Alan Cumming: The Art of Being Entirely Himself

After four decades of refusing to fit neatly into any box, Alan Cumming, one of Britain’s most fearless performers, reflects on craft, community, and why authenticity has become his greatest role.

There are actors who disappear into characters. Then there’s Alan Cumming, who somehow disappears into characters while becoming even more unmistakably Alan Cumming. It is an improbable trick: one part extraordinary craft, one part fearless honesty, one part mischievous Scottish charm.

Over the course of more than forty years, Cumming has accumulated enough careers for several exceptionally ambitious people: actor, director, producer, author, singer, activist, television host, cabaret performer, artistic director, and even a celebrated nightclub doyen. Somewhere along the way, he also became one of the rare performers equally convincing in Shakespeare, Broadway, Hollywood, independent cinema, political commentary, and a velvet tuxedo. His résumé reads less like a career ladder and more like the guest list for the world’s most fascinating dinner party, equal parts Shakespeare, stand-up comic, political firebrand, and dinner-party conspirator.

It is tempting to describe Alan Cumming as endlessly reinventing himself, but that would suggest calculation. Reinvention implies strategy, and Alan doesn’t seem especially interested in strategy; he is interested in curiosity. Following it has taken him from a small town in Scotland to Broadway, from Cabaret to The Good Wife, from independent films to reality television phenomenon, from deeply personal memoirs to leading one of Scotland’s most beloved theatres. Every chapter appears wildly different from the last, yet somehow unmistakably connected. Like all good stories, there is a thread.

A Building in Transition

When we meet in Minneapolis, Cumming has returned to celebrate the twentieth anniversary of Sweet Land, Ali Selim’s quietly extraordinary film about immigration, identity, and belonging. Twenty years after its release, its questions feel less like history than tomorrow’s headlines.

Earlier that afternoon, we photographed Alan inside 20 Washington, Minoru Yamasaki’s architectural masterpiece as it quietly prepares for its next chapter. Watching him move through the building was unexpectedly revealing. He wasn’t interested in square footage or engineering statistics. Instead, he lingered over the curves, the changing light, and the feeling of the rooms. He spoke about architecture the same way he speaks about theatre, not as something to admire from a distance, but something to inhabit.

Inside Twenty Washington with Alan Cumming 

“I was so fascinated by the building because I realized that so much of its past was going to infuse its future,” he says. “It seems such a natural architectural fit to become a hotel. That really amazed me—how a building that was absolutely not intended to be something seems so perfect to become it. I also love its grandeur and style. I love the curves! For a building that exists in that brutalist era of architecture and can sit so well amongst the other buildings of its era downtown, it has such a feminine and beautiful aesthetic. I was mesmerized.”

It is exactly the kind of observation you come to expect from Alan Cumming. Where others might see concrete and geometry, he notices emotion. He has the curious habit of noticing what most people miss: a line buried in a script, a forgotten piece of history, the emotional temperature of a room, or the peculiar optimism of an empty building patiently waiting for its next act.

It quickly becomes apparent that Cumming doesn’t simply observe the world; he interrogates it. Not aggressively, but playfully, like someone convinced there is always another story hiding just beneath the obvious one. That perspective isn’t accidental.

Alan Cumming and the Architecture of Energy

“I am all about energy. Feng shui,” he tells me. “I think of both my life and my own work in terms of throwing a party. You need to let people know what the party is going to be like, what, if anything, they have to do or contribute toward it, and above all you have to make them feel comfortable and able to lose their inhibitions.”

He smiles before extending the idea to architecture itself. “I think certain buildings can do this too… already, even in its empty state, I feel such good energy about 20 Washington and can’t wait to come back.”

That instinct has shaped every corner of his career. It explains why his performances rarely feel manufactured, why his interviews are famously unpredictable, and why conversations with him tend to wander, joyfully, from Shakespeare to Scottish politics, from architecture to immigration, from feng shui to theatre, sometimes all within the same sentence. It is also, perhaps, why audiences have followed him so faithfully for more than four decades. Not because he has all the answers, but because he has never stopped asking better questions. In an industry that often rewards performance over personality, Alan Cumming has spent forty years performing with astonishing brilliance while quietly becoming more and more himself.

History Repeating

If “Sweet Land” feels startlingly contemporary, it is because Cumming refuses to treat it as a period piece politely gathering dust on a shelf. To him, history is less a timeline than a conversation, one that has an inconvenient habit of repeating itself until someone finally pays attention.

“I think the film couldn’t be more relevant right now,” he says, his voice calm but unmistakably resolute. Seeing the film again in Minneapolis, he reflects, was both moving and unsettling. The story of Inge, a German immigrant arriving in rural Minnesota after the First World War, is one of suspicion, bureaucracy, prejudice, and perseverance. Two decades after the film premiered, viewing it no longer feels like watching a historical drama. It feels like today’s newspaper with better cinematography.

