fault that they kiss okay? THIS IS ON YOU, CRAZY OLD BEN. You didn’t even have to say sister, you could have just told Luke that Leia was his cousin! Someone he should feel weird about making googly eyes at. You could have stopped all this terrible confusion and prevented both those kids from needing serious therapy later on. You chose not to do that, Obi-Wan. You should feel bad.

Originally published in October 2017.

Emmet Asher-Perrin thinks that Obi-Wan should have stuck to what he was good at — snark and flirting with villains. You can bug her on Twitter and Tumblr, and read more of her work here and elsewhere.

About the Author

Emmet Asher-Perrin

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Emmet Asher-Perrin is the News & Entertainment Editor of Reactor. Their words can also be perused in tomes like Queers Dig Time Lords, Lost Transmissions: The Secret History of Science Fiction and Fantasy, and Uneven Futures: Strategies for Community Survival from Speculative Fiction. They cannot ride a bike or bend their wrists. You can find them on Bluesky and other social media platforms where they are mostly quiet because they'd rather talk to you face-to-face.
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stevenhalter
6 years ago

At a meta-level, none of those things were lies when Ben told them. Lucas didn’t have a clue what he was going to write next. He didn’t know that Darth was Lukes father or that Leia & Luke were siblings.

BonHed
6 years ago

For #2, Ben must have told Owen what happened, or at least enough to convey that Luke’s dad did some seriously bad things. They didn’t have to have met more than once for Owen to not like what Anakin became. And Owen was family; even a step-uncle is still family to some degree. Maybe not blood relative, but that’s still family.

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Brett
6 years ago

It’s really weird what Lucas did with Owen and Beru Lars. They later established that Anakin’s mother married Cliegg Lars, making Owen her step-son – but why not have that be a thing in Phantom Menace, so it can be set up early on that Owen and Anakin are step-brothers? They could just say that the whole family is enslaved in some way at that point in time.

As for #1 . . . that’s pretty much on Obi-Wan. I think we’re supposed to read that as a rationalization for himself – he prefers to believe that Anakin was killed by Vader, because the truth is a painful reminder. Of course, as stevenhalter pointed out, the “meta” reason is that Lucas hadn’t nailed things down yet with their backstory.

 

rowanblaze
6 years ago

I agree with Steven, most of these were not lies until Georgie decided not to watch his own movies over and mesh them into what he’d said previously about the fall of Anakin Skywalker. He didn’t decide Vader was Luke’s father until the second movie. And he didn’t decided Leia was Luke’s sister (and the “other” Yoda spoke of) until writing what became ‘Return of the Jedi.” Heck, “Darth” was clearly intended to be Vader’s first name, not some title for Sith Lords.

Lucas’ constant fiddling with the story ruined Obi-wan’s character. But George never really cared about the story anyway. He only cared about the cool visual effects he could pay others to develop show off.

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6 years ago

@1, agree that anything in Episode IV doesn’t count, because there’s tons of evidence that Lucas hadn’t made up his mind on any of that yet (and plenty more that suggests that Alec Guinness wouldn’t have wanted to learn backstory even if he had). However, #4 is the exception. Whether or not Obi-Wan’s advice about emotions and individual attachments is morally right is maybe the central issue in ethical debates rooted in Star Wars but applicable to the real world.

Going anywhere with that leads deep, deep into issues of Buddhist/Taoist derived ethics of emotion v. Christian and Aristotelian ethics of emotion. I think I don’t wanna touch that with a ten-foot pole on the Internet, even in a smart, well-behaved community.

Taberius Rex
6 years ago

I love these. I realize they’re written for fun, but it makes me think deeper about the universe and what reasons might exist for the lies.

For #1, that’s a pretty bad lie. The only explanation I can come up with is that Obi-Wan is actually ashamed of it. Definitely the part about Anakin turning to evil, but also probably that he didn’t finish him off and instead paved the way for Anakin to become a burned, tortured person. I’d believe that this is a lie he tells himself (encouraged by Yoda, no less!) to get through the day.

(Also, when did Obi-Wan become aware that Darth Vader had survived?)

He also probably hoped that Luke and Vader wouldn’t cross paths anytime soon.

