YEAR: 1999
DIRECTOR: Roger Kumble
KEY ACTORS: Ryan Philippe, Sarah Michelle Gellar, Reece Witherspoon, Selma Blair
CERTIFICATE: 15
IMDB SCORE: 6.8/10
ROTTEN TOMATOES SCORE: 54%

SEX SCORE: 4/5

✔️ Rewatchable – it’s a film that I would stop to watch if it was on TV even if it was already an hour in!
✔️ Definitely want to fuck the cast! Sebastian and Kathryn would definitely be on a list of dream movie threesomes, although that is a long list…
✔️ Yes to fantasies – mainly romantic ones as a teenager when I still believed that bad boys could be fixed by love, but they weren’t all that clean!
✔️ Bechdel test easily passed – lots of named female characters and lots of talk of school and reputation so no trouble with this one.
But is it sex positive?! I’d say no – the villains are sexual and are saved by love. The good are chaste and innocent, and risk being destroyed by sex. Not such great messages… It’s also very homophobic!

As always, this contains spoilers so watch the film before you read on…

STREAMING: Netflix, YouTube (from £7.99), Amazon Prime (cost to be updated), Rakuten TV (from £2.49)

The Cruel Intentions poster, showing conspiratorial faces from Ryan Philippe and Sarah Michelle Gellar as they look down on an innocent looking Reece Witherspoon

If ever I wanted proof that how I first experience a cultural phenomenon changes its lasting impact on me, I need look no further than my first viewing of Cruel Intentions. It was 2000 and I was in year 10. Our classroom was in a separate block designed for language lessons and, in a move that confirms my own privileged upbringing, the language teachers rarely locked the cabinet that contained the video player. So, when someone brought in a VHS copy of Cruel Intentions, we all watched it, and news spread around the block. Soon the classroom was full of fifteen year old girls, sharing chairs and perched on tables as we avidly watched what was by far the sexiest thing I had ever seen.

Not far into the film, our German teacher wandered into the room, pottering in the cupboards at the back and getting out reading materials for the afternoon’s class. You could have heard a pin drop. I don’t think my year group has ever sat so still and so quiet, hoping beyond hope that she wouldn’t notice what we were watching.

This was at the moment of the film where Kathryn and Sebastian are setting out the terms of their wager. No one in the room had seen the movie before so we didn’t know the precise danger waiting just around the corner. Sebastian has agreed that, if he loses and isn’t able to seduce righteous virgin Annette, he’ll give Kathryn his car. And if he wins?

‘I’ll fuck your brains out.’

‘Oh!’ gasps our German teacher, ‘What films you girls watch!’

And she was gone!

Honestly, I struggle to remember another time when almost, almost, being caught doing something naughty felt so fucking good! The adrenaline, the sex on screen, the rush of relief and astonishment that we’d got away with it…it was quite an awakening. And that was before Sarah Michelle Gellar and Selma Blair kiss and before Ryan Philippe gets his arse out and before that iconic scene when Reece Witherspoon is going up that escalator and Philippe appears at the top, all while Counting Crows ‘Colorblind’ is playing, and she says ‘I’m impressed’ and he says ‘Well, I’m in love!’ and my teenage heart exploded.

Of course, my memory must be playing tricks with me. Our lunch break was less than the length of the film and so we can’t have watched it all, and although it’s possible that that same level of sexual tension was maintained over a few days, it feels unlikely. Instead, I can only assume that it’s just this film; it’s hot and always will be and, according to a piece in the Telegraph earlier this year, I wasn’t the only one who felt this way – it seduced a generation!

Describing it as a ‘sexy cinematic firebomb, one dressed up in a blood-red bustier and dripping in quasi-incestuous dirty talk,’ Adam White suggests that this movie, and its subsequent recent comeback with a TV sequel and musical heading to the Edinburgh Fringe Festival this year, taps into ‘our generational thirst for schadenfreude.’ After a soft and sunny 90s filled with dewy-eyed romantic comedies, we were ready for something harder. Something more cynical. And sadly, the future in store for that generation – the much maligned millennials – has proven that it was good to be prepared. Or did this film and how much we enjoyed it, pave the way for today’s call out culture? Both Sebastian’s pattern of only destroying hypocrites and the revelation of Kathryn’s real character in the finale echo our current glee in ‘knocking undesirables off a pedestal of unearned privilege’ and discovering the seedy truth behind anyone claiming to be good.

