Alan Cumming, Maverick Golden Boy

ALAN CUMMING BY Jamie Hopper

This interview was originally published for WUSSY Vol. 13 — order a copy!

It’s well past midnight at the Clermont Lounge in Atlanta, and Alan Cumming has managed to be the first among us to land a crumpled dollar bill in a stripper’s underwear. The dancer winks at him as she plucks out the bill and snaps her panties back into place; the rest of the bar cheers—most with no idea who he is--and Cumming sits back on his stool, smiling serenely behind a pair of trim red glasses. 

It feels, as a general rule, that the best shot in the group at the strip club shouldn’t also be one of the most wildly talented performers alive today. But when it comes to Alan Cumming’s singular, almost defiantly original career, the general rules have never really applied. 

Born and raised in Scotland, Cumming shot onto the American scene in 1997 with the instant classic Romy and Michele’s High School Reunion, where he played Sandy Frink, the archetypal nerd-who-gets-a-glow-up. After that, Cumming was everywhere, madcapping his way through so many hit films that he more or less shaped the cultural landscape for two generations of American youth. From Spy Kids—where he played a villainous techno-wizard in purple tails named Fegan Floop—to Josie & The Pussycats—unctuous sidekick to Parker Posey’s would-be world dominatrix—and the movie-musical Reefer Madness—President FDR, among other roles, in a chummy mid-Atlantic accent that sounds like he’s about to burst into a fit of giggles at any moment—Cumming was the rare come-from-away performer who could perfectly parrot our bizarre American proclivities back to us. “We didn’t really do things like prom in Scotland,” he told me during the talkback at a sold-out screening of Romy and Michele. “All of that American teenage culture was new to me.” 

But the impish, larger-than-life Cumming who won over American Millennials and Gen Z’ers in the early aughts is only a slice of the kaleidoscopic performer, whose career has flourished consistently over the last forty years. After studying at the Royal Scottish Academy of Music and Drama, he launched into television in the UK, later moving into film—notably, as Mr. Elton in Emma with Gwyneth Paltrow in 1996—and live theater, including a touring production of Hamlet, opposite his then-wife Hilary Lyon, who played Ophelia. In 1993, Sam Mendes cast him as the Master of Ceremonies in a new production of the musical Cabaret, which opened in the West End but eventually brought Cumming to the U.S. Over-the-top, queer coded, and triple-threat-level demanding, it was the kind of role Cumming seemed born to play, but rather than pigeon-hole him as a perennially fey character actor, he just kept finding his way to work that challenged and delighted him. 

Since then, he’s played a buttoned-up campaign manager in The Good Wife, written and produced a movie about divorce with his friend Jennifer Jason Leigh, and gallivanted through the musical parody Schmigadoon as a Sweeney Todd-esque butcher. He’s written three memoirs, a children’s book series, and several solo cabaret shows, and owns a live performance venue, Club Cumming, in the East Village. In 2010, he appeared on the ancestry-tracing show Who Do You Think You Are, where he learned that his abusive father, who had doubted his paternity, was in fact Cumming’s biological parent; one überfan told me it was her favorite of all the work he’s done. And if for some wild reason you made it the 2020s without ever hearing about Alan Cumming, you likely know him now thanks to the viral reality game show The Traitors, where he hosts a clutch of conspiratorial contestants plotting each other’s downfall in a Scottish castle, draped in a dazzling array of tartans and kilts. (Cumming won the Emmy for Outstanding Reality Show Host for the series, ending RuPaul's eight-year winning streak; the series also won Emmys for Outstanding Reality Program and Outstanding Reality Program Cast.)

“I’ve always been a sort of maverick in both the parts I’ve played and the eclecticism of the things I’ve done,” Cumming told me over Zoom a few weeks after we met. “Of course, when I was younger, I felt more pressure to be a certain type. But it wasn’t even so much that people were saying be a type--it’s just that they didn’t quite know what to make of me.” He laughed and shrugged. “So I’ve always just done what I wanted.” 

Like others for whom the general rules do not apply, there’s a feeling of undeniability to Alan Cumming, a sense that he was always going to be who he’s proven to be. “He’s just one of those once-in-a-generation x-factor performers,” said Catherine Cohen, a comedian who performs regularly at Club Cumming and has become close with him. “He’s so magnetic, and when people want to be around you like that, it creates a sort of magic.”

