I identify as a rapidly aging LA bisexual in a stable relationship with a nice guy who brings me coffee when I’m hungover and secretly arranges to get my filthy car cleaned. But there was a time—not so long ago, in fact—when I was a young, messy, newly out lesbian living in Brooklyn and doing my level best to secure a girlfriend in any way possible. I didn’t want just any girlfriend, however; I went on plenty of dates with nice, normal women who held down jobs and paid their taxes and responded to my texts. But the ones who truly held my attention during that mildly insane time of my life were, well…the not-so-sane ones.
Given that I’ve struggled with depression and disordered eating for most of my life, it feels kind of weird and vaguely misogynistic for me to refer to any other woman as crazy, but you have to understand that the C-word was by no means a deal-breaker for me back then; I was absolutely captivated by the dazzling chaos that beautiful, charismatic, mean, possibly under-medicated women let loose in my life (whenever I could actually convince one to return my calls, that is). Then, on a recent Sunday afternoon, it suddenly hit me: Was my type back then more or less just Angelina Jolie as stunningly sexy sociopath Lisa Rowe in the 1999 film Girl, Interrupted?
This is a bold statement, but I’m going to make it: I’m not sure anyone has ever been as well cast as Jolie in that role. Obviously, the actor—who turned 50 today—has dealt with her own share of inner turmoil, public scrutiny, and media bullshit (especially in recent years), so maybe some of her constantly gossiped-about glamour fed into her onscreen portrayal of Lisa. But honestly, revisiting the movie in 2025, it’s amazing how completely Jolie disappears into the role; her Lisa is a total nightmare, to be sure, yet Jolie plays her with enough aplomb, humor, and, yes, seductiveness to make me wonder just how much of my chaotic-girl-chasing 20s was unconsciously inspired by her.
Grateful as I am to be much healthier now emotionally, I still have a soft spot for Jolie’s portrayal of Lisa. Maybe it’s because enough time has gone by since I was obsessively trying to get a second date with girls whose whole deals spanned even more of the DSM-IV than mine did that I can actually look back at that period semi-nostalgically. All I can say now is (1) Girl, Interrupted holds up, and (2) I hope the Lisa-esque women I used to be infatuated with have benefitted from therapy and healing over the years as much as I have. We all deserve it! Especially Angelina Jolie herself!