Philippe and Gellar dresses in black with dark glasses, holding a letter

But cynical extrapolations aside, this film certainly had a huge effect on me as it was just soaked in sex and, importantly for me, sex for my age and generation. Cruel Intentions retold Les Liaisons Dangereuses for a modern audience, with Kathryn Merteuil (Sarah Michelle Gellar) and her step-brother Sebastian Valmont (Ryan Philippe) plotting to destroy the reputation of virginal Annette Hargrove (Reece Witherspoon) by manipulating her into having sex before the new term at school starts.

Somehow the film managed to feel relevant to my life despite the huge gulf between the wealth and sexual experience of the characters and mine. Annette’s struggles with her virginity when faced with love was relatable, Cecile’s naivety clashing with her obvious sexuality was an exaggeration of my own turmoil, and the ongoing, all pervasive obsession with reputation was certainly understandable. The fear at being the person at school that everyone was talking about was almost as strong as the fear of being the one nobody talked about.

But in thinking about this film, I have struggled to decide if it’s sex positive or not, if it was a good example for my teenager self – and my difficulty is mainly due to the identification of heroes and villains. The moral arc of the film clearly defines Kathryn as a villain but the fact that she owns her sexuality and sexual needs feels more sex positive than Annette’s pledge to wait for marriage, eventually downgraded to waiting for love but which is still problematic. Although Kathryn’s manipulation and selfish scheming are undoubtedly (deliciously) evil, it could be argued that if she were allowed to be as sexual as she wanted without damaging her reputation, all of these plots would be unnecessary. As she says, ‘God forbid I exude confidence and enjoy sex!’ and yet as she is dumped for ‘innocent little twots’ who are a more superficially attractive type of women, she has to lie to maintain her chaste and moral reputation. Is this sex positive? I don’t think so!

Sarah Michelle Gellar understood this complex division and recognised the importance of playing this role, inhabiting this sexuality and depicting this type of women. It was her decision to dye her hair a dark brunette, creating a definite split from her blonde, innocent previous roles – most famously Buffy the Vampire Slayer. It would require a whole other long, long essay to unpick the depiction of female sexuality in BVS (and the podcast Buffering the Vampire Slayer does a very good job of this) but I think it’s pretty telling that when Buffy loses her virginity to the man she loves, he loses his soul and becomes the Big Bad of the season. Buffy creator Joss Whedon certainly didn’t understand Kathryn, referring to the film as ‘porny,’ to which Gellar responded that Cruel Intentions was her ‘best work to date.’ Talking to Premiere, she said that ‘brushing it off by calling it ‘a porny’ is unbelievably hurtful to me. He owes me flowers. And that’s on the record.’

Gellar looking hot in her underwear on her bed, trying to seduce Philippe

Because Kathryn is hot. She’s hot and she’s powerful and she’s a seductress and, as much as I’d wanted to end up fucking Sebastian, I secretly but definitely wanted to be her more than I wanted to be the other female characters. I was so jealous of her acceptance and joy to in her sexuality. I was jealous of her confidence and ability to just be sexy. Just as Laura San Giacomo taught me what it was to be sexy in the 80s, Kathryn showed me how to be sexy in my own generation.

A black and white image of Gellar lying back against Philippe

And I believed her that sex was something that everyone was doing, just that ‘no one talks about it.’ Being at an all girls school with staggeringly few male friends, I could completely believe that there was another world just around the corner where All The Sex was happening and I’d have loved it if someone had introduced me to it, as Sebastian does for Cecile.

For me, Cecile’s character is the only one that doesn’t stand up to a rewatch now. She’s too child-like, too naive, and my now adult eyes cringe at her sexualisation. Of course, as a teenager I saw myself in her – at the start of the film, she is definitely a child, wearing T-shirts with big animal prints and doing headstands to impress her crush, but by the end she is an adult, asking for what she wants sexually and owning her fate, and I wanted that arc so much. Kathryn and Sebastian’s aim may have been to destroy her reputation but Cecile’s face at the end as she hands out copies of Sebastian’s journal to her peers suggests that it’s not done her any harm at all in their eyes.

