Cruel Intentions
Credit: Everett Collection

I Love the '90s

The messed-up machinations of bored, oversexed stepsiblings Kathryn Merteuil and Sebastian Valmont aren't quite as shocking in 2014 as they were when Cruel Intentions was released on March 5, 1999. (Blame Gossip GirlPretty Little Liars, and a zillion other glitzy/scandalous imitators.)

That said, Cruel Intentions is still an enormously entertaining teen movie, even 15 years (gulp) after its initial release — thanks to an uncommonly sharp script, a killer soundtrack, and, most importantly, an impeccable cast, which featured future Oscar winners and future Sharknado stars alike. Well, one of each, but you get the picture. Whoever headed up this franchise had a serious eye for talent: One of five-time Academy Award nominee Amy Adams' first roles was as the lead of a spin-off TV show that never made it past the pilot stage and was subsequently marketed as Cruel Intentions 2. NEVER FORGET.

But back to the original. Cruel Intentions' pretty young things — the interesting ones, anyway — spend the film's 97-minute run time both screwing with each other and being screwed with. By the final frame, the status quo established at the beginning of the movie has been turned on its head: reformed bad boy Sebastian (Ryan Phillippe) is dead, while good girls Annette and Cecile (Reese Witherspoon and Selma Blair) have triumphed over alpha bitch Kathryn (Sarah Michelle Gellar, never better). In real life, though, basically everyone affiliated with the movie came out a winner: All went on to find some degree of stardom on screens big and small, and most are still fairly relevant today.

Of course, some are a little bit more relevant than others. Which is why I'm taking this opportunity to reevaluate the careers of the Cruel Intentions gang in a modern context. Who ended up being the cast's real Queen Bee — and who basically got dumped by Hollywood over Fourth of July weekend? The answers may surprise you!

12. Charlie O'Connell (Court Reynolds)

Blink and you'll miss Jerry's brother as the jock who indirectly gets the plot of Cruel Intentions moving when he ditches Kathryn for Cecile. Blink again, and you'll miss O'Connell's appearances in things with names like 2-Headed Shark Attack and Kraken: Tentacles of the Deep. Oof. (He was also the titular Bachelor in the seventh season of ABC's reality hit, but I don't think that should count as a career high.)

11. Tara Reid (Marci Greenbaum)

Congrats, Tara — you're not last! But that's only because Sharknado ended up being a weird viral phenomenon instead of just another disposable Syfy disaster movie. Come see us after Sharknado 2: The Second One; then we'll talk.

10. Selma Blair (Cecile Caldwell)

Poor Selma. I'll always have a soft spot for her, mostly because my 11-year-old self thought the way Cecile said "Want company? Want a blow job?" was the funniest thing ever. (Note: Do NOT let your 11-year-old siblings/nieces/nephews/children watch Cruel Intentions.) And yet since the early aughts, she's been stuck in one disappointing project after another, Hellboy notwithstanding. Blair deserves better than Anger Management and Kath & Kim, but for whatever reason, she's just not getting those better parts — so as much as this breaks my heart, I've got to leave her at No. 10. She'll have to console herself with a few iced teas. (They're from Long Island.)

9. Ryan Phillippe (Sebastian Valmont)

He started out the aughts with big roles in sophisticated fare like Gosford Park and Igby Goes Down, and as half of every millennial's aspirational super couple. (Ryan and Reese were a younger, cooler version of Brad and Jen.) Then Phillippe and Witherspoon split… and Ryan started getting stuck in dreck like MacGruber. Could ABC's murder drama Secrets and Lies, currently in the pilot stage, help Ryan raise his profile? It's possible — but if the show's as bland as its title, it'll be nothing to write in your meticulously detailed sex diary about.

8. Eric Mabius (Greg McConnell)

The future Ugly Betty star had a small role in Cruel Intentions as a closeted football player. Since then, he's done Betty (good!), The L Word (fine!), and a bunch of TV movies and guest roles (meh!). Not embarrassing, but not exactly setting the world on fire.