Calling America a land of immigrants is such a contentious thing to say these days, he says. “It is, of course, absolutely true, but it is sad to realize that even one hundred years ago people were refusing to believe it—or, more precisely, choosing to believe just parts of it.”

Some things, he observes with quiet disappointment, don’t change.

Cumming has never seemed particularly interested in offering audiences certainty. He is much more fascinated by contradiction, by the uncomfortable places where history, morality, and humanity converge. That curiosity has guided his career as surely as any agent or career strategy ever could, which is fortunate, because Cumming admits, with a laugh, that strategy has never really been his thing; instead, he follows instinct.

Digging Beneath the Surface

History, he believes, is filled with stories hiding in plain sight, waiting for artists willing to dig beneath the surface. “I think history is full of secrets,” he tells me. “Artists are the people who try to find those secrets and tell them, and give meaning to them.” He says this without theatrical flourish, which somehow makes it land harder. Alan Cumming doesn’t perform conviction. He simply speaks it.

He points to one of Sweet Land’s quiet revelations: the real-life couple who inspired the film never actually married. Society refused to bless their relationship, so they simply built a life together anyway. There is something wonderfully rebellious about that. Romantic, certainly, but also quietly defiant.

Watching the film again after twenty years, however, made him reconsider that rebellion through an entirely different lens. “It made me see that to some people, breaking the law is okay if they think the law is stupid and petty and unnecessary,” he reflects. “What scared me was being reminded of how the lines in the sand of acceptance and decency have shifted—and how they can be so easily justified.”

Alan Cumming: Challenging the Narrative

It is not a comfortable observation, nor is it meant to be. That, Cumming believes, is precisely the point. “Our job as writers, actors, filmmakers is to show the underbelly and the process and the ugliness as well as the beauty of life.”

There is a temptation, particularly in difficult moments, to ask artists to comfort us. Cumming has always preferred to challenge us first. Comfort, if it arrives at all, is something we earn on the other side of honesty. It is perhaps why his performances have always felt so alive. They are rarely interested in heroes or villains. They are interested in people, gloriously contradictory, occasionally infuriating, endlessly fascinating people.

The Theatre as Town Square

For all of his success in film and television, however, the place where Cumming still feels most fully himself is the theatre. It explains why he could reinvent the Emcee without imitating Joel Grey, why Eli Gold became television’s most charming political operator, and why millions who had never set foot in a theatre suddenly discovered him presiding over the gothic mischief of The Traitors.

Mention live performance and Alan’s entire demeanor seems to brighten. “What I love most about the theatre—about live performance—is the connection with other humans.” He says it with the enthusiasm of someone who genuinely believes opening night should qualify as a national holiday. Unlike film, where months or even years pass between performance and audience, theatre is immediate. Every laugh, every silence, every held breath ricochets back to the performer in real time. “It’s magical and electrifying,” he says. “There’s nothing like it.”

The Power of Connection with Alan Cumming

As we continue talking, one word surfaces again and again: connection. Not celebrity. Not fame. Certainly not algorithms. Connection: the simple, profound act of people gathering together to share an experience.

That philosophy now shapes his work as Artistic Director of Pitlochry Festival Theatre, where he speaks less like an administrator and more like an enthusiastic neighbor inviting everyone inside because the kettle is already on. “The theatre belongs to them,” he says simply.

It is such an obvious idea that it somehow feels revolutionary. In an era when so much of culture is consumed alone and through screens, Cumming’s vision is refreshingly uncomplicated: theatre should not feel exclusive. It should feel welcoming. A place where people gather not just to watch stories unfold, but to become part of one themselves.

For decades, he believes, theatres have accidentally convinced people they were entering temples rather than town squares. Cumming would much rather they felt like living rooms. “I think for so long theatre has had an elitist, rarified reputation,” he says. “I want to smash that.”

An Act of Cultural Revolution

As a working-class boy growing up in rural Scotland, he never believed culture belonged exclusively to people with the right education, postcode, or accent. “I want people to think of the theatre as their home,” he says. “Their church.” Then he pauses before adding something that reveals almost everything about his philosophy. “Of course I want them to come and see plays and musicals… but I also want them to come into the building to get out of the rain, to have a coffee, to meet their friends.”

Only Alan Cumming could make grabbing a coffee sound like an act of cultural revolution.

Yet beneath the charm lies something surprisingly profound. He is not merely talking about theatres. He is talking about loneliness. “We have lost the sense of community in our culture,” he says. “Social media and Covid have only exacerbated this problem. I think the theatre is the answer.”

Listening to him, it becomes clear that he approaches theatre much the same way he approaches acting, architecture, or even a conversation. None of them exist merely to impress. At their very best, they make people feel seen. And perhaps that has been Alan Cumming’s greatest talent all along, not simply commanding a stage, but creating spaces where other people feel invited to step into the light.