For #2, we actually don’t know a lot about Luke’s understanding of his uncle’s place in the family tree. Given what we’ve seen, I could believe that Luke knows there’s no blood relation, especially since they don’t share a last name. It’s entirely possible he was given a sanitized version of events: his grandmother married Owen’s father and Anakin was never really around due to his spice navigation responsibilities. There was just no one left to take him in but Owen and Beru.

That doesn’t explain Obi-Wan’s line about Owen disapproving of Anakin, but it was probably something that came up during his exile. (And it might have been covered in one of the comics.)

#3 was absolutely deliberate, but I think Obi-Wan figured he’d have more time to go into all of that with Luke. I don’t think his curriculum plan involved “get bisected by Vader a few days later, leave Luke in the dark about the Jedi Order.” And the evils of the Empire would probably become apparent quickly.

#4 isn’t, I think, a lie. Obi-Wan genuinely believed repressing emotions was the path to being a good Jedi Knight. It worked for him, after all. And it’s not like Anakin took any time during their giant lightsaber fight over lava to mention, “Hey, if you’d let me talk about my emotions, we probably wouldn’t be here.” Maybe Obi-Wan never really understood why Anakin fell? That’s a hell of an idea.

And for #5, Obi-Wan was probably planning on introducing Luke and Leia once they got to Alderaan. “This is your long-lost sibling, now it’s time to get down to brass tacks and train you both to become Jedi.” Obi-Wan didn’t even know Leia was on the Death Star after Alderaan was destroyed. He probably could have mentioned it to Luke on Tatooine—the look in his eye indicates a serious “oh shit” moment. (And, I would argue, the moment when he realizes exactly who R2 is; otherwise, he’s pretty dismissive of droids in general, like how you probably wouldn’t recognize your college roommate’s toaster if it showed up on your doorstep)

But that would have taken, like, a whole afternoon of talking. That’s prime cutting-off-arms-in-cantinas time.

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zelna
6 years ago

The lies about Luke’s family are at least sort of justified by the fear that Luke might spill the beans to somebody else. If Vader or the Emperor catches wind of the fact that Vader’s children are alive, it’s not going to end well; Obi-Wan has spent his many years in exile protecting this secret for a reason. Luke is a moody, excitable, and largely defenseless teenager whom Obi-Wan barely knows. What if he lets something slip to a stranger in a cantina and it makes its way back to an Imperial spy? What if he gets captured and interrogated and reveals Leia’s true identity? The “Vader killed your father” thing covers most of Obi-Wan’s narrative bases (Vader bad, Empire bad, Jedi cool and awesome, also you’re a Jedi Harry!) without being identifying.

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6 years ago

A couple of questions come up to me as I read this.  

1) lets say Luke finds out Obi-Wan lied to him and then Obi’s force ghost pops up.  Can Luke *do* anything about it?  Or does Obi-Wan get to harass Luke for eternity?  (yes, I used to watch Robot Chicken too)

2) Maybe Obi-Wan didn’t tell Luke about Leia even after he became a force ghost because Obi-Wan was a) a jerk, or b) was a perv.

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6 years ago

They were truths from a certain point of view.

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Other Chris
6 years ago

Lucas is quite obviously drawing parallels between the deceptions of the Sith and the Jedi. Obi-Wan kept the truth from Luke to protect him from the emotions that would lead him to the dark side. He and Yoda planned to mold him into another passionless perfect soldier, like the Jedi of the Republic era. Their choice in NOT confronting their friend with the truth, just like the situation with Anakin and his marriage, comes both from a desire to protect the Skywalker boys and to keep them in the classic Jedi position that they know. Anakin’s failure and Luke’s triumph prove Obi and the old Jedi wrong, and prove that the next generation should embrace their emotions and accept the truth.

 

Make the changes that you’ve laid out and you strip Star Wars of (woefully underappreciated) nuance.

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Kenneth DeLozier
6 years ago

Originally  Owen Lars was going to be Ben Kenobis brother which is why they look similar   it’s even in the Return of the jedi novelization 

rowanblaze
6 years ago

@11 Oh yeah. That brings up another point about Ben’s robes in the original movie clearly being a reflection of the desert environment he lived in. Owen wore almost the exact same outfit, and Luke’s was similar. This somehow morphed into the standard dress for Jedi. A well-known Star Wars apologist (vs Star Trek) from the ’90s and early 2000s used the term “brain bug” for just this sort of feature/detail creep from one iteration of an IP to the next.