You can see that magic in the earliest recordings of him, fresh out of drama school in the 1980s, riffing onstage at Edinburgh Fringe Festival with his friend Forbes Masson in their show Victor and Barry. Barely in his twenties, Cumming is nevertheless instantly recognizable, with that telltale, irreverent bravado, his grin showing off impish dimples and his luxurious hair oiled into a curl over his forehead. As a young actor, he has Hugh Grant’s casual charm and the congenital comedic timing of Eric Idle. That duality unlocked an unusual range of opportunities, which, despite Cumming’s lack of obvious type, unspooled almost immediately. “Looking back on it now, I was a bit of a golden boy,” he said, with a hint of sheepish smile. “It all just sort of happened.” 

It didn’t all start out that way. Cumming has been forthright about his traumatic childhood at the hands of a violently abusive father. The family lived on the grounds of Panmure Estate, a 17th century country home on the east coast of Scotland built for the Second Earl of Panmure, though the grand house itself had been demolished by the time the Cummings lived there; Alex Cumming, Alan’s father, was the head forester for the sprawling woods that surrounded the estate. Cruel to both Alan and his older brother Tom, Alex Cumming held a particular antipathy towards his younger son, who he was convinced was the product of an illicit affair Cumming’s mother Mary had conducted while on holiday.  Whether it was this belief itself or just young Alan’s inherently binary-resistant characteristics, Alex Cumming tormented his son, who lived in terror of the unpredictable attacks. 

“People didn’t quite know what to make of me, so I’ve always just done what I wanted.”

“I could tell by the clack of his boots, I could tell by the way he opened the door,” Cumming told the BBC radio host Lauren Laverne. “Often it would be to do with my appearance or my hair.”

From his earliest years, Cumming’s imagination became his refuge. “I used to just wander around in the woods, creating little stories and characters,” he told me. “My connection to acting was much more about making up stories.” Once he started performing in school plays, he found he had a knack for it: “It was honestly the first thing I was any good at—and I just sort of stuck to it.” 

His double act with Masson, Victor & Barry, which they developed while still in drama school, became a runaway sensation across Scotland, and within a few years they were hosting TV shows and starring in the BBC comedy The High Life. By the time his Cabaret performance on the West End earned him an Olivier Award nomination for best actor in a musical in 1993, Cumming was a well-known performer across the UK. 

Even so, he was stunned when David Mirkin cast him in Romy and Michele’s High School Reunion. “I still have no idea why they chose me!” he said. “It was my first time playing an American, and I truly knew nothing about America.” During a table read, Cumming recalled chuckling when another cast member mispronounced the Arizona city of Tucson–or so he thought. “I thought it was pronounced ‘tuck-son!’” he laughed. “I was mortified when I realized I had gotten it wrong!” 

Nevertheless, Cumming handily won over American audiences, playing not one but three iterations of Sandy Frink. The reunion dance sequence performed by Cumming, Lisa Kudrow, and Mira Sorvino, set to Cindy Lauper’s “Time After Time,” was nominated for an MTV music video award; the film routinely appears on lists of must-watch cult classics.  

When the WUSSY team invited Cumming to Atlanta for a screening, he requested we select Romy & Michele for the event, which he told us later he hadn’t seen on the big screen since it premiered. He was excited to revisit the film, especially because a sequel is officially in the works: in February, Mira Sorvino confirmed that Robin Schiff, who wrote the original based on her play Ladies Room, will pen a second installment bringing together much of the original cast. “It was such a big hit, and the fact that there hasn’t been a sequel is total Hollywood misogyny,” said Cumming. “A real fear of showing women getting older on screen.” Had it been a buddy comedy about two guys, he added, we’d have already been treated to six sequels. 

Romy and Michele received the pleasant condescension typical of films destined for cult followings—Entertainment Weekly called it an “amiable mess”—and heralded Cumming’s arrival in Hollywood as a versatile, genre-bending actor who could make magic out of nearly anything. Meanwhile, as his film career was unfolding on one coast, he was simultaneously exploding onstage on the other. In 1998, Cabaret moved to Broadway, and Cumming won a string of awards for that performance, including a Tony. American actors rarely manage to slalom between film and theater, but Cumming—who’s a Brit, after all—has always successfully maneuvered back and forth; for every fan who knows him for his film and television work, another is a devoted follower of his early stage plays and one-man cabaret concert tours. “I really do thrive on both mediums, but once you’ve had that visceral contact that you get with an audience [onstage], it’s difficult to stop doing it,” he said. “That connection, to me, is sort of the lifeblood of being an artist.” 

A stage performer at heart, Cumming has always preferred New York to Los Angeles. He met his husband, the artist and illustrator Grant Shaffer, through friends in the city; they now live in the East Village with their dog Lala, who enjoys celebrity status thanks to her stylish appearances on The Traitors. “When Cabaret transferred to Broadway, that’s what really made me fall in love with New York,” Cumming told me. He’s spent plenty of time in LA over the years, but says it feels like a “work town,” where industry talk consumes most of the socializing. “I think LA is what Hershey, Pennsylvania must be like!” he said. “Everybody in Hershey probably talks about chocolate all the time, and in LA it's really the same thing.” 

