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Obi-Wan Kenobi Changed How We Thought About Ewan McGregor

In the 1990s, the ‘Trainspotting’ actor seemed poised to be his generation’s edgiest arthouse performer. But then he shocked his fans by doing something really daring: fill Alec Guinness’ shoes

Welcome to Misleading Men, a regular feature where we look back at the actors who ruled Hollywood for one brief shining moment.

For a lot of modern actors, you’re nobody until you sign up for your first blockbuster. Sure, you can be an acclaimed performer doing incredible work in theater or independent film, but sooner or later you’ll be lured by one of the big franchises. And whenever it happens, I always feel mixed emotions. When Oscar Isaac and Adam Driver were cast in the Star Wars sequels, it was hard not to be intrigued by the possibility of seeing what they could do on that big a canvas. But at the same time, there’s also something a little disappointing about an industry mindset that suggests that the only sure sign of being successful — of having “made it” — is that you’re cast in an event movie. Ariana DeBose was incredible in West Side Story — she’s probably going to win the Oscar for it — and now she’s doing Kraven the Hunter. Ethan Hawke, the epitome of the actor’s actor who has been rightly critical of how much superhero movies dominate Hollywood, is going to be part of a Marvel TV series. People should make the career choices they want, but it’s hard not to be a little demoralized as a viewer. All those big-budget films our best actors are signing up for potentially keeps them from the more interesting, exciting movies they could be doing.

This tension is hardly new. Ever since there have been blockbusters, there have been revered thespians who will jump at one for a sizable paycheck. In Alec Guinness: The Authorized Biography, writer Piers Paul Read mentions that the Oscar-winning star of The Bridge on the River Kwai and The Lavender Hill Mob agreed to do the original Star Wars, in part, because he was promised a percentage of the movie’s profits. Guinness was among the most respected British actors of his generation, and he somewhat famously didn’t think much of George Lucas’ sci-fi saga, but for generations of filmgoers, he’ll always be known as Obi-Wan Kenobi, the wise old Jedi who serves as a kindly mentor to young Luke Skywalker. Guinness’ regal bearing made the Force sound like a spiritual, mythic power worthy of being studied by only the most honorable individuals. Star Wars might have been just a silly, escapist entertainment — turning motion pictures into rollercoaster rides — but Guinness gave the franchise gravitas. 

For more than two decades, Ewan McGregor has filled Guinness’s shoes, but whereas Guinness always seemed a bit reluctant to fully embrace Star Wars, the 50-year-old Scottish actor has been all-in. After a while, Robert Downey Jr. and Chris Evans seemed ready to walk away from the Marvel Cinematic Universe, but McGregor has never grown tired of his association with Obi-Wan Kenobi. You can understand why: Yes, no doubt being part of a huge franchise probably has its financial incentives, but unlike just about everyone else connected to the Star Wars prequels, he emerged unscathed — if anything, he might have even been elevated in the process. Those three movies were generally disappointing, filled with lifeless performances and so much useless world-building, but if there was one ray of light, it was McGregor’s performance as Kenobi. He’s really good in the trilogy, and ever since fans have hoped he’d play the character again. And now the wait is over.

In May, Disney+ will unveil Obi-Wan Kenobi, a new Star Wars series that takes place 10 years after Revenge of the Sith. Other actors might resent returning to an old role years later — especially one attached to a group of films that weren’t especially beloved — but McGregor seems to genuinely love the chance to reprise the character. And in hindsight, the Star Wars trilogy really feels like a crucial pivot in McGregor’s professional life — one in which he made the leap from indie favorite to Hollywood leading man. Those films changed how we thought about him — just as his performance changed how we thought of Kenobi.

Star Wars ran in his family, of course: His uncle, Local Hero star Denis Lawson, played Wedge in the original trilogy. And when McGregor was 16, he (with his parents’ blessing) dropped out of school to pursue acting, too. “I didn’t hate school,” he said later. “I just didn’t get it. I just remember not liking many of the teachers. They said I had attitude problems.” 

By his early 20s, he was already doing television, and in 1994, he came to the film world’s attention thanks to Shallow Grave, director Danny Boyle’s terrific debut, which cast him as a snotty journalist who, along with his roommates, discovers that their new tenant has died — and that he’s left behind a case with a lot of money inside. Hailed as an exciting Hitchockian thriller, Shallow Grave positioned McGregor as a star on the rise — a feeling cemented by his next collaboration with Boyle, Trainspotting, a nervy adaptation of Irvine Welsh’s novel about junkies running amok in Edinburgh. 

