You could easily divide Drew Barrymore's career into two parts. In the first part she was your prototypical child star: there was an initial period of cuteness and then there was a protracted period of bad behavior. She was adorable in E.T. at seven, but she was snorting cocaine at thirteen. She was so out of control that she could write an entire biography called "Little Girl Lost" before she was old enough to legally drink.
Now, of course, we see Drew Barrymore very differently. In the last twenty years she's been cast mostly as daft-but-likeable sweethearts in rom-com after rom-com. It's been such a long time since she seemed like a troubled teen that it's easy to forget that she was ever a wild child. Which is why it's so strange to watch her in Poison Ivy now, because this movie is built around the idea that Barrymore's Ivy is a menacing homewrecker.
Poison Ivy is about a lonely teen named Sylvie who makes friends with a bad girl named Ivy after they meet accidentally in the principal's office. When Sylvie finds out that Ivy's home life is very unstable, she invites her to move into a spare bedroom in their luxurious house. At first things are perfect, but Sylvie slowly grows suspicious of hew new "sister", who is a little too eager to fit into her new family. At first Sylvie's concerns just seem like paranoia or jealousy, but eventually her suspicions are confirmed as Ivy's true colors come through, leading to a violent showdown in the pouring rain.
This movie was released the year after Little Girl Lost, so casting Barrymore made sense - the audience would have brought a set of expectations into the theater that would have helped this ridiculous thriller seem more plausible. But there's a reason why Drew Barrymore isn't known for playing this type of character now: she just isn't a natural fit for sexpot murderer roles. She tries her hardest to look like the sort of person who could push someone off a balcony, but it just doesn't jibe; not only does she come off like a nice person throughout the entire movie, but she was so convincing in the scenes where she was searching for a substitute family that her sudden (and mostly unexplained) decision to murder them makes no sense.
Barrymore's miscasting unbalances the whole movie, basically. The plot is supposed to be about a usurper who sneaks her way into a family and then betrays them for selfish reasons, but it's actually about a lonely girl whose gotten kicked around by life who then gets kicked around by a family that has it all and doesn't want to share. It's meant to be erotic and daring, but Barrymore's inability to be a femme fatale turns into kitsch.
Still, the miscasting is compelling in a certain way, because it raises a question: is there any actress who could conceivably nail both a femme fatale role and an America's sweetheart role? Obviously Barrymore is only credible as a sweetheart, but there has to be someone who could do both, right?
My first thought was Charlize Theron, because she's a great actress with great range, and she played a lot of beautiful but helpless wives in her early career before she became an ass kicker in her later career. But those early supporting roles don't really say much about who Theron is now; no, her personality has been defined by her toughness ever since she won an Oscar for Monster. These days she when she plays a romantic part she still gets to carry some guns and be a bad-ass.
Another thought I had was Reese Witherspoon, since she tends to do her best work in roles that blend sweetness with steeliness. But I can't imagine her pulling off the Ivy part, either, probably because she was in a "naive kid is threatened by the person she was trying to help" movie, and she was perfect as the victim. No, she's a sweetheart at heart.
As I was going through the list in my head, I hit wall after wall. (Sigourney Weaver is both sexy and tough, but at the end of the day she's always going to be the bad ass lady who went toe to toe with the queen alien before calling her a bitch and kicking her out into space. And I don't even really want to get into Sandra Bullock, whose Miss Congeniality is trying to do both at the same time, but which I've never seen because it looked awful.) I didn't think I was going to find anyone who could bridge the divide - but then I found the answer: Catherine Deneuve.
In case you aren't familiar with her work, I should explain: Deneuve was great as a doe-eyed beauty in the French film the Umbrellas of Cherbourg but she was also perfect as a heartless vampire in the Hunger. She even managed to be a sweet natured multiple murderer in Roman Polanski's Repulsion, which is kind of an astonishing feat when you think about it. If there's anyone who has ever been able to toggle back and forth between being a black widow who might murder a man and a helpless waif who needs a strong man to protect her, it's Deneuve.
After seriously considering Deneuve's resume, I came to the conclusion that the reason why she is better prepared to switch back and forth between those two extremes is not because she's a better actress than all of the other candidates I mentioned, it's because she's French. Because she doesn't steadily pop up in American movies she has a lower profile and thus she brings less baggage to the table. Since I don't have ingrained assumptions about what type of part she's going to play then there isn't any cognitive dissonance when I see her playing a stone cold killer instead of a delicate paramour or vice versa.
Which makes me think that Poison Ivy's ultimate problem was not that it cast Drew Barrymore - it's that it cast Drew Barrymore because it wanted to piggyback on top of all the baggage she brought with her. Now that all of her teen drama has been out of the public's memory for decades she's lost that baggage, so her presence in this movie makes no sense - which is not something you want to say about the movie's titular character.
Ultimately, however, casting a non-poisonous person as Ivy in Poison Ivy is just the ironic cherry on top of a lot of other laughable touches. (Let's just say that there's a lot of silly 90's fashion in this movie and leave it at that.) So perhaps Barrymore was actually perfect for the role, because it's not like an early 90's thriller about a devious teenage sexpot was ever going to age well - maybe it's best that their lead actress inadvertently leaned into the plot's goofiness. That said, there is always going to be at least one level where Barrymore's mistcasting is still kind of a bummer: it does make me wish for a 90's movie where Julia Roberts was stone cold cold murdering suburban families, but I'm never going to get that.