Cumming became a U.S. citizen in 2008 in order to vote for Obama, though he retains his Scottish passport and spends a good deal of time there, especially lately while filming The Traitors. To him, New York feels like a bubble outside the malignant forces besieging the rest of the country—a literal island off the coast of America, oriented, geographically and culturally, towards Europe.  “I really worry, with more and more people’s rights being taken away—women, people of color, gay and trans people’s rights,” he said. “But it’s been sort of galvanizing me to make sure that I fight hard, to use my voice as loudly as I can to stop this.” 

In the last few years, Cumming has toured the country with a series of cabaret shows, which often use music, dance and comedy to dive headfirst into the country’s most fraught issues. Audiences in red states generally embrace his provocative content, but you can never be too sure, especially in Florida: during a tour stop near Mar-a-Lago for his show Legal Immigrant, he told The New Yorker’s Rachel Syme, spectators became irate over Cumming’s message of America as a country of immigrants. “’Get on with the show!’” One man yelled at him. “And I went, ‘This is the show! You’re in it!’” Just before his visit to Atlanta this spring, he’d been back in Florida testing out a new show, Uncut, which features, among other themes, meditations on being uncircumcised. (Cumming is a vehement critic of the traditional practice, which is much more common in the U.S. than in Europe: “it’s genital mutilation,” he told me. “It should be banned.”). The show, he reported cautiously, had gone over well, though you can never be too sure in Florida. 

Cumming was thirty when he moved to America, so he has an outsider’s view of his adopted country’s savage politics. “I lived half my life in another, completely different environment, so I think I have a healthy perspective on things here,” he said. “It allows you to see that you can have more than two political parties, you can have political discourse that doesn’t end in violence.” Spending time back home in Scotland—progressive, woman-led, Brexit-denouncing, LGBTQ-affirming, climate change-believing Scotland—sometimes has Cumming longing to move back permanently. But every return trip to New York reminds him—and Grant, a longtime New Yorker—why they love it, and perhaps, by extension, the rest of its crazy neighbors on the mainland. 

“I’ll always be coming back and forth,” he said. “So as long as I’m doing that, I have to stand up.” 

“I've always been a combination of mischievous, provocative, and challenging…and also sort of cute.”

As an openly queer actor, Cumming’s standing up has always involved standing out. But while his genre-defying, gender-bending career is queer in the most bedrock conception of that term, perhaps the most striking aspect of Cumming’s long life in the spotlight is how handily he’s avoided being pinned to any specific version of queerness. 

“It used to be that if there was a queer character, they would have a problem–they had AIDS, or had issues with their family, but whatever it was, there was always a problem connected to a gay storyline,” Cumming said. “But I think eventually, the aim is just to have queer characters where that’s only one of the many interesting things about them. And I think we’ve still not quite got there.” 

Cumming has certainly done his part to nudge the world in that direction. When it comes to understanding an artist’s point of view, the work they write themselves generally offers the best insight; I find it thrilling that, when given the opportunity to make his own film, Cumming crafted one in which he plays a man in a complicated separation from his wife. 

The Anniversary Party, which came out in 2001, was Cumming’s brainchild with Jennifer Jason Leigh, with whom he wrote, directed, and produced the film. The pair also star as Joe and Sally, successful actors whose sunny Hollywood life is cracking beneath them. Sally’s reaching the has-been end of her glittering career, while Joe longs for London, and–more subtly–for a handsome young man who attends the anniversary celebration the couple throw in their glamorous mid-century home. Cumming and Leigh made the film on a shoestring, shooting it in a month with a cast of mostly their friends (though those friends included Parker Posey, Gwyneth Paltrow, and John C. Reilly). 

“It was this very personal thing because it was about real people that we knew, these things that we knew,” Cumming explained. “And we said very harsh things about ourselves in it and I think that’s what people resonated with.” It isn’t an easy film, full of the petty cruelties of a marriage on the rocks and the cold in-or-out arithmetic of Hollywood, but it has a deep and complicated heart. Cumming is wonderful in it, utterly at ease in the gray area between the intimacy of his marriage and the desire for what (or who) might exist beyond it. “We wanted [Joe’s] bisexuality to be an element without it being a sensational thing,” he said, “Without anyone really commenting on it.” In that way, it’s a gesture towards the world Cumming would like us to live in, the one he’s always found a way to live in himself.