In the wake of Pulp Fiction, myriad films tried to ape that movie’s zeitgeist-fueled hipness, but Trainspotting was one of the few that felt genuinely modern, capturing the drama of drug addiction with a fashionable techno/punk soundtrack and McGregor’s hyper-intense portrayal of the doomed Mark Renton. Released by the then-prestigious arthouse company Miramax, just like Pulp Fiction had been, Trainspotting made McGregor an icon of Gen-X defiance and disillusionment. “Every now and then, you come across someone who’s a sort of spokesperson for a particular era, someone who sums up a particular feeling or mood,” Boyle said in 1998. “Well, Ewan is one of those people. He is such a contrast to the kind of naked ambition and hardness of the ‘80s. He is perfect for this time.”

McGregor worked with Boyle one more time — the underwhelming dark romantic comedy A Life Less Ordinary — and played the Iggy Pop-ish 1970s rocker Curt Wild in Todd HaynesVelvet Goldmine, further establishing his indie-cool bona fides. At the same time, he was also cultivating a reputation for being unafraid to go nude in his movies: One profile at the time was even titled “I Do Have a Very Large Penis.” (Years later, McGregor recalled the interview, where the reporter had asked him if he was nervous about being naked so often on camera. “I said, ‘I’m not worried about it, because I do have a very large penis,’” McGregor said. “I did say those words, but I didn’t mean them. They ended up as the headline in this magazine!”) 

In other words, he was a serious actor and a sexy one — a guy who didn’t mind being a little bit of a bad boy, or causing a little trouble. Contemptuous of actors who, to his mind, sold out, McGregor had nothing nice to say about Hollywood. “They’re all bastards … the studio executives, the studio people, the people who live in L.A.,” he told Vanity Fair in 1998. “I can’t remember the last time there was a really good studio picture.” 

But he was also being a bit disingenuous considering that he’d just signed up to play Obi-Wan Kenobi in Lucas’ prequel trilogy. In that same interview, McGregor admitted, “I thought about [whether to do Star Wars] for a long time. I knew it was going to be enormous when it came out, and I’ve never been in anything like that before. I wondered how it would juxtapose with the other work I was doing. Some of the actors in the original Star Wars didn’t do anything else afterwards, and I wondered, ‘Is that going to happen to me?’” Ultimately, though, like so many modern actors who get offered a Marvel franchise, he couldn’t pass it up. Or, as McGregor put it, “When someone wanders up and says, ‘Do you want to be in a new Star Wars movie?’ it would take a bigger man than me to say no.”

McGregor wasn’t the only actor considered for Kenobi. Kenneth Branagh, Joseph Fiennes and Tim Roth were also in the running. And for all his cockiness, McGregor was actually pretty nervous about auditioning. “George Lucas was very relaxed, very calm,” he said in 1997. “He didn’t make it a big deal — it probably wasn’t a big deal to him. I did three scenes with Liam Neeson. That was really scary. I was more nervous for that than I have been for a long time. Sitting there feeling really scared again. It was great.”

In 2022, we’re accustomed to actors taking over iconic roles. (Hey, look, it’s Corey Stoll as a young Uncle June in The Many Saints of Newark. Oh wow, Henry Thomas is doing a Jack Nicholson impression in the sequel to The Shining, Doctor Sleep, which also starred McGregor.) In a world of prequels and reboots, performers aren’t just taking on familiar characters but often trying to embody the actors who made those roles famous. But that was relatively novel back in the late 1990s when McGregor was cast to play Kenobi: He was placed in the unique position of being a new actor playing a memorable individual from the original trilogy in the prequels. Liam Neeson, Natalie Portman and Samuel L. Jackson’s characters were essentially blank slates. (Even Hayden Christensen, who had the burden of becoming Darth Vader, at least was provided a little bit of separation because nobody knew what Anakin Skywalker was like.) But McGregor wasn’t just taking over Obi-Wan Kenobi, he had to become Alec Guinness — more specifically, Guinness (who died in 2000) as a younger Kenobi. 

