Fifteen years ago today, teenagers around the world gathered in awe at the release of Cruel Intentions, which featured Buffy the Vampire Slayer as a villainess who said lines like “you can put it anywhere,” and launched Ryan Phillippe to teen idol status even though no one was ever quite sure how to pronounce his name. Phil-ip-pee? Phil-eep? Anyway, given the film’s titanic impact in 1999, it’s amazing what a rough road its cast has endured since then.

Written and directed by Roger “Who?” Kumble, Cruel Intentions was one of many teen films inspired by serious literature, in this case the epistolary French novel Les Liasons Dangereuses by Pierre Choderlos de Laclos (more likely, Kumble saw Glenn Close and John Malkovich in 1988’s Dangerous Liasons and was struck by how much they acted like teenagers). Phillippe and Sarah Michelle Gellar are Sebastian and Kathryn, a pair of worldly rich step-siblings on the Upper East Side toying with hearts for their own petty amusement. A callous bet that Sebastian can rob new girl Annette (Reese Witherspoon) of her virginity leads to a doomed romance, public disgrace, death by taxicab, etc. etc. etc.

It was all very scandalous in 1999, with Gellar (only known as the wry WB hero Buffy) snorting cocaine out of a crucifix necklace and Phillippe baring his ass to catapult himself into the hearts of many youngsters; his long relationship with Witherspoon also began on-set. Back then, this was a stacked cast with bright futures in Hollywood; now, they’ve had some success, mixed in with a lot of public, spectacular failure. How does everyone stack up, then and now? Note: unlike our Reality Bites list, we’re talking real-life careers, not fictional character outlooks.

Cruel Intentions cast power rankings (1999)

1. Sarah Michelle Gellar (as Kathryn Merteuil)

Cruel Intentions came out in March 1999. Gellar was the star of Buffy the Vampire Slayer, which was riding high in the middle of its third and arguably best season (the final year in high school, with Faith and the Mayor and all that jazz). Gellar has the best role in Cruel Intentions, dispensing acrid bon mots and making out with Selma Blair for no good reason (she won MTV Movie Awards for Best Performance and Best Kiss). Sure, she gets a villain’s comeuppance, but who’s really rooting for boring goodie two-shoes Reese Witherspoon?

2. Ryan Phillippe (as Sebastian Valmont)

Much like Gellar, Phillippe had a pretty limited film resume before showing up in Cruel Intentions—the biggest movie either appeared in before 1999 was I Know What You Did Last Summer. But Phillippe was building up serious steam with frosted, blond, Timberlake-esque tips and solid appearances in (underwhelming) films like 54 and Playing By Heart. Plus, he met his wife and the future mother of his children on set! Things were looking swell.

3. Reese Witherspoon (as Annette Hargrove)

Reese’s boring role in Cruel Intentions was balanced out by her much peppier performance in Pleasantville the year prior; Election also came out later in 1999, netting her oodles of critics awards. She wasn’t quite as teen-famous as Phillippe or Gellar at this point, but her star was quickly rising off a solid teen actress career including films like Fear, Twilight and Freeway.

4. Joshua Jackson (as Blaine Tuttle)

I hope you didn’t all forget Jackson’s scene-stealing work as Blaine, the catty gay college student who gleefully helps Sebastian blackmail closet cases in exchange for drugs. Dawson’s Creek was only in its first season at this point, but it was already a sensation, and in case you forget, Jackson was also in all three Mighty Ducks movies and Urban Legend before this. Solid.

5. Selma Blair (as Cecile Caldwell)

Kumble cast Blair, a relative unknown who coincidentally came close to landing the lead role in both Buffy and Dawson’s Creek, after she apparently nailed Cecile’s entitled bitchiness in her audition. Blair was all potential at this point, but there’s no question Kumble was right to vault her to stardom. She was on the receiving end of that SMG kiss, too, so she was a dominant presence in the minds of frustrated teenage boys who hadn’t figured out how to find porn on the internet yet.

6. Tara Reid (as Marci Greenbaum)

It’s important to note just how much better pretty much everyone was doing in 1999. In the present day, a bottom of the list ranking indicates true disaster; but back in 1999, Reid was doing pretty okay. Her role in Cruel Intentions is very small—she’s screwed over by Sebastian in the opening scene to show how dastardly he is—but she’d also been in The Big Lebowski and Urban Legend, and American Pie was right around the corner.

