It's been 17 years since Cruel Intentions made us fall in love and broke our hearts. Long before Gossip Girl, this classic film exposed the sexy and complicated lives of Manhattan's overprivileged teens.

Reese Witherspoon plays Annette Hargrove, the new principal's daughter, who is resolute in her desire to stay a virgin. She also wants to stay away from the school's bad boy, Sebastian, but everything is thrown out of balance when Sebastian is nothing like she anticipated, and she ends up falling for him.

In the past two decades, Reese Witherspoon has taken Hollywood by storm, and has both an Oscar and Golden Globe to prove it. Among her credits are some films you've probably heard of, including Legally Blonde, Walk The Line, and Wild. She also started Pacific Standard, a production company focused on female-driven media, like Witherspoon's most recent project, HBO's Big Little Lies.

Ryan Phillippe stars as Sebastian Valmont, the troubled bad boy, who makes a bet with his stepsister to see if he can seduce Annette and get her to break her vow of chastity before the summer's end. These shenanigans ultimately (SPOILER ALERT) lead to his tragic death. But what is Ryan up to now?

Tragedy becomes Ryan Phillippe, who is still playing characters as dark and dramatic as Sebastian. His most recent roles are an accused sexual assailant on Damages and a murder suspect on Secrets and Lies. Next up is the USA series Shooter, about an ex-marine who's forced back into action after he hears about a plot to murder the president.

Sarah Michelle Gellar plays the wickedly sexy Kathryn Merteuil, whose main goal is to destroy and corrupt all those around her. Unfortunately for her, her stepbrother Sebastian's journal of all their exploits is exposed after his death. Oops. But what's SMG doing these days?

Sarah Michelle Gellar has ruled the TV screen since 1996, so it only makes sense that she'd eventually come to reprise her Cruel Intentions role of Kathryn on the small screen. Although the NBC pilot wasn't picked up to series, it's still in contention for a possible mid-season premiere. Fingers crossed! We would love to see what kind of havoc Kathryn is still wreaking almost 20 years later.

Selma Blair plays Cecile Caldwell, a clumsy, bumbling, insecure, cello-playing freshman. But you probably remember her as the girl who learned how to French kiss with Kathryn in the middle of Central Park. At least, that's what we remember best...

Selma Blair has left her innocent days behind her and is playing some seriously grown-up roles. Her credits include the fan favorites Legally Blonde, Hellboy and Charlie Sheen's Anger Management. But we love her most recent role, portraying Kris Jenner in FX's highly addictive American Crime Story: The People v. O.J. Simpson.

Sean Patrick Thomas plays Cecile's lovelorn cello teacher, Ronald. But he's fired when Cecile's overbearing mother finds out he's secretly been sending her love letters. All orchestrated by Kathryn, of course. Yikes.

Sean Patrick Thomas has had nothing but luck in the past two decades. With more than 40 credits to his name, he's been working nonstop. He even had the fortune of working with castmate Sarah Michelle Gellar on her CW show, Ringer. You can see him next, reprising his role of Jimmy James in the new Barbershop: The Next Cut.

Joshua Jackson plays the loud-mouthed, crass, and openly gay Blaine, who helps Sebastian in his attempts to woo Annette. But what's Josh up to now?

After finding huge success on the wholesome Dawson's Creek as Pacey Witter, the black sheep who finally gets the girl, Joshua Jackson has remained a staple on the small screen. And we are grateful for it! First, he starred as sci-fi skeptic Peter Bishop on Fringe. Now he's Michelle Monaghan's depressed and drug-addicted ex-husband on The Affair.

Christine Baranski plays Mrs. Caldwell, Cecile's social-climbing and fairly racist mother, who fires Ronald after discovering he and her daughter are romantically involved. But what has she been up to since then?

Christine Baranski keeps busy, with 74 credits and two Golden Globe nominations under her belt. She killed it on The Good Wife as Diane Lockhart, a strong-willed law firm partner who championed women's rights. She's been nominated for a primetime Emmy for this role each of the past six years, and CBS just greenlit a straight-to-series spin-off for her character, which is expected to premiere this fall.

Tara Reid makes a brief appearance as Marci, Sebastian's therapist's daughter, who he somehow convinces to pose naked for him. And somehow those naked pictures end up on the internet. Whoops! Has Tara Reid been making better decisions than her character since those days?

Yes! After a string of unsuccessful films, Tara Reid has made a comeback in a big way, starring as April Wexler in SyFy's immediate cult classic Sharknado and its three sequels. The latest, Sharknado: The Fourth Awakens, premieres later this summer!