Authenticity, Not Legacy

Near the end of our conversation, I ask Alan what he hopes remains after the applause eventually fades.

It’s an unfair question, really. How do you summarize a career that has refused summary? One that stretches from Shakespeare to Cabaret, from independent cinema to Hollywood, from deeply personal memoirs to hosting one of television’s most deliciously wicked reality shows? How do you measure a life spent constantly surprising audiences, and, by his own admission, occasionally surprising himself?

Most performers, after four decades, begin talking about legacy. Alan begins talking about authenticity.

“I believe above all that authenticity is key to everything,” he says. “It means stripping away all the external, all the froth, all the fog, all the unnecessary bits of life, and getting to the very nub of who you are and what you feel.”

It sounds deceptively simple. In reality, it may be the hardest work any artist, or any human being, ever undertakes.

Looking back over his career, Cumming doesn’t credit his longevity to clever planning, careful branding, or perfectly timed career moves. If anything, he laughs at the suggestion. Earlier in our conversation, he had cheerfully described himself as “an incredibly messy and undisciplined kind of artist,” before immediately revealing the fierce discipline that has quietly underpinned every performance.

The contradiction is pure Alan. Wildly instinctive. Meticulously prepared. Fearlessly outspoken. Disarmingly kind. Entirely himself.

“My lasting success,” he says, “is due to me being myself. Showing people who I am, even if they disagree with me. I speak out, standing up for what I think is right while supporting and nurturing people.” Then comes the sentence that lingers long after the interview is over: “Doing all that truly nurtures me.”

Reinvention vs. Revelation

It is easy to mistake Alan Cumming’s career for reinvention. From the outside, it certainly looks that way: the actor who became a singer who became a writer who became an activist who became a television host who became an artistic director. The dazzling performer who can command Broadway one evening and gleefully interrogate reality television contestants the next. The man who slips between high culture and pop culture so effortlessly that the distinction begins to feel rather old-fashioned.

But perhaps there has never been any reinvention at all. Perhaps there has only ever been revelation. Each role, each stage, each book, each new adventure has peeled away another layer until what remains is simply Alan Cumming: curious, mischievous, empathetic, occasionally gloriously inappropriate, endlessly generous, and profoundly unwilling to pretend to be anyone other than himself.

That may explain why audiences have followed him so faithfully for more than forty years. Not because he is fearless. He isn’t. Not because he has all the answers. He doesn’t pretend to. But because he keeps asking better questions, questions about belonging, kindness, community, and history. Questions about who gets invited into the room, and who has been waiting outside for someone to open the door. And perhaps the biggest question of all: what does it actually mean to live authentically in a world that profits from performance?

Fourteenth Street to 20 Washington

As our conversation comes to an end, I find myself thinking back to the first time Alan and I met. We were neighbors on 14th Street in New York City, and over the years our lives have intersected in the wonderfully unpredictable way that New York allows lives to intersect.

From those first neighborly conversations on 14th Street back in 2002 to an afternoon inside 20 Washington in Minneapolis, one thing has remained remarkably constant. Alan has always been exactly who he is: endlessly curious, effortlessly witty, profoundly kind, fiercely intelligent, and completely devoted to his craft. He possesses that rare combination of brilliance and generosity that leaves everyone around him feeling just a little more inspired than they were before.

It is easy to celebrate Alan Cumming for the performances, the awards, the books, and the extraordinary breadth of a career that has continually defied expectation. What has stayed with me most, however, is something much quieter: the consistency of his humanity. The same warmth, the same generosity, the same mischievous sense of humor, the same insatiable curiosity. The same unmistakable love: for people, for storytelling, for community, and for the endlessly fascinating process of understanding the world a little better.

Perhaps that is why his work continues to resonate so deeply. The characters may change. The stages may change. The cities may change. But the person at the center of it all never really has.

In a world constantly asking us to become something else, Alan Cumming has spent four decades reminding us of something far more difficult.

To become ourselves.

---

Creative Team:

Creative Director & Producer: Patrick Duffy @mrpatrickduffy Photographer: Victor Medina @victorrmedinac
Stylist: Kenny Washington @kennylgstylist Wardrobe: @blacknvni + @mrpatrickduffy
Hair/Makeup: Summer Rose @tentaclehaus Photo Assistant: Ella Cochrane @ellasophiafashion
Videography & Behind the Scenes: Hannah Swenson @whereshewore Cover Art Direction: @miamacfarlane
Location: 20 Washington – @20washingtonmpls

Production Special thanks:
Chad Tepley (@firesidechad) and CDT Realty Corp (@cdtrealtycorp) for opening the doors to one of Minneapolis’ greatest architectural landmarks. @alooshazooz for your generosity and support. @ronblond + @hewinghotel for your generous support.