Blair, wearing a koala T-shirt, sat next to Christine Baranski

The importance of maintaining the ‘right’ reputation is, after all, the whole point of the film – Kathryn as a saint, Sebastian as a whore, Greg the gay footballer as a macho straight jock, Annette as a good girl. All of them go out of their way to ensure these reputations aren’t damaged, Sebastian even leaving Annette after Kathryn mocks how much dating the headteacher’s daughter would stop him being seen as a bad boy who fucks around. But this is perhaps the only way that I could take a sex positive view on this film because sex doesn’t actually destroy anyone. It allows Cecile to grow up, it shows Annette that losing her virginity isn’t that big a deal. Even Sebastian learns that sex doesn’t always need to be a weapon. Yes, Kathryn ends the film in tears but it feels more like the lies and manipulation are her undoing.

But despite this, I cannot conclude that Cruel Intentions is sex positive film because of the homophobia. Being gay is definitely a potential source of humiliation and, although Joshua Jackson’s character Blaine was probably the queerest mainstream character I had seen on screen by that point in my life, he’s not a good person and it’s more than a little appalling that he was the queerest mainstream character that I had seen by the age of 15! Roger Ebert found the dismissal of homosexuality to be at odds with the characterisation of these sexual young adults, feeling that ‘kids as sophisticated as those in this story would be less homophobic.’ I, however, feel that it fits perfectly with the sex negative undertones. If having sex full stop could damage reputations, it’s sadly hardly surprising that gay sex is worse.

This movie also introduced me to the connection between sex and power, and who is seen as powerful, although I am less keen on the implication that women can only maintain this power by withholding sex from men – Kathryn is able to use her sexuality as a weapon, wielding her power over Sebastian because she knows how much he wants her, and Annette has a similar amount of power over him, initially because her virginity seen as a challenge and later through love and a wish to avoid disappointing and hurting her.

Of all of them, Sebastian’s character arc is one that I can see much more clearly as an adult. As a teenager, I lusted after his bad-boy-turned-good-by-love sexiness, a very dangerous rom com trope, but I missed the nuance. My now more experienced observation can see pick-up artistry in his moves, initiating touch early, negging, and creating false closeness through manipulating circumstances so they meet often and appear to share interests. He really is a creep! He’s the ultimate fuckboy and not the cold-hearted but misunderstood lothario that I thought he was.

Philippe whispering In Witherspoon’s ear

Teenage me wholeheartedly believed that Sebastian could be ‘fixed’ by love and that he would have been happy with Annette forever. I now know that that’s a lie, sold to us by the romance industry. Kathryn’s bleaker view of his boredom is more accurate and Sebastian’s death was arguably the only good ending for his character. The type of seventeen year old boy who drives a vintage sports car and has a leather-bound scrapbook of his sexual conquests is not likely to stay faithful to his high school love forever, even if he believes it himself. People do change if they want to, but it doesn’t happen overnight.

Maybe that’s why this film seduced my generation so fully. Like reading Catcher in the Rye, you have to watch it as a teenager otherwise the characters all look unbelievable. But if you’re the right age when you see it, it’s overwhelming and seducing and hearing those opening bars of Bittersweet Symphony will unleash a wave of nostalgia for a time when finding Ryan Philippe waiting at the top of an escalator was all I ever wanted.

And that’s it! That’s all I have to say about Cruel Intentions, except for that one scene…

I don’t know that I like it… As much as even my Kinsey 1 straightness really wanted to be taught to kiss by Sarah Michelle Gellar, the male gaze is too strong and has difficult implications. ‘Haven’t you ever practiced on one of your girlfriends?’ fits into the same tired trope as female friends having pillow fights in sexy underwear – unrealistic and unnecessarily sexualising women even when they’re alone.

So Cruel Intentions is not sex positive, it’s pretty homophonic and definitely filmed for a male gaze…but I still fucking love it! It’s hot and it’s one of the personal and generational catalysts for sexual awakening, and it’s just such a great story!

Next week: When Harry Met Sally…

Copyright
All stills and photos are sourced from MovieStillsDB and CineMaterial, and are the courtesy of their respective production studios and/or distribution companies. Images are intended for educational or editorial use only. Gifs from Giphy.com