7. Louise Fletcher (Helen Rosemond)

Remember when I said Cruel Intentions featured a future Oscar winner? Well, it also featured someone who had already won Best Actress: Louise Fletcher, star of One Flew Over the Cuckoo's Nest. (Fletcher played Sebastian's aunt, who's barely in the movie.) The more you know! Anyway, Fletcher's career clearly didn't reach another high point after Cruel Intentions, unless you count a guest role on 7th Heaven. Even so, I've got to give her some credit — if only for continuing to find steady work in a town that prefers to pretend women over 40 don't exist.

6. Sean Patrick Thomas (Ronald Clifford)

One of the kings of millennial teen movies — with Can't Hardly Wait and Save the Last Dance, as well as Cruel Intentions, under his belt — scored some modest success with CBS' The District and the Barbershop movies, but he's been nearly invisible onscreen in the past few years (unless you count an arc on Gellar's ill-fated Ringer). That's too bad. He is, however, co-starring in this spring's Broadway revival of A Raisin in the Sun, opposite Denzel Washington. That's good! Come back to us, Sean! Teach us how to dance again!

5. Joshua Jackson (Blaine Tuttle)

Jackson's crowning achievement as an actor would come just one year after Cruel Intentions, when he starred as scrappy Luke McNamara in The Skulls. Yet even in the 14 years between then and now, he's done a lot of good work on TV — first while serving out his term as the best thing on Dawson's Creek, then as the sardonic voice of reason on the beloved cult series Fringe. He may not shine as brightly as his luminous longtime girlfriend Diane Kruger, but his Showtime pilot The Affair could be promising — and either way, his 2010 Pacey-Con prank makes Jackson a permanent winner in my book.

4. Swoosie Kurtz (Dr. Greenbaum)

Fun fact: Before playing Sebastian's therapist in Cruel Intentions, Kurtz played Cecile's mother in the 1988 Glenn Close/John Malkovich Dangerous Liasons. Callbacks! Kurtz has also racked up two Tony nominations and two Emmy nominations since Cruel came out, in addition to starring in a short-lived instant cult classic series (Pushing Daisies) and getting a steady gig on CBS' Mike and Molly. Between that stuff, the legacy of her theater work, her role on the 1990s series Sisters, and memorable performances in earlier films like Citizen Ruth and Liar Liar, Kurtz's reputation is doing just fine.

3. Sarah Michelle Gellar (Kathryn Merteuil)

Buffy will always give Gellar a sort of lifetime pass. But after her beloved Joss Whedon series ended, Gellar fell into a bit of a slump — thanks both to big-screen bombs like Southland Tales and Happily N'Ever After and her much-hyped, short-lived CW series Ringer. Thank goodness, then, for The Crazy Ones, which does relatively well on CBS even if it isn't a huge hit. If nothing else, it's putting Gellar back into the conversation — which is certainly worth something.

2. Reese Witherspoon (Annette Hargrove)

Between ElectionLegally Blonde, and, oh yeah, her Oscar for Walk the Line, it may seem nuts not to stick Reese in the No. 1 spot. And yet. And yet! Between How Do You Know, Water for Elephants, and This Means War — not to mention her disorderly conduct arrest — the last few years have been kind of a mess for Reese. Come to think of it, the years before weren't so great either. (Four Christmases, anyone?) With Inherent Vice and Wild in the pipeline, things could be looking up for Witherspoon fairly soon… but for now, I'm reluctant to name her the unequivocal winner of Cruel Intentions.

1. Christine Baranski (Bunny Caldwell)

Hear me out on this: Baranski is a national treasure. She's one of those actors who has the power to elevate any project single-handedly, including stinkers like How the Grinch Stole Christmas! And because she's more of a character actress than a glamorous, A-list leading lady type, she doesn't share the same burdens that Witherspoon does — which means she'll always get to be the best part of a bad thing rather than being tainted by a movie or TV show's failure. And then there's Baranski's performance on The Good Wife, widely recognized as one of the best dramas on network TV — between that and her guest turns on The Big Bang Theory, Baranski's garnered six Emmy nominations since 2009.

In conclusion: It's true that in a toe-to-toe battle for Hollywood supremacy, 2004 Reese Witherspoon would easily dominate Baranski. But given Reese's recently tarnished legacy, at this specific moment in time, Baranski is the Cruel Intentions alumna who truly comes out on top — even if she never actually attended Manchester Prep. QED.

I Love the '90s
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