Entertainment Weekly has a wonderful oral history of Heathers — with everything from the cast's mutual annoyance with a young ("bitchy") Shannen Doherty ("She didn’t realize it was a comedy, or maybe know what a dark comedy meant") to the unrequited romance between Winona Ryder and Christian Slater ("We never went out! He was dating Kim Walker. And I had, like, such a big crush on him"). There's also talk about the thwarted sequel plans, which, according to Heathers writer Daniel Waters, involved Meryl Streep and a grown-up Veronica Sawyer taking on Washington:
DANIEL WATERS I did come up with this crazy, cockamamy Heathers 2 where Veronica becomes a page for a senator named Heather, played by Meryl Streep. The ending is her assassinating the president and getting away with it — and it’s a good thing.
WINONA RYDER First of all, I don’t know what their problem is with not wanting to make a sequel. I mean, I get that it’s a special movie, and the pressure of a sequel, and it’s a moment in time that you can’t recapture. But my theory was: There are Heathers after high school. And there are Kurts and Rams. Dan came up with: It’s Veronica, years later, she’s in Washington. She’s somehow erased her past. And she’s being blackmailed, there’s like men in suits who know about the Westerberg murders. And I’m like, “What if Christian comes in as the Obi-Wan guy and explains to me…” And I remember the First Lady was Meryl Streep. I’m like, “Guys, this is genius!” Every time I [mentioned it to] Michael and Dan and Denise, they would snicker! Like, “Aww, that’s so cute.” I’m like, “Guys, this is genius! This is such a good idea!”
WATERS I told Winona the idea without any more elaboration than I’m giving you, and a year later I hear from her: “So I talked to Meryl. She’s in!” I’m like, “What?!”
RYDER I was working with Meryl on The House of the Spirits. I was pitching her the whole thing in the makeup chair one day. She was very sweet about it, and she was like, “Oh, that sounds really great!” But what else are you going to tell a panting 19-year-old? She could’ve been just waiting for me to shut up. [Laughs] You have to understand: We were in rural Portugal living in huts, playing Chilean refugees. There were only dirt roads. I’m like, this looks like those Agnes B ads —you know where they’re in a field and there’s a farmer with like a pitchfork?