Quality Trash

The first time I spoke with Ron Oliver, on a video call in May, I was expecting flamboyance writ large. This is, after all, the man they call “Daddy” on set—a nickname that squeaks by as appropriate only because he’s the platonic ideal of a Palm Springs gay. Take his home: a mid-century bungalow in the coveted Racquet Club Estates with multiple tiki bars and an extensively applied martini motif (there’s one tiled into his in-ground pool and another emblazoned on a flag that flies full-mast when he’s home for happy hour). In photos, Oliver’s bald head and expressive eyebrows bob above colourful suits patterned like wrapping paper, the most elaborate of which features rows of snowflakes and reindeer. On social media, he refers to himself as “Sir Ronald,” a nod to the knighthood he bought in exchange for a $500 donation he bestowed upon Sealand, the micro-nation off the coast of England.

Knowing all this, I was mildly disappointed when I logged on to see him wearing a resort shirt (even if it was covered in stills from Hitchcock movies). Oliver had slept just five hours a night for the previous six weeks, leaving little energy for grand sartorial gestures. He was taking my call from a hotel room in Sofia, Bulgaria, where he was wrapping up pre-production on a series of Hallmark movies he’s dubbed his “epic.” Modelled on Hallmark’s popular Wedding Veil hexalogy, The Groomsmen consists of three films, The Groomsmen: First Look, The Groomsmen: Second Chances and The Groomsmen: Last Dance. Each follows one of a trio of best friends as they navigate the hurdles that come with securing wedded bliss—except, this time, the wedding stories are told from the male perspective. Anywhere else, this would be an unremarkable twist. But, at Hallmark, a cable TV network and streamer that’s notorious for churning out cookie-cutter content, any microscopic innovation is genre-bending.

Three weeks of pre-production is standard for Hallmark flicks, and Oliver was preparing to direct three feature-length movies in only twice that amount of time. A sizable challenge, but one he’d been training for, having written or directed 34 Hallmark movies since 2007. His days were spent scouting locations and auditioning cast members across Bulgaria, Greece and the UK for the series’ breakneck shoot. Filming was set to start in two days. On our call, however, he seemed most concerned with rewriting the screenplays, which he’d been doing in the production van and at the hotel late at night. “It’s been hectic,” he says, “because the scripts they had weren’t very good.”

Hours later, I’m still mulling over that last comment. I’ll admit to being a seasonal Hallmark viewer, but—and this is key—for the purpose of mockery only. The company’s Christmas starts indecently early, rolling out in mid-October, before most people have even carved their jack-o’-lanterns. I usually wait until after the first snowfall to engage. That’s when my best friend and I break out our Hallmark movie drinking game, which, over the years, has expanded to include 61 rules. They reference the quintessential building blocks of a Hallmark plotline. No. 11: A crucial work deadline falls on Christmas Day. No. 29: A big-city girl lands in a small town. No. 42: A would-be couple find themselves under the mistletoe. No. 15: A small or failing business is saved. The rules aren’t strictly enforced, of course. If they were, we’d be drunk before our turtleneck-clad heroine stumbled upon her puffy vest–wearing love interest. Even just taking a sip every time we see multiple Christmas trees in one room (rule No. 3) would put us at serious risk of cirrhosis.

And yet, despite the many hours I’ve spent in the Hallmark Cinematic Universe, it had never crossed my mind to consider whether the scripts were any good, in the same way I never stopped to consider the quality of reality-TV staples like Love Is Blind or Vanderpump Rules. I don’t come to Hallmark looking for artistic expression or edification; I come to gawk at other people’s poor decision-­making and wonder at a world that can sustain such astronomical levels of heteronormativity. Hallmark movies are, well, schlock—famously predictable, corny and cloyingly sentimental, the subject of at least one SNL spoof and countless memes. And though Hallmark is loath to acknowledge its so-bad-it’s-good appeal, I can’t be the only member of its audience watching ironically. So the idea of Oliver sitting up nights labouring over Hallmark scripts implied an unexpected level of earnestness about the company’s content.