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6 years ago

@6: I really like the idea that Obi-Wan doesn’t understand Anakin’s motivations. And it works really well in canon with the fallout of his affair with Duchess Satine. (Seriously, her Clone Wars line referring to him as “the bundle of half-truths and hypocrisy that is Obi-Wan Kenobi” is my #1 favorite bit of dialogue about Obi-Wan.)

Obi-Wan was presumably raised in the Jedi Temple since very early childhood, and on top of it has a low-emotional-range temperament and no noticeable major mental health issues. He displays very little regret about having broken off a major love affair and seems to think it’s intuitively obvious that that was the only right choice. As far as we can tell, he has no memories of his birth parents. We still don’t even know his birth planet (no, it’s not Stewjon!)

In other words, he’s actually a pretty awful mentor for both Anakin and Luke, relative to their passionate temperaments and levels of trauma (even though Luke isn’t traumatized at the beginning of Episode IV, he definitely is at the end). It’s probably a good thing structurally that Alec Guinness refused to do anything but brief ghost scenes for V and VI, because putting his Obi-Wan together with Luke for any extended amount of screen time in those stories sounds like a Terrible Idea. Though I would read the heck out of any Star Wars author who is good at dialogue digging into the debates that Luke would plausibly have had with Ghost Obi-Wan after Endor.

stevenhalter
6 years ago

mutantalbinocrocodile:I would love such a debate sequence. 

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Mike Hummell
6 years ago

This article could just as easily be called “Plot holes from the Prequels”. Ben didn’t lie, George Lucas did. The prequels simply do not lineup with the original trilogy.

Ben didn’t know R2D2, he didn’t know Leia was Luke’s sister, there was no way Darth was a title instead of a name. And Lars/Beru was never related to Luke or Darth, that family was where Luke was hiding! Why would you hide him with a blood relative? It makes the whole Last Jedi arguments seem petty and stupid.

stevenhalter
6 years ago

Here’s an interesting twist. What if Obi Wan is telling the truth on the above points? The prequels are all lies, Darth is not Luke’s father and Leia is not his sister.

Yoda and Obi Wan do lie when they “admit” to Luke that Darth is his father and Leia is his sister, but these lies could have also been forced upon them.

Luke is pissed off in “The Last Jedi” as he has found all that out at some point.

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6 years ago

@14 I’m thinking Claudia Gray would knock that story out of the park. I think she writes character and moral dilemmas better than any of the other current Star Wars novelists.

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The Fan Attic
6 years ago

“Bury your feelings, Luke–they do you credit, but they could be made to serve the Emperor…” is a little out of context here. Obi-Wan mentioned this after Luke deduced that Leia was his sister. “Your insight serves you well…” was what preceded that statement. He knew that Luke’s knowledge of the second child of Skywalker would likely be leveraged if Vader or the Emperor pryed it from Luke’s mind. He advised Luke wisely to conceal this from the enemy.

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The weakest link
6 years ago

Not remembering R2 after 20 years is notna stretch.

 

Droids are little more than amazon blue.  Xbox corvana.

 

Do you remember The first microwave you evwr used?

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Jordin
6 years ago

This is a very clever piece! Love it!

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6 years ago

Ben told the truth about R2, he never owned him. R2 was Anakin’s droid, and is a common model. There is no reason he should recognise R2 anymore than you might remember your old college buddy’s vacuum cleaner from 20 years ago. Obi Wan is never shown as having any particular droid of his own, he just uses the nearest one the order assigns until it gets blowed up. Sure, that makes him Droidist, but it also pretty much puts him in with the rest of the SW galaxy.

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Keith
6 years ago

The 77 marvel comic.  Luke has a red lightsaber. As I understand george approved of the drawing and covers. So not even sure that a red saber was associated with the sith. 

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Benny
6 years ago

“Also, Luke, someday you might become a hermit, too. Make sure it’s for good reasons and not just falling back on your old whiny self who gives up too easily.”