“people just want to know if you like cock. And when you say yes, it kind of shuts them up a bit, suddenly they stop being so inquisitive.”

Several years before The Anniversary Party, Cumming was forced to navigate his queerness under the harsh light of the world we actually live in. In 1993, he and wife, the actress Hilary Lyon, divorced. Students together at drama school, they’d married in 1985, when Cumming was only 21; he’s said that he married young to escape his father and prove that, unlike his parents’ unhappy union, he could find genuine love. When their marriage collapsed in 1993, Cumming was devastated, but the ruthless British press was only too happy to exploit the news–especially when they caught wind that Cumming was dating a man. “The British tabloids were terrible,” he recalled. “They went to my mother’s house, my ex-wife’s house, trying to find out who I was seeing.” 

Cumming knew he liked men and women before he got married, and hadn’t felt any need to claim some specific identity–or even what that identity would be. “But I realized that to be coy invites speculation, so it’s better just to get it out there.” And so he got it out there, in true Alan Cumming fashion, by posing nude on the cover of OUT Magazine in 1999. “Exposed!” boasted the cover line, trailing over his bare leg.

“When it comes down to it, people just want to know if you like cock,” he laughed. “And when you say yes, it kind of shuts them up a bit, suddenly they stop being so inquisitive!” There was one unexpectedly inquisitive viewer: Conan O’Brien, who was sure the cover was not as modest as it appeared. “He thought my heel was one of my testicles!” Cumming recalled, amused. “He was very convinced.”

Outing himself allowed Cumming to shape the narrative around his queer identity, something few people got the chance to do in the ‘90s. And it’s something he’s done since with a similarly defiant insouciance: picking the roles he wants, the life he lives, playing with gender and sexuality, without adhering to anyone else’s idea of what a queer icon should be. 

“I feel we’re still fighting against this argument that if you’re an action star, you can’t be queer, or that a queer person can’t be an action star–we still get sort of boxed in,” he told me. “I feel the more people who are out there playing all these different roles, then people just think about it less and they get used to it.” 

When we chatted, Cumming was in Italy, shooting a cameo for the film Death Do Us Part, which he told me will feature a resplendently curly wig and a live iguana. Shortly after that, he was back in Scotland, preparing to shoot the third season of The Traitors, a show that has made him a household name for anyone in America he hadn’t already won over. Reality television host is a new title for Cumming, but one he’s adopted with gusto. “I’m the stern daddy of it all,” he told the outlet Puck. Even more than in most such competitions, the host is himself a central character: Cumming addresses the cast in satiny melodrama, his Scottish accent keyed up to match his lavish costumes. Many are Cumming’s own clothes, jeujed up with capes, kilts and other accessories by stylist Sam Spector, to turn him into, as he puts it, “a dandy Scottish laird.”

A remake of the British original, the concept of The Traitors is relatively simple–I call it “fancy mafia,” as the rules essentially follow the classic summer camp game of murder and intrigue–but it’s become a runaway hit, in part thanks to its casting concept: beginning with season two, all the contestants are former participants in other reality TV shows, from veterans of the Real Housewives franchise to competitions like Survivor and Big Brother. The format adds a layer of individual narrative control to the psychological dynamics of the game, which–combined with the gothic Scottish backdrops–makes for intensely watchable content. “Pure, evil, shout-at-the-TV brilliance,” crowed The Guardian. Cumming demurred from giving any details on season three, except to assure us that it would be as devilishly fun as the first two. “Oh, you’ll enjoy it,” he said, smiling coquettishly. 

But holding court over one of television’s most popular new shows is only one of Cumming’s projects at the moment, and there are plenty to come. He’s currently touring Uncut and has a production deal with NBC-Universal to give them first look on project ideas. He and Forbes Masson are working on a musical for National Theatre of Scotland, and there’s talk of returning to The Anniversary Party with Jennifer Jason Leigh. And of course there’s a Romy & Michele sequel to film soon. 

“I don’t really have a list of things I want to do,” he said. “I like to stay open to possibility.” For a performer as singular as Cumming, there was never any prescriptive list to follow anyway; the key to his success, perhaps, is the joy with which he’s charted his course without one. 

“It’s a liberating thing being my age and looking back, seeing the patterns of things,” he told me. “And I see that, through it all, the bolder I was, the more true to myself, the more people accepted me and respected my work.” If that is the general rule of Alan Cumming, then it does most certainly apply. 

Photographer: Jamie Hopper
Photo Assistant: Landri Peirce
Stylist:  Joey Ellington
Hair and Makeup: Lauren Killip
Location: The Hotel Clermont // Atlanta, GA

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