It’s precisely his ability to take schlock seriously that has made Oliver the king of Hallmark. His movies are cheesy, but he understands cheese better than anybody, which is how he pulls off the near-impossible task of injecting glimpses of real human emotion into his films. Hallmark has so far resisted the death of network TV, but streamers like Netflix and Prime have been edging into its territory with ratings juggernauts like The Princess Switch trilogy and Candy Cane Lane. In response, Hallmark has given Oliver a vital assignment. In an attempt to hold on to its audience share, the company famous for embracing quantity over quality is shifting gears, and the Groomsmen trilogy has been tapped for the vanguard. After all, Oliver has spent almost two decades lifting Hallmark out of cable obscurity and turning it into an inescapable cultural phenomenon. If anyone can inspire a new respect for Hallmark movies, it is, perhaps paradoxically, the reindeer-loving Daddy staring back at me.

No one forgets meeting Ron Oliver. The flashy outfits are a factor, but he also has a charming man-about-town quality that has won him legions of friends and fond acquaintances. In September, when he was in Vancouver doing post-production for The Groomsmen, I met him in the bar of the Wedgewood Hotel. As I walked in, Oliver was chatting with the bar’s piano player, who, for the next hour, played movie themes in Oliver’s honour. While ordering us martinis—Aviation gin, a vermouth rinse and orange bitters; shaken, not stirred; with ice and garnished with three blue cheese–stuffed olives—Oliver teased the server for shaving off the moustache he usually wore. The day before, Oliver visited the spa at the Fairmont Hotel Vancouver, where he’s been seeing the same facialist for 15 years, and the Shameful Tiki Room, where he used to get his mail delivered when he was in the city.

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Making cheap movies look less cheap has turned Oliver into a lucrative asset. These days, he’s Hallmark’s number-one fixer

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In his sharkskin suit, martini-shaped tie clip and pocket square, popping olives into his mouth with impressive dexterity, Oliver looked the consummate bon vivant. He’s come a long way from the corn-fed kid born in small-town Ontario in 1960. Oliver was raised in the village of Dundalk until his family moved to New Lowell, 45 kilometres east, when he was nine. New Lowell was just a couple of thousand people scattered around one main intersection and community centre. It wasn’t the kind of life Oliver’s parents had envisioned for themselves. In the 1950s, his mother, Helen Elizabeth Smith, had plans to hitchhike to New York and pursue modelling. Then she met George Oliver, a rockabilly singer, at a community centre in Avening, Ontario. Helen gave up her Big Apple dreams to date George, and when her parents balked at the idea of their daughter marrying a performer, George took the hint and quit singing. By the time baby Ron came around, Helen was a housewife and George a provider, first as a real estate agent, then as an insurance broker and finally as the proprietor of a boat-building company.

Oliver struggled to jam himself into the round hole of rural Ontario. “I came out of the womb gay,” he says. “If she’d spent five minutes with me, even Helen Keller would have known I was gay. How do you express that in a small town in Ontario in the 1960s? You don’t.” As a pre-teen, ­Oliver was unathletic, partial to puffy satin shirts and three-piece suits, and uninterested in the horses and turkeys that his younger sisters kept on the family’s hobby farm. It was unlikely he could have passed as a farm boy even if he’d tried. Besides, he was much happier reading Tales From the Crypt and watching horror movies on CKVR out of Barrie. The films mostly aired after his bedtime, but 10-year-old Oliver made a deal with his mom: if he went to sleep at 9 p.m., she would wake him up at midnight, just in time for ­Frankenstein or Creature From the Black Lagoon. She’d tuck him back into bed afterward, around 2 a.m., and all told he’d get enough sleep to be ready for school the next morning.

Three years later, Oliver stumbled across a TV ad for The Rocky Horror Picture Show. It was horror, but the monster had a full face of makeup. As Dr. Frank-N-Furter declared himself a transvestite and made out with nerdy Brad Majors, Oliver realized for the first time that he was not the only queer boy on planet earth. “It was like a smoke signal sent from space,” he says. “I remember going, ‘Holy crap. There are other people out there who are just like me.’” But there was little he could do in his town to join the Tim Currys of the world, so Oliver spent his free time making short films using his school’s Super 8 camera. In one, his sisters’ Barbie doll walked up to the door of her Dreamhouse to find Ken’s bloody head on the ground. Oliver was nursing a career ambition that would get him the hell out of New Lowell: writing and directing horror movies.