Cruel Intentions cast power rankings (2014)

1. Christine Baranski (as Bunny Caldwell)

This isn’t even close. While every other cast member in Cruel Intentions has experienced some kind of professional or personal turmoil in the intervening years, Baranski (who played Selma Blair’s kinda-racist mom) has just gone from strength to strength. And she was already Christine Baranski, Broadway star, two-time Tony Award winner for The Real Thing and Rumors, and Emmy winner for Cybill. Since Cruel Intentions, she’s best-known for her work on The Big Bang Theory (two Emmy nominations) as Leonard’s mom and her stellar role on The Good Wife (four more Emmy noms) as the fearsome, smart, amazing Diane Lockhart. Christine Baranski is the best.

2. Joshua Jackson

Sure, Josh’s career maybe never quite hit the heights some teen TV stars later enjoy. Dawson’s Creek wrapped up in 2003 and Jackson bounced around crappy indie movies and a stint on the West End before getting cast as Peter Bishop in Fringe. Hopefully Jackson has finally realized that TV is the place for him, and his solid work for five years on a cult sci-fi show has given him a whole new devoted section of fans (his new Showtime show The Affair debuts later in 2014). Plus, he’s been in a relationship with Diane Kruger since 2006, and by all indications the two are very happy.

3. Sarah Michelle Gellar

It’s been a real up-and-down world for ol’ SMG ever since Buffy left screens 11 years ago. Her film career had some solid financial successes (Scooby-Doo, The Grudge, uh, that’s about it) but even the moneymakers were poorly received, and there’s a lot of forgettable genre and indie trash littering her resume. Props, though, for her funny work on underrated bonkers Richard Kelly flick Southland Tales. Teen horniness is not a crime. SMG basically gave up on movies after 2009 and jumped back to television, where her first effort Ringer came and went in 2011, best known for the worst green screen of the century. Her current role on hit CBS sitcom The Crazy Ones is pretty thankless, but it looks like a safe bet to get picked up for a second season. Can’t complain, really. She married Scooby-Doo co-star Freddie Prinze Jr. in 2001 and has two kids with him.

4. Reese Witherspoon

Now, it’s important to note: Reese Witherspoon is the only name on this list that is a no-kidding movie star. The lady has an Oscar (for her understated work as June Carter in Walk the Line), she was in some serious hits (Sweet Home Alabama, Legally Blonde, Four Christmases), and she commanded $15 million a picture as recently as 2010 (for James L. Brooks’ epic flop How Do You Know). At the same time, she’s undergone some…personal turmoil. She divorced Ryan Phillippe in 2007, dated Jake Gyllenhaal for a couple years, and since married agent Jim Toth, who was driving with a blood alcohol of 0.139 when they were pulled over by cops and she threw an epic celebrity fit. Her career has really nosedived as of late, too, something Witherspoon ascribed to there being “a lot of really, really, really big movies about robots and things” that had no place for a 30-something actress. Maybe she can bounce back in 2014 with roles in Wild (based on the Cheryl Strayed book) and Inherent Vice.

5. Selma Blair

One of the biggest counts against Selma is also one of the biggest entries in her “pro” column. On the one hand, she was fired from crappy FX sitcom Anger Management, which is pretty embarrassing. On the other hand, she was fired because she criticized Charlie Sheen, who decided that he hated her as a result. That’s a badge of honor. Plus, she was in Hellboy AND Hellboy II: The Golden Army, underrated superhero movies, and she was the only actor Kumble retained for his follow-up effort to Cruel Intentions, The Sweetest Thing, where Blair helped sing “The Penis Song.” That’s pretty much a ticket to immortality right there.

6. Ryan Phillippe

Poor Ryan. Remember when he presented an Oscar with then-wife Reese, and he let her read the winner envelope, quipping, “you make more money than me”? That’s pretty much his career high point since Cruel Intentions. He was incongruous and kinda bad in the otherwise excellent Gosford Park, he had a forgettable roles in Oscar-winner Crash and Clint Eastwood war epic Flags of our Fathers, he did solid work in the little-seen (but very good) thriller Breach. Recently, he’s toyed with his former teen idol image for comedies like MacGruber and The Eric Andre Show, but it’s not enough to have him stand out of the pack. In his personal life, he knocked up model/actress Alexis Knapp.

7. Tara Reid

Oh, God. Don’t make me do this. Let’s just say 2013’s Sharknado was considered a healthy comeback for poor Ms. Reid. Look out for her in 2014’s Sharknado 2: The Second One. Keep at it, Tara.