“[I’m] trying to get that down, get the voice right,” McGregor said in 1997 about the challenge of capturing Guinness’s essence. And while much of 1999’s The Phantom Menace was abysmal — audiences hated Jar-Jar Binks and hated how Lucas had envisioned the future Darth Vader as a whiny little kid — McGregor proved to be a pretty respectable Kenobi. Granted, maybe he tried a little too hard to mimic Guinness’s speech patterns, but he successfully manifested the legendary Jedi’s quiet calm — the sense that the Force flowed effortlessly through him. 

In a 2021 interview with The Hollywood Reporter, even McGregor seemed to acknowledge that he understood fans’ dislike of the prequels — in particular, how the movies valued special effects over performances, Lucas putting his actors in front of massive bluescreens that seemed to suck the charisma out of them. “After three or four months of that, it just gets really tedious — especially when the scenes are … I don’t want to be rude, but it’s not Shakespeare,” McGregor confessed. “There’s not something to dig into in the dialogue that can satisfy you when there’s no environment there. It was quite hard to do.” 

And yet, he acquitted himself better than his co-stars. If you’d never seen Portman in anything other than the prequels, you’d be convinced she was a terrible actor. Samuel L. Jackson is one of the most magnetic onscreen presences of our lifetime — the guy is a zombie in those films. As for poor Christensen, well, it’s taken nearly two decades for fans to finally come around on him. (He’ll be in Obi-Wan Kenobi alongside McGregor.) 

Indeed, a lot of reputations took a beating because of the prequels, but McGregor survived, guiding the trilogy as best he could as Kenobi. Although those films are meant to be the saga of Anakin Skywalker’s tragic transformation into Darth Vader — the original supervillain origin story — you can also view them as a cautionary tale about how the brave, noble Kenobi failed the Republic and Anakin, paving the way for the evil Empire. I would never say the prequels are misunderstood masterpieces, but considering how overmatched Christensen was as Anakin — aided and abetted, of course, by Lucas’ clunky storytelling — McGregor managed to bring poignancy to the trilogy, illustrating how a hero can let his self-confidence get the best of him. Ultimately, the prequels are Kenobi’s sad recognition that he’s not ready to teach someone else about the ways of the Force — and what the repercussions are for his hubris. It’s been memed to death, but Kenobi’s tearful “You were the chosen one” speech in Revenge of the Sith is as close to a heartbreaking moment that the prequels ever achieved. That’s all McGregor.

In the midst of those films, McGregor’s Hollywood profile only grew. He co-starred with Nicole Kidman in Moulin Rouge!, playing the quintessential hopeless romantic, and then signed up to be part of Ridley Scott’s true-life war drama Black Hawk Down. He was paired with Renée Zellweger in the cheekily retro romantic comedy Down With Love — McGregor played the Rock Hudson role — and appeared in Tim Burton’s father-son weepie Big Fish. And then a couple months after Revenge of the Sith hit theaters, he returned with The Island, which is better known as The One Michael Bay Movie Even His Fans Dislike. The movie was a rare flop for Bay, and the producers went out of their way to blame McGregor and Scarlett Johansson for the film’s commercial failure. “We know Ewan’s not a star, but he’s such a good actor,” producer Laurie MacDonald said. Added Walter Parkes, “Those are superstars of the future, those two actors, they’re not superstars of the present.” 

Ironically, Johansson proved them right — once she became part of the MCU years later, she was huge — but McGregor never really took off in the same way. Thankfully, his initial worry that he’d end up like earlier Star Wars actors whose careers faltered didn’t come to pass. Indeed, he’s worked steadily, and been very good in arthouse fare like The Ghost Writer and Beginners. But that next-big-thing swagger of his early stardom faded away, replaced by a warm likability that seemed far removed from the cretins he played in Shallow Grave and Trainspotting. As he approached 40, he seemed at peace. “I would never draw a graph of my career,” McGregor told The Guardian in 2011. “I don’t look at things that way. On the vertical axis you could have box office, or personal satisfaction, and whenever you start thinking about that you never feel on top. There were films that were never seen by anyone but they were still important. Everything is a stepping stone. I’m sure my agents would be able to tell you exactly where I am on that graph, but I’m not sure that I want to know, really! The main thing is what’s next — the future.”