It wasn’t the last time Oliver would find himself unsuited to his surroundings. When he arrived in Toronto in 1984 at the age of 24, New Wave cinema was on the rise. Young filmmakers like Atom Egoyan, Don McKellar and Patricia Rozema were banding together to reject formulaic genre films and create a uniquely Canadian cinematic culture. Oliver, on the other hand, looked and acted like he’d just flown in from Hollywood. He wore sports jackets and had swooping blond hair, and he wanted to make films that people would watch, not ponder. His boldness ultimately served him—after mailing out a few of his scripts, he landed a full-time screenwriting job at a company called Simcom. They’d recently had great success producing Prom Night, a slasher starring a 22-year-old Jamie Lee Curtis, so they green-lit a script Oliver wrote about a high school haunting, which was eventually rebranded as a sequel and called Hello Mary Lou: Prom Night II. Oliver intended for the movie to be campy, but the director struggled to execute the tone. Simcom tapped Oliver, who had no directing experience, to handle roughly $100,000 worth of reshoots. With all the brashness of a young upstart, he cold-called slasher god Wes Craven for advice. “It’s really easy,” Craven told him. “Think of your audience. You give them a scare, you give them a hard-on and then you send them home.”

The final product was a meandering picture about a dead prom queen who haunts her former school and the jilted beau who accidentally lit her on fire (he’s now the principal). It’s The Exorcist meets Carrie meets the video for “Total Eclipse of the Heart,” complete with a few racy scenes and a highly discomfiting father-daughter kiss. (In 2019, Charlize Theron would quip on the movie podcast How Did This Get Made? that she’d seen hard-core porn less horny than this movie.) Hello Mary Lou, which Oliver considered high camp, was received as schlock. Just as the original director had struggled to understand Oliver’s vision, so did Toronto’s movie critics. “It’s enough to make you sick,” wrote Rob Salem for the Toronto Star. “Once upon a time, this sort of low-budget formula quickie was just about the only thing you could get produced in this country. That no longer being the case, one wonders how something like this managed to slip through the cracks.”

“It was like we filmed puppies being drowned or something,” says Oliver of the critical reception to the movie, which is now a cult favourite. “Is it a perfect film? Far from it—but it’s fun.” He was dejected until a fax arrived at the Simcom offices with a review from the LA Times that called Hello Mary Lou the Blue Velvet of high school horror. “I remember sitting back down at my desk and thinking, I’m going to move to America—because they understand the sensibility of quality trash.” He did exactly that in 1989, but even in West Hollywood, Oliver struggled to get a foothold. Mostly, he flew back to Canada to direct episodes of TV shows like Are You Afraid of the Dark?, in which he cast a 14-year-old Ryan Gosling, and Goosebumps, also starring Gosling. (The two became close during filming, and the actor later stayed with Oliver when he was in LA for auditions.)

It was on one of these trips to Toronto that Oliver met Anthony Bernardo, a financial consultant. What was originally a hook-up turned into a passionate romance. In 2000, two years after they met, the couple had a marriage ceremony at Yamashiro, a Japanese restaurant and erstwhile celebrity haunt in the Hollywood Hills. But work took Oliver out of town for months at a time, and in 2003, he came home to find a note on his own Tiffany stationery: Bernardo had taken his things and left. For a week, Oliver lay by the pool in his Palm Springs home, Jack Daniels in hand, Frank Sinatra crooning in the background. “I told myself I would never fall in love again,” he says. “Love was crap.”

By this time, he’d also sworn off TV shows, which he found creatively constricting. So, with no husband waiting at home, he took on every feature-length film he was offered. When he got a call from a former colleague in 2007 to direct Bridal Fever, about a chronically single book editor on the hunt for “the perfect guy,” it was a quick yes. To him, this was just another made-for-TV movie, and he rarely gave much thought to where his movies aired. No one could have known that this particular channel—Hallmark—was about to begin a precipitous ascent.

When Bridal Fever was released, working for Hallmark was considered a dead end. “I thought Ron was crazy—he had so much talent,” says Tom Lynch, a producer who’d worked with Oliver on a number of successful kids’ series, including The Secret Life of Alex Mack. “At that time, you went to Hallmark to die.” The company, primarily known for its century-old greeting card business, was a minor player in cable TV under its subsidiary, Crown Media (since renamed Hallmark Media). The Hallmark Channel aired low-stakes syndicated content (Little House on the Prairie, Matlock), with occasional made-for-TV flicks wedged in between. The movies, though spearheaded by independent producers, embodied the same principles as the company’s cards—wholesome, sentimental and focused on small-c conservative life milestones like weddings.

