Cruel Intentions star Sean Patrick Thomas: ‘I keep my MTV Best Kiss award in my man cave’

Now returning to the universe of the scandalous 1999 teen movie in its new TV spinoff, the ‘Save the Last Dance’ actor speaks to Adam White about his Y2K fame, being dazzled by Denzel Washington, and what it was like to be one of a handful of Black actors in Nineties high school films

‘When we did the film, we all thought, “Oh, this is fun, this is crazy.” Then you have kids and you’re, like… oh my God! Is this what’s going on at school?’ (Getty)

Sean Patrick Thomas, teen movie king of the late Nineties and early Noughties, is showing me an object far more impressive than any Oscar or Grammy: his MTV Movie Award for Best Kiss. “It’s right here!” the actor beams, after scurrying off camera to grab it. He’s in what he terms his “man cave”, the award stuffed beneath his big-screen TV and near his gym equipment. Thomas holds the popcorn bucket-shaped trophy up to his camera lens. It is, I tell him, almost stupidly large. “And heavy too!” he shoots back.

He won the Best Kiss award in 2001 for locking lips with Julia Stiles in the seminal romantic drama Save the Last Dance. To put into perspective the significance of this award – to anyone not raised on a cinematic diet of Freddie Prinze Jr, Rachael Leigh Cook and Jennifer Love Hewitt – Thomas and Stiles won it a year after Sarah Michelle Gellar and Selma Blair, for their saliva-riddled smooch in Cruel Intentions, and four years before Ryan Gosling and Rachel McAdams took home the prize for The Notebook.

Thomas was also in Cruel Intentions. He was not in The Notebook. But considering how magnetised he was to a particular era of coming-of-age cinema, I wouldn’t be surprised if he was a background extra. Back then, he was a jock in the high school party movie Can’t Hardly Wait, got his head crushed by Michael Myers in the teen slasher flick Halloween: Resurrection, and cameoed in the cult-classic genre spoof Not Another Teen Movie. Thomas also has a long list of modern credits (he currently stars in Prime Video’s superhero series Gen V, and appeared in Joel Coen’s spellbinding 2021 film adaptation of The Tragedy of Macbeth with Denzel Washington), but it’s the teen films of yesteryear that people (OK: me) are most eager to ask him about.

Admittedly, this is not helped by Thomas’s latest project: Prime Video’s new TV revival of Cruel Intentions, which transplants the teen deviance of the original 1999 film to an era of iPhones and Olivia Rodrigo. “I’m kind of amazed that the movie has had so much staying power,” Thomas says. “This thing had legs!”

He plays a different character to the one he played in the film – music tutor there, university professor here – but his storyline is deliberately similar. He is introduced as one of the show’s sole good eggs, which means corruption – by quasi-incestuous step-siblings, naturally – awaits. And while the new series doesn’t quite scratch that same naughty itch as the original movie, it’s always at least mildly indecent. There’s political intrigue, sorority house intrigue, lots and lots of naked butts.

In the original Cruel Intentions, itself a Nineties spin on the 18th-century French romp Les Liaisons dangereuses, Thomas played kindly Ronald, who is – along with a virginal good-girl played by Reese Witherspoon and a borderline-incompetent naif played by Blair – embroiled in an elaborate game of sex and seduction engineered by Gellar’s cocaine-snorting prep schooler Kathryn Merteuil. Ryan Phillippe was Kathryn’s bad-boy stepbrother Sebastian; Joshua Jackson his bitchy bestie with a penchant for carnal blackmail. American Pie’s Tara Reid was also in the fil because this was 1999 and Tara Reid was in everything back then.

It was rare then – and now, I think – for a Black man to lead a studio film that is number one at the box office. That’s a huge thing that I’m very, very proud of

It was only Thomas’s second proper movie, and he remembers the set being “playful”, with everyone giggling in between takes. “We were just… ‘Whoa, I can’t believe we get to do this,’” he says. “Ryan and Reese were a couple at the time, so it was nice to be around all that young love. I wasn’t particularly knowledgeable about Buffy the Vampire Slayer at that point, but I obviously knew who Sarah was – any feelings of intimidation went away within 10 seconds, though. She was just so cool, down to earth and ready to play.”

