Hilary Duff as Sam Warner Bros. Pictures, Jon Kopaloff / Getty Images Then: Diner girl.Now: Star of Younger, mom of two. Chad Michael Murray as Austin Warner Bros. Pictures, Noel Vasquez / Getty Images Then: Idiot teen who couldn't tell Hilary Duff's identity underneath a teeny tiny eye mask. Now: Playing a cult leader on Riverdale. Jennifer Coolidge as Fiona Warner Bros. Pictures, Angela Weiss / AFP / Getty Images Then: Evil stepmother.Now: Honestly, a living icon. Recently graced Ariana Grande's "thank u, next" video with a cameo. Regina King as Rhonda Warner Bros. Pictures, Angela Weiss / AFP / Getty Images Then: An actual fairy godmother.Now: A true legend who just won an Oscar for her incredible performance in If Beale Street Could Talk. Julie Gonzalo as Shelby Warner Bros. Pictures, Paul Archuleta / Getty Images Then: High school mean girl. Now: Julie has appeared in lots of Hallmark movies, as well as a 2018 episode of Grey's Anatomy. Dan Byrd as Carter Warner Bros. Pictures, Eike Schroter / Walt Disney Television via Getty Then: Trusty sidekick.Now: Starring on the upcoming Amazon Prime drama series, Utopia. Madeline Zima as Brianna Warner Bros. Records, Paul Archuleta / Getty Images Then: Evil stepsister No. 1. Now: Still acting in movies and appeared in the Twin Peaks reboot. Andrea Avery Ray as Gabriella Warner Bros. Pictures, Facebook: profile.php Then: Evil stepsister No. 2. Now: Andrea's last IMDb credit is from 2005, but she still acts in a lot of theater productions. Mary Pat Gleason as Eleanor Warner Bros. Pictures, Michael Tullberg / Getty Images Then: One of diner gal's diner pals!Now: Has recently appeared in Will & Grace, Mom, and the Netflix movie Sierra Burgess is a Loser. Simon Helberg as Terry Warner Bros. Pictures, David Livingston / Getty Images Then: Played the role of this dude in the movie.Now: Maybe you heard of his little project called The Big Bang Theory???