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Dean
6 years ago

@23: “Like if you really screw up mentoring a student, badly enough that he turns to the Dark Side and kills a bunch of people.  That’s a good enough reason.”

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Benny
6 years ago

Yup, no one is quite as bad at their jobs as Jedi.

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KatherineMW
6 years ago

For the first and third points, I go with the interpretation that Obi-Wan and Yoda were trying to square the circle of molding Luke into a weapon to destroy Vader and the Emperor, without Luke falling to the Dark Side.  First Obi-Wan tells him Vader killed his father to give Luke the motivation to take him down; then Yoda trains him further in the hope that he can kill Vader without succumbing to hate.

They didn’t want him to know Vader was his father because knowing that would make Luke unwilling to kill him – and when Luke did find out and said outright that he wouldn’t kill Vader, Obi-Wan’s response was “Then the Emperor has already won.”

They’re both given up on Anakin. Luke hasn’t and doesn’t.

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Michael Dover
6 years ago

I think the reference to Vader being a whole different person is because in a sense, he did become a different person. His personality, demeanor, and everything about him changed, adopting the new life & persona of Vader. Also he might’ve felt that Luke would be Lee’s likely to want to murder Vader if he knew he was his dad.

 As for Uncle Owen, just because it doesn’t show Ben and Owen hanging out every day, doesn’t mean that they didn’t have other interactions.

 For the emotion suppression, maybe he feels that letting emotions surface clouds your judgement. If you’re emotionally wound up, you don’t think clearly or logically. Tactically speaking, I think that’s pretty effective, since the Emperor seeks to manipulate negative or especially strong emotions. Love and hatred being two the strongest.

Some of these “problems” seem like things that an uninterested girlfriend might say after being forced to watch them. Not someone who is an actual fan.

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6 years ago

@25, hard to believe the Jedi were supposed to be the guardians of the republic for thousands of years when by all appearances the order was incompetent at the highest levels.

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TheRuralRefugee
6 years ago

The writer states that this isn’t Dune ( in reference to cousins and siblings marrying/mating.  But somehow, the next episode is currently titled Star Wars Episode IX.  What next, Face Dancers and a Spacing Guild tie in😁

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zelna
6 years ago

@29, psh, obviously the title isn’t related to Dune! It just means that the movie will not be able to satisfactorily explain what a hrung is, nor why it should choose to collapse on Betelgeuse Seven.

Anyway, @13, I appreciate your analysis of Obi-Wan’s character. The way I see it, Obi-Wan is truly a Good Jedi, and that’s both his major strength and his major failing. He lives and dies by the teachings of the Order, and his understanding of people who can’t or won’t live that way is abstract, and simplistic, at best.

(Yoda, I think, understands better, but he’s so wrapped up in the concept of guiding/righting the cosmic balance of the universe that it clouds his judgment when it comes to dealing with actual people.)

Jason_UmmaMacabre
6 years ago

Side note: Paul II and Ghanima did not mate after Children of Dune. They married to secure the Imperial throne. All of the Atreides after that were the decedents of Ghanima and Farad’n Corinno, aka Harq al-Ada. 

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6 years ago

Another good essay. @1 Hit the nail on the head with the very first comment. This is why it pays for authors to map out their backstory more carefully. Otherwise, expanding your original tale turns into a big mess.

trike
6 years ago

This is why Empire Strikes Back is the worst Star Wars movie. Everything that’s wrong with the prequels has its roots in ESB. The impulsive, gee-wouldn’t-it-be-funny twist of “I am your father” upends everything. Kenobi becomes a liar while Leia is just using Luke in her power grab.

in fact, the only person who is honest with Luke is Vader. Looking at it from Luke’s point of view, why *wouldn’t* he join Vader? He’s the only one telling the truth and not using Luke.

From a story and character perspective, it would have been far better if Vader were lying about the whole paternity deal, but he’s so powerful and persuasive that he manages to get Luke to believe him. Now THAT would’ve been cool.

Another side reason ESB is terrible, aside from the horrible special effects, is Yoda. That hairy frog is an idiot. People ding Mark Hamill’s acting, but the only decent thing in ESB is his acting. The sole reason Yoda is even a thing is because Hamill commits to that part and makes you buy he’s talking to a person rather than a puppet.