Then, in 2009, Hallmark Media hit two milestones of its own. It anointed a new CEO, Bill Abbott, its former VP of ad sales. Abbott had presided over a massive period of growth: during his nine years in that role, the Hallmark Channel’s ad revenue had ballooned from $10.2 million to $223 million. Then the company strung together four original holiday movies under the now-famous banner Countdown to Christmas. The Yuletide assault was such a success that Abbott doubled down on tinsel and mistletoe, and by 2013, Hallmark was shamelessly hawking Christmas in July programming. Between 2000 and 2023, the channel released 424 Christmas films—31 of them during 2023’s countdown alone. That’s not to mention some of the other seasons (real and invented) that now make up the company’s content calendar: Spring Into Love, Summer Nights, Fall Into Love, New Year New Movies and Loveuary.

As the Hallmark industrial complex was taking off, Oliver faced a decision. After Bridal Fever, he was on the company’s radar, and the offers started rolling in—they needed more directors to keep up with demand. By then, Oliver had made a few weightier films, including a thriller starring Shannen Doherty and a film-noir flick that billed itself as having America’s first gay detective. They’d all flopped at the box office. If he couldn’t be a director who made political statements or breakthrough indies, thought Oliver, by god he would be a working one. So when Hallmark’s producers came calling—and calling—he kept answering.

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“I’d step out of my trailer in Greece and yell, ‘Anybody here have the number-one Netflix movie in the world? Anybody? Oh, just me’”

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By 2014, Oliver was spending most of his time writing or directing for Hallmark, making upward of four movies a year. Schedules were tight and budgets were slim, averaging roughly $3 million per production. Oliver’s canon of McMovies—with titles like Perfect on Paper, My Christmas Dream and Recipe for Love—was rapidly growing. Work ethic aside, Oliver has thrived at Hallmark because he understands genre films. He sees Hallmark movies for what they are—not poorly executed rom-coms or failed attempts at originality but reassuringly predictable little yarns. In its purest form, the Hallmark formula goes like this: the protagonist is a career-driven woman played by an actor whose heyday has passed (Candace Cameron Bure from Full House or Lacey Chabert from Mean Girls, say). Her job is wholesome and ­unthreatening—baker, maybe art historian. In the first five minutes, the major plot points are established: she’s single and struggling professionally, and she stumbles upon a dude who is handsome in a Gap-ad kind of way. They get off on the wrong foot before being thrust together in service of some project, possibly related to a small business or the town’s Christmas tree.

The movies are constructed in nine acts, revolving around eight commercial breaks. The meet-cute, for example, comes at the end of Act One, and Act Four ends with the would-be lovers sharing pivotal information about their pasts. Act Eight introduces a seemingly irresolvable conflict that is, in fact, resolved in Act Nine. Other probable elements include the heroine’s less-hot BFF, the leading man’s saucy ex-girlfriend and no more than two significant Black characters. And then there’s the couple’s first kiss, which in no way involves tongue. It occurs seconds before the credits roll, absolving the network of any responsibility for the sex that may follow.

Hallmark’s commitment to this paint-by-numbers approach extends to its characters’ appearances. “They’re very picky about wardrobe,” says James Wilberger, a frequent Hallmark producer. “They have to approve every outfit before you can put it on camera.” Trendy pieces like cropped sweaters are usually a no, and low necklines are approved on a case-by-case basis. (Once you know this, it’s startling how many fully buttoned-up cardigans you’ll notice.) At a post-production session in Vancouver for the Groomsmen trilogy, I watched Oliver spend three conference calls going back and forth with Hallmark executives about whether they could, for a single scene, add a few grey hairs to some of the actors’ heads and fill in the lead’s eyebrow scar. Though the matter was left unresolved, one of the execs called the issue “hugely important.”

