What The “Heathers” Cast Looked Like Then Vs. Now

4. Christian Slater – Jason ‘J.D.’ Dean

Along with Winona Ryder and Shannen Doherty, Christian Slater’s career path in Hollywood took a distinct upswing following his starring role in Heathers. After attracting attention playing the charismatic, rebellious, and extremely troubled Jason “J.D.” Dean, who moves to Westerburg following his mother’s suicide and uses some extremely violent methods to deal with the crew of popular students who run the school, Slater went on to play similarly troubled characters in movies like 1990’s Young Guns II and Pump Up the Volume. He soon achieved superstardom with parts in Robin Hood: Prince of Thieves, Untamed Heart, and Interview With the Vampire.

Since the early 2000s, Slater has primarily booked supporting film roles and focused on TV work. You may have spotted him in The West Wing or remember him as Alex Donovan in the ABC crime drama The Forgotten. He’s also done quite a bit of voicework in recent years, lending his pipes to characters on Archer, Robot Chicken, The Lion Guard, and others. His most recent project is the popular USA thriller series Mr. Robot, in which he has played the title character since 2015.

5. Winona Ryder – Veronica Sawyer

At Westerburg High, the “Heathers” rule, and the formerly unpopular and brainy Veronica Sawyer (Winona Ryder) is their newest member. The other Heathers are rich, snotty, and particularly cruel to many of their classmates. When Veronica decides she’s had it with their behavior, the other Heathers turn on her. As the rebellious new student J.D. starts shaking things up among the social circles at Westerburg, Veronica finds herself infatuated with him and inadvertently drawn into his plans—until she realizes just how dark they are.

Along with her appearance as Lydia Deetz in 1988’s Beetlejuice, Ryder’s role as Veronica in Heathers helped launch her to superstardom. She’s since gone on to appear in a number of acclaimed films, including in Edward Scissorhands, Reality Bites, Little Women, A Scanner Darkly, and Girl, Interrupted. More recently, Ryder has enjoyed a career resurgence with her role as Joyce Bowers in the Netflix original series Stranger Things, and she’s slated to star alongside Keanu Reeves in the upcoming rom-com Destination Wedding.

6. Penelope Milford – Pauline Fleming

While the teachers of Westerburg High are mostly backgrounded characters in Heathers, one stands out for her eccentricity and her actual interest in the students’ well-being: Ms. Pauline Fleming (Penelope Milford). Westerberg’s caring guidance counselor is often made fun of by the students—who call her “Miss Phlegm”—and derided by her colleagues for her hippy-dippy ways. After the second “suicide” strikes their school, Pauline has decided she’s done taking guff from the other teachers and lashes out at them for trying to play “another round of ‘Let’s Laugh at the Hippie.'” Later, she leads the student body in a grief-sharing session in the school cafeteria following the deaths of Kurt Kelly and Ram Sweeney.

For actress Penelope Milford, her part as Ms. Fleming in Heathers came toward the end of her relatively short Hollywood career. Milford rose to fame in 1978 for her part as Vi Munson in Coming Home, for which she received an Academy Award nomination for Best Supporting Actress. Milford also was quite active in the theatre and originated the role of Jenny Anderson in the 1975 Broadway musical Shenandoah. Following Heathers, Milford has only had a handful of screen appearances—her last major supporting part was in the 1996 crime drama Normal Life, alongside Ashley Judd and Luke Perry. Today, Milford lives a quiet life in New York’s Hudson Valley region, spending her days on hobbies like researching local history. In 2013, she came out of her acting retirement in to appear in a production of Harold Pinter’s one-act play A Kind Of Alaska at the Cocoon Theatre in Rhinebeck, New York.