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6 years ago

Ben was not in fact lying when he says Vader killed Luke’s father. He really does think of it that way. Darth Vader is NOT the boy he raised and loved. He is not the man who married Padme and begot Luke and Leia. That man is dead, devoured by the Dark Side. Ben wants Luke to love, admire and be proud of Anakin Skywalker. He believes Luke must kill Darth Vader. He doesn’t want the boy to be conflicted over either action.

Of course Ben is shown to be dead wrong but that’s how he’s thinking in A New Hope.

Anthony Pero
6 years ago

@34:

I’m afraid I have to disagree. Here’s the exact quote:

Luke: “How did my father die?”

Ben: “A young Jedi named Darth Vader, who was a pupil of mine until he turned to evil, helped the Empire hunt down and destroy the Jedi Knights. He betrayed and murdered your father.”

If Ben considers Darth Vader to be a separate person from Anakin Skywalker, then he is lying to Luke when he says Darth Vader was his pupil before he turned to evil. Because Vader didn’t exist before Anakin turned to evil, and Anakin was no longer Ben’s Padawan.

If Ben doesnt consider Vader to be a separate person then Anakin, then he is lying when he says that Vader betrayed and murdered Luke’s father.

In both cases, Ben is lying to himself about what happened. That’s what he means when he says in Return of the Jedi that many of the “truths” we cling to depend upon a “certain point of view.” It’s an intentional self-deception designed to protect us from a hard truth that we don’t want to consider. 

In Ben’s case, that’s the feeling inside of him that he failed Anakin as Master. There is no reasonable way in my mind to interpret Ben’s statement as anything other than a deception. Which is the same thing as a lie to reasonable minds.

To put it in Wheel of Time terms, there’s a reason the Aes Sedai swear “to tell no word that is untrue” on the oath rod, rather than to swear “not to lie” on the oath rod. Because deception is still a lie. Even when the person you intend to deceive is yourself.

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6 years ago

I shouldn’t have said he wasn’t lying. What I meant was ‘a certain point of view’ is how he manages to go on living and he thinks it is the truth. He decorated it to deliberately give Luke the wrong impression. I think he and Yoda did intend to tell Luke the whole story, when he was ready. IE: when they believed he’d see it their way.

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6 years ago

Especially in light of The Last Jedi, I do wonder how Luke learned about Darth Sidious, the balance of the Force, and all that. He must have found some sources at some point.

Honestly, I wish more had been focused on (such as that really awesome deleted scene where he tricks Rey into thinking there are marauders on the island) Luke unpacking a lot of that, and dealing with some of the more problematic aspects of the Jedi in the Old Republic. I like Obi-Wan a lot, and think in general he represents a good ideal of what the Jedi could have been, but even he is not perfect. The Jedi of old were still a little too detached and even Obi-Wan was shaped by some of those ideas about ‘burying’ your feelings and a complete lack of attachment. This isn’t to say I think Obi-Wan was 100% wrong, either – emotional control is vital. But that’s different than denying emotion. I would have liked to see Luke come up with a true balance – not the sterile way of the old Jedi, but not the total free for all of the Sith, either.

I totally agree that Obi-Wan never truly understood Anakin (and by some extension, Luke). I’m reading some old Clone Wars novels by Karen Miller (Legend EU) right now, and one of the things it does is flesh out the relationship between Anakin and Obi-Wan. It’s a close relationship in many ways, but there’s a constant source of tension in that Obi-Wan really has no frame of reference for understanding Anakin’s ongoing trauma about his slavery, the loss of his mother, etc, and keeps chiding him about getting ‘attached’ to the various people they come into contact with instead of taking the more pragmatic view he was groomed for. (Interestingly, this version of Obi-Wan also has an almost-affair with another Jedi that he broke off and basically views as having been the right thing to do, although it causes him some anguish which he frequently just pushes down. As the reader, you’re not supposed to see it as a good thing. These books were written very early on in the Clone Wars TV series run, but eventually were more or less discarded when the show went in its own direction).

But when it comes to dodgy mentors playing their own game, I still think Dumbledore takes the cake ;)