While haggling over scar tissue may seem trivial to people not on the company’s payroll, these guardrails are in place to protect the very thing Hallmark audiences crave: the guarantee that, for the duration of each film, life is wholesome and every conflict is swiftly resolved. Strife is born of misunderstanding, not disagreement. People may be self-absorbed, but they are never ill-intentioned. And decades-long family estrangements can be settled in a single conversation. People who fall in love always end up together. Sure, it’s straight, white and almost comically vanilla, but it’s a happy-ending world where challenges invariably bring out the best in people instead of the worst. The Hallmark universe may be manufactured, but given today’s divisive political climate, environmental crises and rising global instability, aren’t we allowed a little powdered hot chocolate once in a while?

Instead of lamenting the restrictions set by his employer, Oliver focuses on making infinitely watchable movies—and having a ball doing it. On set, he quotes old-school directors like Hitchcock, asks for physical comedy in the style of Jerry Lewis and blasts everything from Sinatra to “Murder on the Dancefloor.” No one I spoke to had ever seen him lose his temper. “It’s definitely the Ron show,” says Jonathan ­Bennett, who played heart-throb Aaron in Mean Girls and is now one of the leads in the Groomsmen series. “And it’s a fun show to be a part of. I think that’s why his sets run so smoothly.” The merrymaking, though genuine, is a screen for Oliver’s greatest skill: balancing logistics and personalities without looking like he’s expending any effort at all. He can discuss de-aging technology in detail with a colourist, then turn around and promise his executive producer margaritas while talking her out of a list of editorial demands. When faced with the fiscal challenge of making a cocktail party scene bustle with the six extras his budget allows, he decides to pan between two conversations while the extras walk through the shot at ­intervals—a feat of penny-pinching stagecraft.

Making cheap movies look less cheap has turned Oliver into a lucrative asset. These days, he’s Hallmark’s number-one fixer, and he’s among the highest-paid directors at the company (just how well paid he’s contractually forbidden to tell me). Everyone seems to agree he’s worth it. “He gets assigned to the higher-profile Hallmark movies,” says Allen Lewis, the producer of the Groomsmen trilogy. “They need to be elevated.” Many of Oliver’s recent Hallmark films were high-­investment projects, like The Christmas Train, which featured bona fide household names Dermot Mulroney and Joan Cusack. It had a whopping (by Hallmark standards) budget of $7.5 million. “I also bring him on to projects when I know they’re in trouble,” says Lewis. As a writer-director, Oliver can rehab a troubled script and film it quickly, a skill that has scored him plum assignments. After he posted a selfie at the Plaza Hotel in New York on Instagram, Hallmark executives asked if he wanted to make a Christmas movie set there. Released in 2019 and a fan favourite, Christmas at the Plaza was partially filmed at the actual hotel. For Oliver, it was a chance to write and direct a love letter to his new husband, Eric Bowes—whom he threw an engagement party for at the Plaza and married on Christmas Day in 2013.

Oliver is unabashedly obsessed with the holiday season. He’s been known to tear up just talking about Christmas, and each year he throws a multi-day ­celebration for dozens of family and friends at his home in Palm Springs. His mother used to travel in from Creemore (Oliver’s parents split up in the 1980s), and by 2018, he was devising a plan to move her out to California permanently. But, before he could implement it, Helen suffered a stroke and died three days later. Devastated, Oliver distracted himself by returning to work and pouring his grief into a new Hallmark property, Christmas Everlasting. In the movie, which Oliver directed and co-wrote, a big-city lawyer named Lucy learns of the death of her sister, Alice, and has to go back to Wisconsin to settle her estate. There, the protagonist grapples with her guilt at having spent so much of her life away. “I wasn’t there for her,” Lucy says. “I haven’t been for a long time.” In the end, she’s absolved—by her love interest. “Don’t blame yourself,” he tells her. “Alice never did. She was so proud of you, of everything you’ve done, of everything you are.” It’s unexpectedly moving. Of all the Hallmark movies I’ve watched, it’s the only one that’s made me tear up. The emotional core didn’t feel trite or contrived. There was something that was, in fact, irreparable. There was actual loss.

For all his bravado, Oliver believes in the messages that form the foundation of Hallmark movies: that Christmas is a time of generosity and forgiveness, that love brings out the best in people, and that people are, on the whole, good. The climactic monologues are predictably banal, but at least the sappiness is authentic—what they may lack in originality, they make up for in integrity. It’s this ineffable quality that distinguishes Oliver’s films from the hundreds of other Hallmark pictures. And although audiences cannot possibly be as optimistic about the world as Oliver is, clearly they want to be.