A big part of the movie’s appeal – it grossed $76m (£60.4m) at the box office, spawned two direct-to-video sequels, two aborted TV spin-offs and inspired a jukebox musical – was its fresh-faced salaciousness. You couldn’t quite believe a bunch of 16-year-olds were being so horrible to one another. For the Thomas of today, though, this thought is terrifying. “When you’re a dad, you look at everything differently,” he says. He has two children, aged 16 and 14. “When we did the film, we all thought, ‘Oh, this is fun, this is crazy.’ Then you have kids and you’re, like… oh my God! Is this what’s going on at school? What are they hearing or talking about at choir practice? I hope this is not anything close to real life…”

Now and then: Thomas in the new ‘Cruel Intentions’ TV show (left), and in the 1999 movie (Prime Video/Shutterstock)

The 53-year-old is at home in Los Angeles. Thomas is funny, earnest and, honestly, kind of annoyingly ageless – I think I spy a spot of salt and pepper in his facial hair, then realise it’s a trick of the light.

Early on, he trained in drama at the University of Virginia before finishing his acting studies at New York University, graduating in 1995. Shakespeare was his first love. “I did a scene from Twelfth Night in a class, and the language, right off the bat, just seemed to roll off my tongue. I seemed to understand it without trying too hard, you know? I just ate it up.” By 1996, he was starring in the action drama Courage Under Fire alongside Denzel Washington. “When I watch myself in that now, I can tell I’m just in a daze,” he laughs. “I was absolutely sitting there watching Denzel more than I was actually doing my work.”

He moved to Los Angeles soon afterwards, arriving in the midst of a boom in film and television aimed at and starring teenagers – or, well, twentysomethings pretending to be teenagers. And, for the most part, white twentysomethings. “It was a period of time where it seemed like me and, like, [She’s All That’s] Dulé Hill and [10 Things I Hate About You’s] Gabrielle Union and maybe a couple of others were the only Black people in those movies,” he recalls. “There wasn’t a whole lot of room for introspection about it, though. If somebody offers you a job, you take it because you’re trying to build your career. You’re trying to get your hustle on. It’s only after it’s all over that you can look back and say, like… wow, they only gave a handful of us a shot. I’m just grateful I was one of them.”

He later mocked this very thing in Not Another Teen Movie. In it, a Black character played by Scream 3’s Deon Richmond finds Thomas drinking beer in the kitchen of a house party and reminds him that he’s meant to be the only Black guy at that particular event. “My bad,” Thomas’s character replies, with total sincerity. “Honest mistake!” deadpans Richmond.

“At the time I didn’t know if I wanted to spoof myself,” Thomas laughs. “Because that stuff lives forever, you know? But then I thought, OK – what the heck? Somebody sent it to me recently. It’s still funny!”

Best kiss: Thomas and Julia Stiles at the 2001 MTV Movie Awards (Shutterstock)

Of that period, he has the most love for Save the Last Dance, in which Stiles unlocked heretofore unthinkable levels of whiteness as an aspiring dancer who moves to inner-city Chicago and falls in love with Thomas’s Derek. “When I first got the role, I didn’t feel confident about it,” Thomas recalls. “I was 28 or 29 at the time and the character was supposed to be 18. I’m certainly no dancer at all, and the character had this urban background that I didn’t have, either. I felt awkward, but I took it one day at a time and just did the work. And, on top of that, it was rare then – and now, I think – for a Black man to lead a studio film that is number one at the box office. That’s a huge thing that I’m very, very proud of.”

He is, more than anything, grateful. “This is a very, very hard business,” he says. “The peaks and valleys, all of that. So to have even one project that people remember is a miracle, you know? But it really has been just a happy accident. I’m just extremely lucky.”

Sure. But they didn’t just hand out those Best Kiss trophies for nothing.

‘Cruel Intentions’ is streaming on Prime Video