Drew Barrymore as Josie Geller
Since then: Drew continued dominating for a long while after this, with films like Charlie's Angels and 50 First Dates. She also directed her first feature (Whip It) and has done a lot of producing.
Michael Vartan as Sam Coulson
Since then: He spent the early '00s on Alias, and has since bounced around a number of other series, including Hawthorne, Bates Motel, and Satisfaction.
Leelee Sobieski as Aldys
Since then: Eyes Wide Shut followed closely after Never Been Kissed. Stops between then and now: The Wicker Man, Public Enemies, and NYC 22.
David Arquette as Rob Geller
Since then: There were some Scream sequels, of course. Also: Pushing Daisies, Cleaners, Jack and the Never Land Pirates, and Pee-Wee's Big Holiday.
Jeremy Jordan as Guy Perkins
James Franco as Jason
Since then: Well. Uh. Yeah. He's been James Franco. The very distilled version: A little show called Freaks And Geeks, a supporting role in the original Spider-Man movies, the perrennial classic Tristan + Isolde, and a guest-starring spot on The Mindy Project. I'm sure he fit some other things into that time, too.
Jessica Alba as Kirsten
Since then: Pretty much everything people actually remember about her career. Including, of course: Dark Angel, the Fantastic Four movies, Into the Blue, Sin City, and a mighty business empire with Honest.
Marley Shelton as Kristin
Since then: She starred in the severely underrated cheerleader bank robbery movie Sugar & Spice. There was also Bubble Boy, Uptown Girls, Eleventh Hour, one episode of Mad Men, and The Lottery.
Molly Shannon as Anita
Since then: Well, for one, more Saturday Night Live happened. Also: The iconic Superstar, Wet Hot American Summer, and a whoooole lot more. May we never lose Molly Shannon.
Jordan Ladd as Gibby
Since then: There's The Perfect You, Cabin Fever, and a big run on Robot Chicken. She's also got six upcoming projects listed on IMDB, so she's not going anywhere.
John C. Reilly as Gus
Since then: There was that ironically memorable performance as Mr. Cellophane in Chicago, of course. There was also Talladega Nights, Wreck-It Ralph, Step Brothers, and many more.
Cress Williams as George
Since then: There were memorable arcs on Grey's Anatomy and Friday Night Lights; there was also the entirety of Hart Of Dixie, on which he played charming mayor Lavon Hayes.
Octavia Spencer as Cynthia
Since then: Oh, you know, just casually winning Oscars. Octavia took one home for The Help, and has also made memorable turns in Snowpiercer, Red Band Society, and Mom.