Sidestepping Hallmark entirely is a challenge, even for the rom-com averse. By 2018, Countdown to Christmas had made Hallmark the most watched channel for (mostly white) women between the ages of 25 and 54. Then Covid came along, slammed the world shut and created a captive, connection-­starved audience. Just nine days after the World Health Organization declared a pandemic, Hallmark was swooping in to capitalize on our desperation for even second-hand love. On March 20, it aired a surprise marathon, We Need a Little Christmas, for fans isolating at home. The move paid off: in the fourth quarter of 2020, Hallmark was the number-one American entertainment cable network. The following year, Forbes reported that the Hallmark Channel was earning more than $1 billion a year in ad revenue, on top of other sources such as streaming subscribers and international distribution rights. (The company, which is privately owned, declined to answer questions about its finances.)

As viewership grew, so did Hallmark’s place in the cultural zeitgeist. On SNL, Scarlett Johansson played a bachelorette on a Hallmark dating show called A Winter Boyfriend for Holiday Christmas, in which she’s asked to choose between a hometown boy with a struggling Christmas tree farm, the prince of a fake European country and Santa Claus. Gwen Stefani stepped in as guest DJ on Hallmark Channel Radio, sharing a playlist of her seasonal favourites. AMC’s ratings darling Fear the Walking Dead got whomped by Oliver’s movie A Timeless Christmas, which drew a same-day audience of 3.4 million viewers. Dozens of podcasts and innumerable online forums began to surface, giving devotees a place to dissect the chemistry between lead actors and gossip about filming locations.

Hallmark’s success begat imitations, especially as the company was rocked by scandal. In December of 2019, the network aired a commercial for Zola, a wedding planning company, that featured a lesbian couple (gasp!). The ad triggered a wave of conservative pushback, including a boycott threat from the fundamentalist Christian group One Million Moms, prompting CEO Bill Abbott to remove it—which in turn provoked a surge of complaints from liberal viewers and advertisers. The left and the right were in a tug of war for the soul of the Hallmark Channel, and in the end, Abbott was forced to resign. While Hallmark was flailing between demands for diversity and pacifying its traditional viewers, other streamers upped the ante. Channels like Lifetime and ABC had been making Hallmark-ian flicks for years, but bigger fish like Netflix, Peacock and Prime were starting to catch on. In 2018, Netflix aped a Hallmark sub-genre, rom-coms with royals, with The Princess Switch, starring High School Musical alum Vanessa Hudgens. The streamer then followed up with two sequels, The Princess Switch: Switched Again and The Princess Switch 3: Romancing the Star. Hallmark-indebted content has since become so ubiquitous that the term “Hallmark movie” refers to almost any made-for-TV rom-com—the brand has officially joined the ranks of Kleenex and Band-Aid. In 2023 alone, there were a whopping 103 new holiday movies released across 15 television networks and streamers.

Oliver has profited handsomely from this ­dispersion—many of the films in question are made by the same producers he’d been working with at Hallmark. “Every time I receive an order to make a Christmas movie for a new company, my first call is to Ron,” says Brad Krevoy, who produced the Oliver-directed Hallmark pics A Christmas Detour and Every Christmas Has a Story. “He understands the holiday genre better than anybody.” When Netflix green-lit a project in 2020 called Falling for Christmas, about a woman who gets amnesia after a ski accident, Krevoy hired Oliver to do rewrites. The same day Oliver signed on, Lindsay Lohan agreed to star. It would be the beloved Y2K starlet’s first leading role since 2013. The film’s budget was set at just south of $15 million—making it Oliver’s most high-profile project to date. In the end, Oliver’s contributions were substantial enough that he got a shared writing credit.

Falling for Christmas came out in November of 2022 and was viewed more than 31 million times in its first four days of streaming. Oliver, who was directing the sixth instalment of the Wedding Veil series in Greece at the time, took every opportunity to brag: “I’d step out of my trailer and yell, ‘Anybody here have the number-one Netflix movie in the world? Anybody? Raise your hand! Oh, just me.’” The success of the film catapulted him to a new level of renown: he was the man who had helped launch the Lohanaissance. His co-writer credit appeared in Times Square, and the LA Times dubbed him “Mr. Christmas Movie.” And yet, when I broach the subject with Oliver, he seems squeamish about being credited for ushering Hallmark’s holiday formula into the mainstream. “I was also making comedies for Universal,” he reminds me.