What was next was a gradual shift to becoming a character actor. In the meditative Last Days in the Desert, he was a superb Jesus — it’s the most Kenobi-like sense of serenity he’s displayed since Star Wars — and had starring roles in Christopher Robin and Doctor Sleep. He reunited with Boyle for 2017’s T2 Trainspotting. He played a candlestick in the live-action Beauty and the Beast. He was Birds of Prey’s flamboyant bad guy. He earned acclaim as part of the FX series Fargo and won an Emmy for his lead role in Netflix’s Halston. “I would say I managed to have the career I started out wanting in the first place,” McGregor said last year. “I’ve been involved in some big, silly stuff; but also lots of important stuff; and some little, silly stuff; and big, important stuff. I’ve been very lucky.”

And yet, he’s never really let go of Obi-Wan Kenobi. When Disney purchased Lucasfilm in 2012, the plan was always to develop spinoff films, and from the start, a Kenobi movie seemed like a viable possibility. And in 2017, things began revving up for an Obi-Wan movie, although at that point it wasn’t clear if McGregor was going to be involved. But the truth was, he’d been talking to the producers all along, having to keep their discussions secret. 

“Wherever I went for the last 10 years, people would ask me, ‘Would you do it again?’ Once they started doing spinoffs, of course everyone was like, ‘Are you gonna do an Obi-Wan Kenobi spinoff?’ and I was talking to Lucasfilm and Disney about that, but of course I couldn’t say that I was,” he said in 2019. “So I’d have to go, ‘Well you know if they wanted to do one I’d be quite interested in doing it,’ and it started to look a bit like I was just trying to get the part.” He echoed that sentiment in his Hollywood Reporter profile, lamenting, “[I]t was pretty humiliating to think that [Disney] might be thinking about casting someone else.” Clearly, the guy really wanted to do Kenobi again. 

But when 2018’s Solo bombed, future spinoff films were shelved, opening the door for Disney+’s Star Wars series, like The Mandalorian and The Book of Boba Fett. And now comes Obi-Wan Kenobi, which is arguably the most-anticipated project McGregor has been involved in since… well, since the Star Wars prequels. It’s funny how the passage of time allows people’s opinions to soften on things they once hated — or allows younger viewers to assert their take on a much-maligned property. It’s not hard to find defenses of the prequels these days, and even Christensen — often the focus of people’s disdain for the trilogy — has been welcomed back into the fold. In fact, the very idea that the prequels permanently besmirched the good name of Star Wars feels like a thing of the past. (Let’s be honest: As good as The Last Jedi was, the generally unsatisfying recent trilogy only underscored how much the franchise has lost its luster since its late-1970s/early-1980s heyday.) 

Those lowered expectations are probably ideal for Obi-Wan Kenobi, especially after the uniformly meh reaction to The Book of Boba Fett. That said, despite my exhaustion with Star Wars spinoffs, even I felt a little shudder of excitement at seeing Ewan McGregor in that trailer.

For a lot of Star Wars fans, Obi-Wan Kenobi was the grandfather figure we never had in real life: He was a skillful warrior with a white beard and soulful eyes who believed in Luke when no one else did. In the original trilogy, when Luke needs guidance, he turns to Kenobi, who’s always there for him. (Sure, Kenobi totally lied to Luke about Darth Vader killing his father, but never mind.) But the prequels showed that even the great Obi-Wan could be fallible, and McGregor brought vulnerability to the role while celebrating what made Alec Guinness so magisterial in the part. It’s not an imitation as much as it’s a channeling, which as an actor is a greater act of love and respect than just trying to copy someone’s mannerisms. 

The Star Wars prequels are noticeably lacking in stirring moments, but the few on display are provided by McGregor, who never before or since has played such a heroic figure. In his early career, he was more comfortable essaying malcontents and troubled souls — more recently, he’s done a little bit of everything, going from sweet to sinister. Nowadays, actors feel pressured to attach themselves to a franchise, with varying degrees of success, but McGregor’s path could be seen as a precursor to the debates we have all the time today about up-and-coming talents throwing their lot in with the Marvel empire. 

It would be inaccurate to say that Obi-Wan Kenobi is McGregor’s finest hour, but few have taken on such a memorable fictional character, played by such a revered actor, and honored both men in the process. It’s the sort of “sell out” the younger, ornerier McGregor would have hopefully appreciated.