Outside of his Hallmark films, Oliver has found a lucrative niche making sequels: Grand-Daddy Day Care, Bigger Fatter Liar. He insists that it never felt like he was making a lot of Christmas movies—an unconvincing claim from a man who’s made dozens. It seems like he’s experiencing a sensation not unlike what one might feel after bingeing a few of his movies. It’s fun while it’s happening, but afterward, we crash down to reality—our dissatisfying jobs, our dysfunctional relationships, all the non-­happily-ever-afters of our IRL lives. It’s normal, even healthy, to escape our stressors for a few hours at a time. During the Great Depression, movie theatre attendance went up even as people’s bank balances went down. It was worth that hard-earned 25 cents for a break from it all. The worse the world, the more we crave time away from it.

The Groomsmen series is a pillar in the relaunch of Hallmark’s streaming platform, which was recently re-christened Hallmark Plus (zero points for originality) and aspires to be more cinematic and less made-for-TV. That’s not the only watershed moment: the Groomsmen series will also include Hallmark’s first film about a gay wedding, a landmark event for a company known for adhering to conservative Christian morals.

As for Oliver, he had sworn off Christmas movies entirely, citing a saturated market, until Netflix rang him up in July and offered him a rewriting gig. His flip-flop is happening at a time when he’s accomplished enough to think about his legacy. “There’s always going to be that question of, Do I wish I’d made Schindler’s List? Do I wish I’d made some deeply touching artistic piece that has merit and cultural importance?” he tells me. “The answer is that it doesn’t matter if I wanted to—I couldn’t. It’s not in my DNA. And I don’t know that I’d be any happier if I had. I don’t know how I can get any happier than this.” It’s hard to argue with his logic. There was a time, back in New Lowell, when Oliver thought he was destined to marry a hometown girl and lead the life his parents had chosen. Now, his days are full of things he loves—his husband, his home in Palm Springs, his suits, his martinis, his film sets.

I ask whether it bothers him that some people think of his movies as schlock. “People have said terrible things about my movies,” he says. “I prefer to go with the people who say nice things, because I don’t need to feel horrible about myself.” At the airport for one of his recent flights to Bulgaria, a woman at the check-in desk started tearing up while Oliver spoke with her. Apparently her mom, who has Alzheimer’s, had lit up watching The Christmas Train. “Do I want an Oscar? Sure—who doesn’t want an Oscar? But do I also want a hug from a clerk at the airport, because she loved my film and it touched her? I’ll take that any day.”

The critical consensus is that Hallmark movies are bad, yet Oliver is delivering a product that is working exactly as it was meant to: his audience is transported and entertained. If a product is cheesy by design, is its cheesiness really a failure? It’s difficult for me to imagine being so inspired by a Hallmark film that I would hug a stranger in an airport—though I can’t remember the last time I felt compelled to hug a stranger period. Perhaps my inclination to mock Hallmark movies, to retain some semblance of cool cynicism, is locking me out of the catharsis millions of people experience while watching Oliver’s films.

There’s a scene in Christmas at the Plaza where the heroine is unburdening herself over a candlelit dinner with her love interest. “When I first started out at university, I had all these really lofty goals, you know?” she says. “I wanted to use my education to speak to the human condition. Maybe make a difference in the world.” She admits to having thought she would do something more important with her life than cataloguing Christmas ornaments for a hotel. “But think about it this way,” her studly companion replies. “You’re going to bring happiness to who knows how many people this Christmas. What’s more important than that?”

Maybe we don’t need to judge ourselves for wanting to indulge in cozy seasonal tableaux, the early moments of falling in love or a nice, uncomplicated resolution. Not every film needs to change the world in order to be, in its own way, good. Maybe it’s worthwhile for it to just be enjoyable and return us to our lives a little more hopeful than we were 90 minutes earlier. So this year, I’ll continue my Hallmark tradition—and if I manage to lose myself in the drinks, or the company, or the movie itself, even just for a moment, I’ll try to uncritically welcome the reprieve.

This story appears in the November 2024 issue of Toronto Life magazine. To subscribe for just $39.99 a year, click here. To purchase single issues, click here.